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4347210-27749500Kurdistan Regional Government-Iraq Ministry of Higher Education and Scientific Research University of Salahaddin College of Science – Department of Chemistry Determination of Cyanide

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4347210-27749500Kurdistan Regional Government-Iraq
Ministry of Higher Education and Scientific Research
University of Salahaddin
College of Science – Department of Chemistry

Determination of Cyanide, Thiocyanate and Pyridine Derivative Compounds Basing on the K?nig Reaction
Submitted to the Department of Chemistry
College of Science – Salahaddin University – Erbil
A Review article
In
Organic Chemistry
By
Trifa Khalaf Mohammed
Supervised By
Asst. Prof. Dr. Rebwar Omer Hassan
June -2018
Determination of Cyanide, Thiocyanate and Pyridine Derivative Compounds Basing on the K?nig Reaction
Abstract
Cyanide compounds have many applications in various industries, these industries discharge large amounts of cyanide contained in their wastewater to the environment which can be dangerous for human life. Thiocyanate is also formed biologically from the detoxification of cyanide, it is less toxic than cyanide but more stable and thus more difficult to destroy, therefore, the cyanide, thiocyanate and pyridine detection is important for monitoring and controlling its toxicity. This article describes the some analytical method are typically based on k?nig reaction for cyanide, thiocyanate and nicotinic acid measurement in different matrices ranging from drinking water and wastewater, to cigarette smoke and exhaled breath to biological fluids like blood, urine and saliva.

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Keyword: Cyanide, Thiocyanate, Pyridine, K?nig reaction, Analytical method.
1.IntroductionK?nig reaction was one of the first wide-spread methods to analyze cyanide, thiocyanid and nicotinic acid. The initial use of the K?nig reaction for cyanide detection evolving by Aldridge in the mid 1940’s ADDIN EN.CITE ;EndNote;;Cite;;Author;Aldridge;/Author;;Year;1944;/Year;;RecNum;55;/RecNum;;DisplayText;(Aldridge, 1944, Aldridge, 1945);/DisplayText;;record;;rec-number;55;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1524374700″;55;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Aldridge, W_ N;/author;;/authors;;/contributors;;titles;;title;A new method for the estimation of micro quantities of cyanide and thiocyanate;/title;;secondary-title;Analyst;/secondary-title;;/titles;;periodical;;full-title;Analyst;/full-title;;/periodical;;pages;262-265;/pages;;volume;69;/volume;;number;822;/number;;dates;;year;1944;/year;;/dates;;isbn;1364-5528;/isbn;;urls;;/urls;;/record;;/Cite;;Cite;;Author;Aldridge;/Author;;Year;1945;/Year;;RecNum;69;/RecNum;;record;;rec-number;69;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1524914079″;69;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Aldridge, WN;/author;;/authors;;/contributors;;titles;;title;The estimation of micro quantities of cyanide and thiocyanate;/title;;secondary-title;The Analyst;/secondary-title;;/titles;;periodical;;full-title;The Analyst;/full-title;;/periodical;;pages;474-474;/pages;;volume;70;/volume;;dates;;year;1945;/year;;/dates;;isbn;0003-2654;/isbn;;urls;;/urls;;/record;;/Cite;;/EndNote;(Aldridge, 1944, Aldridge, 1945), and by Epstein in 1947. Various modified K?nig reactions have been reported, but the core technology is similar (Figure1) ADDIN EN.CITE ;EndNote;;Cite;;Author;Mak;/Author;;Year;2005;/Year;;RecNum;18;/RecNum;;DisplayText;(Mak et al., 2005);/DisplayText;;record;;rec-number;18;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523431621″;18;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Mak, Karen K. W.;/author;;author;Yanase, Hideshi;/author;;author;Renneberg, Reinhard;/author;;/authors;;/contributors;;titles;;title;Cyanide fishing and cyanide detection in coral reef fish using chemical tests and biosensors;/title;;secondary-title;Biosensors and Bioelectronics;/secondary-title;;/titles;;periodical;;full-title;Biosensors and Bioelectronics;/full-title;;/periodical;;pages;2581-2593;/pages;;volume;20;/volume;;number;12;/number;;keywords;;keyword;Biosensor;/keyword;;keyword;Coral reef fish;/keyword;;keyword;Cyanide degrading enzyme;/keyword;;keyword;Cyanide fishing;/keyword;;keyword;Optical test;/keyword;;/keywords;;dates;;year;2005;/year;;pub-dates;;date;2005/06/15/;/date;;/pub-dates;;/dates;;isbn;0956-5663;/isbn;;urls;;related-urls;;url;http://www.sciencedirect.com/science/article/pii/S0956566304004270;/url;;/related-urls;;/urls;;electronic-resource-num;https://doi.org/10.1016/j.bios.2004.09.015;/electronic-resource-num;;/record;;/Cite;;/EndNote;(Mak et al., 2005), First the cyanide is converted to cyanogen chloride (CN-Cl( typically by tosylchloramide (chloramine-T) or hypochlorite, second the CN-Cl is then reacted with pyridine and another molecule, exemplarily barbituric acid or pyrzolone to produce coloured product (spectrophotometrically active product) PEVuZE5vdGU+PENpdGU+PEF1dGhvcj5FcHN0ZWluPC9BdXRob3I+PFllYXI+MTk0NzwvWWVhcj48
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ADDIN EN.CITE.DATA (Epstein, 1947, Baar, 1966, Nagashima, 1984, Nagashima and Ozawa, 1981, Lundquist et al., 1987, Lundquist and Sörbo, 1989, Dirikolu et al., 2003). Since thiocyanate interferes with the K?nig reaction by reacting with chloramine-T, it must be removed from the sample predated to the addition of chloramine-T ADDIN EN.CITE ;EndNote;;Cite;;Author;Jackson;/Author;;Year;2017;/Year;;RecNum;6;/RecNum;;DisplayText;(Jackson and Logue, 2017);/DisplayText;;record;;rec-number;6;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523425835″;6;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Jackson, Randy;/author;;author;Logue, Brian A.;/author;;/authors;;/contributors;;titles;;title;A review of rapid and field-portable analytical techniques for the diagnosis of cyanide exposure;/title;;secondary-title;Analytica Chimica Acta;/secondary-title;;/titles;;periodical;;full-title;Analytica Chimica Acta;/full-title;;/periodical;;pages;18-39;/pages;;volume;960;/volume;;keywords;;keyword;Cyanide detection;/keyword;;keyword;Sensor;/keyword;;keyword;Cyanide poisoning diagnosis;/keyword;;keyword;Bioanalysis;/keyword;;/keywords;;dates;;year;2017;/year;;pub-dates;;date;2017/04/01/;/date;;/pub-dates;;/dates;;isbn;0003-2670;/isbn;;urls;;related-urls;;url;http://www.sciencedirect.com/science/article/pii/S0003267016315148;/url;;/related-urls;;/urls;;electronic-resource-num;https://doi.org/10.1016/j.aca.2016.12.039;/electronic-resource-num;;/record;;/Cite;;/EndNote;(Jackson and Logue, 2017). Spectrophotometric methods based K?nig synthesis is the most commonly method used For the detection of small amounts of ionic cyanide, thiocyanate by reaction of cyanogen bromide or chloride with pyridine and an aromatic amine to form a dye than other method. Also method measures most nicotine metabolites, including cotinine and 3-hydroxy-cotinine, which were shown to be the major metabolites of nicotine in human urine ADDIN EN.CITE ;EndNote;;Cite;;Author;Pickert;/Author;;Year;1993;/Year;;RecNum;2;/RecNum;;DisplayText;(Pickert et al., 1993);/DisplayText;;record;;rec-number;2;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523424143″;2;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Pickert, Andreas;/author;;author;Lingenfelser, Thomas;/author;;author;Pickert, Christiane;/author;;author;Birbaumer, Niels;/author;;author;Overkamp, Dietrich;/author;;author;Eggstein, Manfred;/author;;/authors;;/contributors;;titles;;title;Comparison of a mechanized version of the ‘König’ reaction and a fluorescence polarization immunoassay for the determination of nicotine metabolites in urine;/title;;secondary-title;Clinica Chimica Acta;/secondary-title;;/titles;;periodical;;full-title;Clinica Chimica Acta;/full-title;;/periodical;;pages;143-152;/pages;;volume;217;/volume;;number;2;/number;;keywords;;keyword;Smoking;/keyword;;keyword;Cotinine determination;/keyword;;keyword;’König’ reaction;/keyword;;keyword;Fluorescence polarization immunoassay;/keyword;;keyword;Automated analysis;/keyword;;/keywords;;dates;;year;1993;/year;;pub-dates;;date;1993/08/31/;/date;;/pub-dates;;/dates;;isbn;0009-8981;/isbn;;urls;;related-urls;;url;http://www.sciencedirect.com/science/article/pii/0009898193901606;/url;;/related-urls;;/urls;;electronic-resource-num;https://doi.org/10.1016/0009-8981(93)90160-6;/electronic-resource-num;;/record;;/Cite;;/EndNote;(Pickert et al., 1993).One of the major cyanide sources in daily human activity is the inhaled smoke by cigarette smokers, causing increased thiocyanate ion levels in human fluid which is the main product of the metabolism of cyanides. Although the toxicity of thiocyanate is significantly less than that of cyanide, chronically elevated levels of thiocyanate can block the uptake of iodine by the thyroid gland, thereby lowering the formation of thyroxine ADDIN EN.CITE ;EndNote;;Cite;;Author;Themelis;/Author;;Year;2002;/Year;;RecNum;58;/RecNum;;DisplayText;(Themelis and Tzanavaras, 2002);/DisplayText;;record;;rec-number;58;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1524380059″;58;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Themelis, Demetrius G.;/author;;author;Tzanavaras, Paraskevas D.;/author;;/authors;;/contributors;;titles;;title;Solvent extraction flow-injection manifold for the simultaneous spectrophotometric determination of free cyanide and thiocyanate ions based upon on-line masking of cyanides by formaldehyde;/title;;secondary-title;Analytica Chimica Acta;/secondary-title;;/titles;;periodical;;full-title;Analytica Chimica Acta;/full-title;;/periodical;;pages;295-302;/pages;;volume;452;/volume;;number;2;/number;;keywords;;keyword;Solvent extraction;/keyword;;keyword;Flow-injection spectrophotometry;/keyword;;keyword;Cyanide;/keyword;;keyword;Thiocyanate;/keyword;;keyword;Simultaneous determination;/keyword;;keyword;Human saliva;/keyword;;keyword;Pralidoxime;/keyword;;/keywords;;dates;;year;2002;/year;;pub-dates;;date;2002/02/11/;/date;;/pub-dates;;/dates;;isbn;0003-2670;/isbn;;urls;;related-urls;;url;http://www.sciencedirect.com/science/article/pii/S0003267001012260;/url;;/related-urls;;/urls;;electronic-resource-num;https://doi.org/10.1016/S0003-2670(01)01226-0;/electronic-resource-num;;/record;;/Cite;;/EndNote;(Themelis and Tzanavaras, 2002). The aim of this article is to show the enormous number of analytical method to the determination of cyanide, thiocyanid and nicotinic compound.

Figure 1: The chemistry of the colorimetry determination of cyanide. Cyanide is converted to cyanogen chloride (ClCN) by chloramine-T. ClCN is then reacted with pyridine to formN-cyanopyridinium chloride (K?nig reaction), which undergoes hydrolysis to glutaconic aldehyde, the aldehyde is couple with barbituric acid to form a colored product.

2. Cyanide
The cyanide ion consists of a carbon atom triply bonded to a nitrogen atom; it is a highly toxic chemical that is used in many industries, because it ability to complex to a range of metals has been utilized in several industrial processes including mining for the extraction of ores, metallurgy, electroplating , photo graphic industry and in the production of organic chemicals such pesticide production ADDIN EN.CITE ;EndNote;;Cite;;Author;Noroozifar;/Author;;Year;2005;/Year;;RecNum;65;/RecNum;;DisplayText;(Noroozifar et al., 2005);/DisplayText;;record;;rec-number;65;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1524903035″;65;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Noroozifar, M.;/author;;author;Khorasani-Motlagh, M.;/author;;author;Hosseini, S. N.;/author;;/authors;;/contributors;;titles;;title;Flow injection analysis–flame atomic absorption spectrometry system for indirect determination of cyanide using cadmium carbonate as a new solid-phase reactor;/title;;secondary-title;Analytica Chimica Acta;/secondary-title;;/titles;;periodical;;full-title;Analytica Chimica Acta;/full-title;;/periodical;;pages;269-273;/pages;;volume;528;/volume;;number;2;/number;;keywords;;keyword;Indirect determination;/keyword;;keyword;Cyanide;/keyword;;keyword;Cadmium carbonate;/keyword;;keyword;Flow injection analysis;/keyword;;keyword;Flame atomic absorption spectrometry;/keyword;;/keywords;;dates;;year;2005;/year;;pub-dates;;date;2005/01/10/;/date;;/pub-dates;;/dates;;isbn;0003-2670;/isbn;;urls;;related-urls;;url;http://www.sciencedirect.com/science/article/pii/S0003267004014096;/url;;/related-urls;;/urls;;electronic-resource-num;https://doi.org/10.1016/j.aca.2004.10.056;/electronic-resource-num;;/record;;/Cite;;/EndNote;(Noroozifar et al., 2005). May be released into the aquatic environment through waste flowed from numerouse industries and processes ADDIN EN.CITE ;EndNote;;Cite;;Author;Kang;/Author;;Year;2014;/Year;;RecNum;40;/RecNum;;DisplayText;(Kang and Shin, 2014);/DisplayText;;record;;rec-number;40;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523602091″;40;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Kang, Hye-In;/author;;author;Shin, Ho-Sang;/author;;/authors;;/contributors;;titles;;title;Ultra-sensitive determination of cyanide in surface water by gas chromatography–tandem mass spectrometry after derivatization with 2-(dimethylamino) ethanethiol;/title;;secondary-title;Analytica chimica acta;/secondary-title;;/titles;;periodical;;full-title;Analytica Chimica Acta;/full-title;;/periodical;;pages;168-173;/pages;;volume;852;/volume;;dates;;year;2014;/year;;/dates;;isbn;0003-2670;/isbn;;urls;;/urls;;/record;;/Cite;;/EndNote;(Kang and Shin, 2014). Also many substances are potential sources of cyanide exposure, including edible and non-edible plants (e.g., cassava), industrial operations (e.g., plastics processing), fires, and cigarette smoke. The primary natural source of cyanide poisoning is from plants, other natural sources include volcanoes, bacteria, and fungi ADDIN EN.CITE ;EndNote;;Cite;;Author;Logue;/Author;;Year;2010;/Year;;RecNum;13;/RecNum;;DisplayText;(Logue et al., 2010);/DisplayText;;record;;rec-number;13;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523430358″;13;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Logue, Brian A;/author;;author;Hinkens, Diane M;/author;;author;Baskin, Steven I;/author;;author;Rockwood, Gary A;/author;;/authors;;/contributors;;titles;;title;The analysis of cyanide and its breakdown products in biological samples;/title;;secondary-title;Critical Reviews in Analytical Chemistry;/secondary-title;;/titles;;periodical;;full-title;Critical Reviews in Analytical Chemistry;/full-title;;/periodical;;pages;122-147;/pages;;volume;40;/volume;;number;2;/number;;dates;;year;2010;/year;;/dates;;isbn;1040-8347;/isbn;;urls;;/urls;;/record;;/Cite;;/EndNote;(Logue et al., 2010). Although there are other chemical forms of cyanide (e.g. cyanide ion), it is Hydrogen cyanide (HCN) vapor is extremely dangerous to human beings and animals as it inhibits the consumption of oxygen by body tissues ADDIN EN.CITE ;EndNote;;Cite;;Author;Yang;/Author;;Year;2011;/Year;;RecNum;32;/RecNum;;DisplayText;(Yang et al., 2011);/DisplayText;;record;;rec-number;32;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523462991″;32;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Yang, Mingqing;/author;;author;He, Junhui;/author;;author;Hu, Xiaochun;/author;;author;Yan, Chunxiao;/author;;author;Cheng, Zhenxing;/author;;author;Zhao, Yingqiang;/author;;author;Zuo, Guomin;/author;;/authors;;/contributors;;titles;;title;Copper oxide nanoparticle sensors for hydrogen cyanide detection: Unprecedented selectivity and sensitivity;/title;;secondary-title;Sensors and Actuators B: Chemical;/secondary-title;;/titles;;periodical;;full-title;Sensors and Actuators B: Chemical;/full-title;;/periodical;;pages;692-698;/pages;;volume;155;/volume;;number;2;/number;;keywords;;keyword;Copper oxide;/keyword;;keyword;Quartz crystal microbalance;/keyword;;keyword;Gas sensor;/keyword;;keyword;Hydrogen cyanide;/keyword;;/keywords;;dates;;year;2011;/year;;pub-dates;;date;2011/07/20/;/date;;/pub-dates;;/dates;;isbn;0925-4005;/isbn;;urls;;related-urls;;url;http://www.sciencedirect.com/science/article/pii/S0925400511000487;/url;;/related-urls;;/urls;;electronic-resource-num;https://doi.org/10.1016/j.snb.2011.01.031;/electronic-resource-num;;/record;;/Cite;;/EndNote;(Yang et al., 2011). The heart and brain are particularly susceptible to the harmful effects of HCN, as they are organs with high rates of aerobic metabolism ADDIN EN.CITE ;EndNote;;Cite;;Author;Porter;/Author;;Year;2007;/Year;;RecNum;31;/RecNum;;DisplayText;(Porter et al., 2007);/DisplayText;;record;;rec-number;31;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523462786″;31;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Porter, Timothy L.;/author;;author;Vail, Timothy L.;/author;;author;Eastman, Michael P.;/author;;author;Stewart, Ray;/author;;author;Reed, Jim;/author;;author;Venedam, Richard;/author;;author;Delinger, William;/author;;/authors;;/contributors;;titles;;title;A solid-state sensor platform for the detection of hydrogen cyanide gas;/title;;secondary-title;Sensors and Actuators B: Chemical;/secondary-title;;/titles;;periodical;;full-title;Sensors and Actuators B: Chemical;/full-title;;/periodical;;pages;313-317;/pages;;volume;123;/volume;;number;1;/number;;keywords;;keyword;Piezoresistive;/keyword;;keyword;Microcantilever;/keyword;;keyword;Cyanide;/keyword;;keyword;Embedded;/keyword;;/keywords;;dates;;year;2007;/year;;pub-dates;;date;2007/04/10/;/date;;/pub-dates;;/dates;;isbn;0925-4005;/isbn;;urls;;related-urls;;url;http://www.sciencedirect.com/science/article/pii/S0925400506005727;/url;;/related-urls;;/urls;;electronic-resource-num;https://doi.org/10.1016/j.snb.2006.08.025;/electronic-resource-num;;/record;;/Cite;;/EndNote;(Porter et al., 2007). There toxicity is caused by its affinity to iron in the mitochondrial cytochrome C, and blocks the end stage of electron transport chain which results in cellular hypoxia and changes leading to ATP depletion, metabolic acidosis and consequently to cellular death ADDIN EN.CITE ;EndNote;;Cite;;Author;Narkowicz;/Author;;Year;2013;/Year;;RecNum;54;/RecNum;;DisplayText;(Narkowicz et al., 2013);/DisplayText;;record;;rec-number;54;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523908017″;54;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Narkowicz, Sylwia;/author;;author;Polkowska, ?aneta;/author;;author;Namie?nik, Jacek;/author;;/authors;;/contributors;;titles;;title;Determination of formaldehyde and cyanide ion in human nasal discharge by using simple spectrophotometric methods;/title;;secondary-title;Open Chemistry;/secondary-title;;/titles;;periodical;;full-title;Open Chemistry;/full-title;;/periodical;;pages;16-24;/pages;;volume;11;/volume;;number;1;/number;;dates;;year;2013;/year;;/dates;;isbn;2391-5420;/isbn;;urls;;/urls;;/record;;/Cite;;/EndNote;(Narkowicz et al., 2013). The extreme toxicity of cyanide in physiological systems, as well as the continuing environmental concern caused by its widespread industrial use, has led to extensive research into the development of cyanide detection methods ADDIN EN.CITE ;EndNote;;Cite;;Author;Surleva;/Author;;Year;2016;/Year;;RecNum;39;/RecNum;;DisplayText;(Surleva et al., 2016);/DisplayText;;record;;rec-number;39;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523601865″;39;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Surleva, Andriana;/author;;author;Zaharia, Marius;/author;;author;Pintilie, Olga;/author;;author;Sandu, Ion;/author;;author;Tudorachi, Lucia;/author;;author;Gradinaru, Robert Vasile;/author;;/authors;;/contributors;;titles;;title;Improved ninhydrin-based reagent for spectrophotometric determination of ppb levels of cyanide;/title;;secondary-title;Environmental Forensics;/secondary-title;;/titles;;periodical;;full-title;Environmental Forensics;/full-title;;/periodical;;pages;48-58;/pages;;volume;17;/volume;;number;1;/number;;dates;;year;2016;/year;;/dates;;isbn;1527-5922;/isbn;;urls;;/urls;;/record;;/Cite;;/EndNote;(Surleva et al., 2016). The majority of the population is exposed to very low levels of cyanide in the general environment ADDIN EN.CITE ;EndNote;;Cite;;Author;Surleva;/Author;;Year;2012;/Year;;RecNum;51;/RecNum;;DisplayText;(Surleva et al., 2012);/DisplayText;;record;;rec-number;51;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523781022″;51;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Surleva, Andriana;/author;;author;Gradinaru, Robert;/author;;author;Drochioiu, Gabi;/author;;/authors;;/contributors;;titles;;title;Cyanide poisoning: from physiology to forensic analytical chemistry;/title;;secondary-title;Int. J. Crim. Invest;/secondary-title;;/titles;;periodical;;full-title;Int. J. Crim. Invest;/full-title;;/periodical;;pages;79;/pages;;volume;2;/volume;;dates;;year;2012;/year;;/dates;;urls;;/urls;;/record;;/Cite;;/EndNote;(Surleva et al., 2012). Once absorbed, cyanide is quickly transferred to the blood and metabolized by a number of processes (Figure 2) ADDIN EN.CITE ;EndNote;;Cite;;Author;Egekeze;/Author;;Year;1980;/Year;;RecNum;30;/RecNum;;DisplayText;(Egekeze and Oehme, 1980);/DisplayText;;record;;rec-number;30;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523457201″;30;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Egekeze, John O;/author;;author;Oehme, Frederick W;/author;;/authors;;/contributors;;titles;;title;Cyanides and their toxicity: a literature review;/title;;secondary-title;Veterinary Quarterly;/secondary-title;;/titles;;periodical;;full-title;Veterinary Quarterly;/full-title;;/periodical;;pages;104-114;/pages;;volume;2;/volume;;number;2;/number;;dates;;year;1980;/year;;/dates;;isbn;0165-2176;/isbn;;urls;;/urls;;/record;;/Cite;;/EndNote;(Egekeze and Oehme, 1980). The analysis of biological matrices, specifically urine and blood, to verify exposure to cyanide is important to determine past exposure to cyanide. Due to its volatility hydrogen cyanide rapidly dissipates from open areas ADDIN EN.CITE ;EndNote;;Cite;;Author;Logue;/Author;;Year;2005;/Year;;RecNum;64;/RecNum;;DisplayText;(Logue et al., 2005);/DisplayText;;record;;rec-number;64;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1524902474″;64;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Logue, Brian A.;/author;;author;Kirschten, Nicholas P.;/author;;author;Petrikovics, Ilona;/author;;author;Moser, Matthew A.;/author;;author;Rockwood, Gary A.;/author;;author;Baskin, Steven I.;/author;;/authors;;/contributors;;titles;;title;Determination of the cyanide metabolite 2-aminothiazoline-4-carboxylic acid in urine and plasma by gas chromatography–mass spectrometry;/title;;secondary-title;Journal of Chromatography B;/secondary-title;;/titles;;periodical;;full-title;Journal of Chromatography B;/full-title;;/periodical;;pages;237-244;/pages;;volume;819;/volume;;number;2;/number;;keywords;;keyword;Cyanide;/keyword;;keyword;2-Aminothiazoline-4-carboxylic acid;/keyword;;keyword;GC–MS;/keyword;;keyword;Chemical warfare agent;/keyword;;/keywords;;dates;;year;2005;/year;;pub-dates;;date;2005/05/25/;/date;;/pub-dates;;/dates;;isbn;1570-0232;/isbn;;urls;;related-urls;;url;http://www.sciencedirect.com/science/article/pii/S1570023205001947;/url;;/related-urls;;/urls;;electronic-resource-num;https://doi.org/10.1016/j.jchromb.2005.01.045;/electronic-resource-num;;/record;;/Cite;;/EndNote;(Logue et al., 2005). The analysis of cyanide in biological fluids is of attentions because cyanide acts not only as an acute toxicant, which binds to and inhibits the activity of cytochrome oxidase, but also as a chronic toxicant ADDIN EN.CITE ;EndNote;;Cite;;Author;Chinaka;/Author;;Year;1998;/Year;;RecNum;7;/RecNum;;DisplayText;(Chinaka et al., 1998);/DisplayText;;record;;rec-number;7;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523428920″;7;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Chinaka, Satoshi;/author;;author;Takayama, Nariaki;/author;;author;Michigami, Yoshimasa;/author;;author;Ueda, Kazumasa;/author;;/authors;;/contributors;;titles;;title;Simultaneous determination of cyanide and thiocyanate in blood by ion chromatography with fluorescence and ultraviolet detection;/title;;secondary-title;Journal of Chromatography B: Biomedical Sciences and Applications;/secondary-title;;/titles;;periodical;;full-title;Journal of Chromatography B: Biomedical Sciences and Applications;/full-title;;/periodical;;pages;353-359;/pages;;volume;713;/volume;;number;2;/number;;keywords;;keyword;Cyanide;/keyword;;keyword;Thiocyanate;/keyword;;/keywords;;dates;;year;1998;/year;;pub-dates;;date;1998/08/25/;/date;;/pub-dates;;/dates;;isbn;0378-4347;/isbn;;urls;;related-urls;;url;http://www.sciencedirect.com/science/article/pii/S0378434798001765;/url;;/related-urls;;/urls;;electronic-resource-num;https://doi.org/10.1016/S0378-4347(98)00176-5;/electronic-resource-num;;/record;;/Cite;;/EndNote;(Chinaka et al., 1998). While the majority of absorbed cyanide is excreted in the urine as thiocyanate, small amounts of free cyanide may also be excreted by the lungs, sweat and saliva. Plasma half-life of 20 min to 1 hour has been estimated for cyanides in humans ADDIN EN.CITE ;EndNote;;Cite;;Author;Pritchard;/Author;;Year;2007;/Year;;RecNum;50;/RecNum;;DisplayText;(Pritchard, 2007);/DisplayText;;record;;rec-number;50;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523720325″;50;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Pritchard, JD;/author;;/authors;;/contributors;;titles;;title;Hydrogen cyanide toxicological overview;/title;;secondary-title;Health Protection Agency, CHAPD HQ;/secondary-title;;/titles;;periodical;;full-title;Health Protection Agency, CHAPD HQ;/full-title;;/periodical;;dates;;year;2007;/year;;/dates;;urls;;/urls;;/record;;/Cite;;/EndNote;(Pritchard, 2007) .

Figure 2: The fundamental processes including in the metabolism of cyanide and treatment of cyanide poisoning.

3. Thiocyanate
Thiocyanate is an important metabolic product of hydrogen cyanide which is generated by tobacco pyrolysis, the hydrogen cyanide being converted by the enzyme thiosulfate transferase (rhodanese) mainly in liver mitochondria ADDIN EN.CITE ;EndNote;;Cite;;Author;Pre;/Author;;Year;1991;/Year;;RecNum;57;/RecNum;;DisplayText;(Pre and Vassy, 1991);/DisplayText;;record;;rec-number;57;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1524379829″;57;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Pre, Jacques;/author;;author;Vassy, Roger;/author;;/authors;;/contributors;;titles;;title;Urine thiocyanate: creatinine ratio as a reliable indicator of cigarette smoking;/title;;secondary-title;Clinica chimica acta;/secondary-title;;/titles;;periodical;;full-title;Clinica Chimica Acta;/full-title;;/periodical;;pages;87-94;/pages;;volume;204;/volume;;number;1-3;/number;;dates;;year;1991;/year;;/dates;;isbn;0009-8981;/isbn;;urls;;/urls;;/record;;/Cite;;/EndNote;(Pre and Vassy, 1991). usually it present in low concentrations in human serum, urine and saliva as a result of the digestion of some vegetables containing glucosinolates such as (cabbage) or by intake of thiocyanate containing foods such as milk, and Higher concentration of this ion, which is a metabolic product of cyanide, arises from tobacco smoke ADDIN EN.CITE ;EndNote;;Cite;;Author;Glatz;/Author;;Year;2001;/Year;;RecNum;14;/RecNum;;DisplayText;(Glatz et al., 2001);/DisplayText;;record;;rec-number;14;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523430522″;14;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Glatz, Zden?k;/author;;author;Nováková, So?a;/author;;author;Št?rbová, Hana;/author;;/authors;;/contributors;;titles;;title;Analysis of thiocyanate in biological fluids by capillary zone electrophoresis;/title;;secondary-title;Journal of Chromatography A;/secondary-title;;/titles;;periodical;;full-title;Journal of Chromatography A;/full-title;;/periodical;;pages;273-277;/pages;;volume;916;/volume;;number;1;/number;;keywords;;keyword;Thiocyanate;/keyword;;keyword;Inorganic anions;/keyword;;/keywords;;dates;;year;2001;/year;;pub-dates;;date;2001/05/04/;/date;;/pub-dates;;/dates;;isbn;0021-9673;/isbn;;urls;;related-urls;;url;http://www.sciencedirect.com/science/article/pii/S0021967300012383;/url;;/related-urls;;/urls;;electronic-resource-num;https://doi.org/10.1016/S0021-9673(00)01238-3;/electronic-resource-num;;/record;;/Cite;;/EndNote;(Glatz et al., 2001). But it presence in the body fluids cannot be ruled out clinically, since a large dose of thiocyanate as a hypotensive agent caused cyanide poisoning. Therefore, an accurate and reliable method for the determination of thiocyanate in biological sample is desired ADDIN EN.CITE ;EndNote;;Cite;;Author;Ensafi;/Author;;Year;1995;/Year;;RecNum;59;/RecNum;;DisplayText;(Ensafi and Tajebakhsh-E-Ardakany, 1995);/DisplayText;;record;;rec-number;59;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1524398349″;59;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Ensafi, Ali A;/author;;author;Tajebakhsh-E-Ardakany, J;/author;;/authors;;/contributors;;titles;;title;Determination of thiocyanate at the nanogram level by a kinetic method;/title;;secondary-title;Analytical letters;/secondary-title;;/titles;;periodical;;full-title;Analytical letters;/full-title;;/periodical;;pages;731-747;/pages;;volume;28;/volume;;number;4;/number;;dates;;year;1995;/year;;/dates;;isbn;0003-2719;/isbn;;urls;;/urls;;/record;;/Cite;;/EndNote;(Ensafi and Tajebakhsh-E-Ardakany, 1995). And there concentration in body fluid is considered to be a good indicator for drug monitoring in patients treated with cyano-containing drug such as sodium nitroprusside, the blood concentrations of SCN- can also be used for differentiating between smoker and nonsmoker ADDIN EN.CITE ;EndNote;;Cite;;Author;Chen;/Author;;Year;1996;/Year;;RecNum;11;/RecNum;;DisplayText;(Chen et al., 1996);/DisplayText;;record;;rec-number;11;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523429828″;11;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Chen, Su-Hwei;/author;;author;Yang, Zi-Yuan;/author;;author;Wu, Hsin-Lung;/author;;author;Kou, Hwang-Shang;/author;;author;Lin, Shun-Jin;/author;;/authors;;/contributors;;titles;;title;Determination of thiocyanate anion by high-performance liquid chromatography with fluorimetric detection;/title;;secondary-title;Journal of analytical toxicology;/secondary-title;;/titles;;periodical;;full-title;Journal of analytical toxicology;/full-title;;/periodical;;pages;38-42;/pages;;volume;20;/volume;;number;1;/number;;dates;;year;1996;/year;;/dates;;isbn;1945-2403;/isbn;;urls;;/urls;;/record;;/Cite;;/EndNote;(Chen et al., 1996). Thiocyanate (SCN-) as a negative ion is present in industrial wastewater, environmental water and organism metabolites .The major thiocyanate pollution is generated by the reaction of free cyanide with sulfur during the coal conversion (e.g gasification, refining, coking and liquefaction) and the metallurgical process ADDIN EN.CITE ;EndNote;;Cite;;Author;Jafari;/Author;;Year;2010;/Year;;RecNum;23;/RecNum;;DisplayText;(Jafari and Javaheri, 2010);/DisplayText;;record;;rec-number;23;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523434752″;23;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Jafari, MT;/author;;author;Javaheri, M;/author;;/authors;;/contributors;;titles;;title;Selective method based on negative electrospray ionization ion mobility spectrometry for direct analysis of salivary thiocyanate;/title;;secondary-title;Analytical chemistry;/secondary-title;;/titles;;periodical;;full-title;Analytical Chemistry;/full-title;;/periodical;;pages;6721-6725;/pages;;volume;82;/volume;;number;15;/number;;dates;;year;2010;/year;;/dates;;isbn;0003-2700;/isbn;;urls;;/urls;;/record;;/Cite;;/EndNote;(Jafari and Javaheri, 2010).
4. Analytical method based on k?nig reaction
Several methods have been reported for the detection of cyanide, thiocyanate and nicotinic acid based on the K?nig reaction. A spectrophotometry method is most available which is developed by Aldridge and Epstein have been most often used. Both of these methods are based on the K?nig reaction for the synthesis of pyridine dyestuffs. Bark and Hajson PEVuZE5vdGU+PENpdGU+PEF1dGhvcj5CYXJrPC9BdXRob3I+PFllYXI+MTk2NDwvWWVhcj48UmVj
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ADDIN EN.CITE.DATA (Bark and Higson, 1964a, Bark and Higson, 1964b) have shown that other heterocyclic amines are unsuitable as a replacement for pyridine, while p-phenylenediamine is the amine of choice for use in the color reagent. However, the greater disadvantages in the use of amines in the color reagent, has been their dangerous physiological properties. The carcinogenic properties of benzidine are well known. Dianisidine and the tolidines are suspected of being carcinogenic while p-phenylenediamine is an allergen. The greatest drawback of the Epstein procedure is the relatively unstable color reagent which has to be prepared fresh immediately before use. The use of barbituric acid has numerous disadvantages associated with the color reagent, such as. the use of a large sample size, the instability of the reagent, and also of the color formed ADDIN EN.CITE ;EndNote;;Cite;;Author;Sharma;/Author;;Year;1985;/Year;;RecNum;46;/RecNum;;DisplayText;(Sharma and Thibert, 1985);/DisplayText;;record;;rec-number;46;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523603743″;46;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Sharma, A;/author;;author;Thibert, RJ;/author;;/authors;;/contributors;;titles;;title;The effect of barbituric acid concentration in the spectrophotometric determination of cyanide and thiocyanate by the pyridine-barbituric acid method;/title;;secondary-title;Microchimica Acta;/secondary-title;;/titles;;periodical;;full-title;Microchimica Acta;/full-title;;/periodical;;pages;357-363;/pages;;volume;85;/volume;;number;5-6;/number;;dates;;year;1985;/year;;/dates;;isbn;0026-3672;/isbn;;urls;;/urls;;/record;;/Cite;;/EndNote;(Sharma and Thibert, 1985). Most of these method spectrophotometric based on k?nig reaction PEVuZE5vdGU+PENpdGU+PEF1dGhvcj5QZXR0aWdyZXc8L0F1dGhvcj48WWVhcj4xOTcyPC9ZZWFy
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ADDIN EN.CITE.DATA (Pettigrew and Fell, 1972, Lundquist et al., 1979, Tsuge et al., 2000, Nagashima, 1984, Nagashima, 1983, ADDIN EN.CITE ;EndNote;;Cite;;Author;Casassas;/Author;;Year;1989;/Year;;RecNum;43;/RecNum;;DisplayText;(Casassas et al., 1989);/DisplayText;;record;;rec-number;43;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523603341″;43;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Casassas, E;/author;;author;Peydro, M;/author;;author;Puignou, L;/author;;/authors;;/contributors;;titles;;title;Kinetic Spectrophotometric Determination of Trace Amounts of Pyridine With 4, 4?-Diaminostilbene-2, 2?-Disulphonic Acid;/title;;secondary-title;Analytical letters;/secondary-title;;/titles;;periodical;;full-title;Analytical letters;/full-title;;/periodical;;pages;729-740;/pages;;volume;22;/volume;;number;3;/number;;dates;;year;1989;/year;;/dates;;isbn;0003-2719;/isbn;;urls;;/urls;;/record;;/Cite;;/EndNote;Casassas et al., 1989). High-performance liquid chromatography (HPLC) with fluorescence detection using a modified K?nig reaction ADDIN EN.CITE ;EndNote;;Cite;;Author;Toida;/Author;;Year;1984;/Year;;RecNum;37;/RecNum;;DisplayText;(Toida et al., 1984);/DisplayText;;record;;rec-number;37;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523601293″;37;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Toida, Toshihiko;/author;;author;Togawa, Tadayasu;/author;;author;Tanabe, Shinzo;/author;;author;Imanari, Toshio;/author;;/authors;;/contributors;;titles;;title;Determination of cyanide and thiocyanate in blood plasma and red cells by high-performance liquid chromatography with fluorometric detection;/title;;secondary-title;Journal of Chromatography B: Biomedical Sciences and Applications;/secondary-title;;/titles;;periodical;;full-title;Journal of Chromatography B: Biomedical Sciences and Applications;/full-title;;/periodical;;pages;133-141;/pages;;volume;308;/volume;;dates;;year;1984;/year;;pub-dates;;date;1984/06/08/;/date;;/pub-dates;;/dates;;isbn;0378-4347;/isbn;;urls;;related-urls;;url;http://www.sciencedirect.com/science/article/pii/0378434784802030;/url;;/related-urls;;/urls;;electronic-resource-num;https://doi.org/10.1016/0378-4347(84)80203-0;/electronic-resource-num;;/record;;/Cite;;/EndNote;(Toida et al., 1984 , ADDIN EN.CITE ;EndNote;;Cite;;Author;SHIMOKOBE;/Author;;Year;1988;/Year;;RecNum;48;/RecNum;;DisplayText;(SHIMOKOBE et al., 1988);/DisplayText;;record;;rec-number;48;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523604310″;48;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;SHIMOKOBE, Takashi;/author;;author;WATANABE, Toshinori;/author;;author;TOGAWA, Tadayasu;/author;;author;IMANARI, Toshio;/author;;/authors;;/contributors;;titles;;title;Determination of thiocyano group in biological materials;/title;;secondary-title;Analytical sciences;/secondary-title;;/titles;;periodical;;full-title;Analytical sciences;/full-title;;/periodical;;pages;97-100;/pages;;volume;4;/volume;;number;1;/number;;dates;;year;1988;/year;;/dates;;isbn;0910-6340;/isbn;;urls;;/urls;;/record;;/Cite;;/EndNote;SHIMOKOBE et al., 1988). High-performance liquid chromatography) HPLC) and colorimetric detection by the k?nig reaction ADDIN EN.CITE ;EndNote;;Cite;;Author;IMANARI;/Author;;Year;1982;/Year;;RecNum;88;/RecNum;;DisplayText;(IMANARI et al., 1982);/DisplayText;;record;;rec-number;88;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1525079591″;88;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;IMANARI, TOSHIO;/author;;author;TANABE, SHINZO;/author;;author;TOIDA, TOSHIHIKO;/author;;/authors;;/contributors;;titles;;title;Simultaneous determination of cyanide and thiocyanate by high performance liquid chromatography;/title;;secondary-title;Chemical and Pharmaceutical Bulletin;/secondary-title;;/titles;;periodical;;full-title;Chemical and Pharmaceutical Bulletin;/full-title;;/periodical;;pages;3800-3802;/pages;;volume;30;/volume;;number;10;/number;;dates;;year;1982;/year;;/dates;;isbn;0009-2363;/isbn;;urls;;/urls;;/record;;/Cite;;/EndNote;(IMANARI et al., 1982) . Fluormetric determination based on K?nig reaction ADDIN EN.CITE ;EndNote;;Cite;;Author;TOIDA;/Author;;Year;1981;/Year;;RecNum;3;/RecNum;;DisplayText;(TOIDA et al., 1981);/DisplayText;;record;;rec-number;3;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523424672″;3;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;TOIDA, TOSHIHIKO;/author;;author;TANABE, SHINZO;/author;;author;IMANARI, TOSHIO;/author;;/authors;;/contributors;;titles;;title;Fluorometric Determination of Cyanide and Thiocyanate by Konig Reaction;/title;;secondary-title;Chemical and Pharmaceutical Bulletin;/secondary-title;;/titles;;periodical;;full-title;Chemical and Pharmaceutical Bulletin;/full-title;;/periodical;;pages;3763-3764;/pages;;volume;29;/volume;;number;12;/number;;dates;;year;1981;/year;;/dates;;isbn;0009-2363;/isbn;;urls;;/urls;;/record;;/Cite;;/EndNote;(TOIDA et al., 1981, ADDIN EN.CITE ;EndNote;;Cite;;Author;Tanabe;/Author;;Year;1988;/Year;;RecNum;10;/RecNum;;DisplayText;(Tanabe et al., 1988);/DisplayText;;record;;rec-number;10;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523429676″;10;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Tanabe, Shinzo;/author;;author;Kitahara, Michie;/author;;author;Nawata, Masashi;/author;;author;Kawanabe, Kouji;/author;;/authors;;/contributors;;titles;;title;Determination of oxidizable inorganic anions by high-performance liquid chromatography with fluorescence detection and application to the determination of salivary nitrite and thiocyanate and serum thiocyanate;/title;;secondary-title;Journal of Chromatography B: Biomedical Sciences and Applications;/secondary-title;;/titles;;periodical;;full-title;Journal of Chromatography B: Biomedical Sciences and Applications;/full-title;;/periodical;;pages;29-37;/pages;;volume;424;/volume;;dates;;year;1988;/year;;pub-dates;;date;1988/01/01/;/date;;/pub-dates;;/dates;;isbn;0378-4347;/isbn;;urls;;related-urls;;url;http://www.sciencedirect.com/science/article/pii/S0378434700810737;/url;;/related-urls;;/urls;;electronic-resource-num;https://doi.org/10.1016/S0378-4347(00)81073-7;/electronic-resource-num;;/record;;/Cite;;/EndNote;Tanabe et al., 1988). Flow injection ADDIN EN.CITE ;EndNote;;Cite;;Author;Vesey;/Author;;Year;1985;/Year;;RecNum;22;/RecNum;;DisplayText;(Vesey and Kirk, 1985);/DisplayText;;record;;rec-number;22;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523434342″;22;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Vesey, Cyril J;/author;;author;Kirk, CJ;/author;;/authors;;/contributors;;titles;;title;Two automated methods for measuring plasma thiocyanate compared;/title;;secondary-title;Clinical chemistry;/secondary-title;;/titles;;periodical;;full-title;Clinical chemistry;/full-title;;/periodical;;pages;270-274;/pages;;volume;31;/volume;;number;2;/number;;dates;;year;1985;/year;;/dates;;isbn;0009-9147;/isbn;;urls;;/urls;;/record;;/Cite;;/EndNote;(Vesey and Kirk, 1985) methods based on the K?nig reaction, on use of iron-chloramine- T PEVuZE5vdGU+PENpdGU+PEF1dGhvcj5HaXJhdWRpPC9BdXRob3I+PFllYXI+MTk4MTwvWWVhcj48
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ADDIN EN.CITE.DATA (Giraudi and Grillo, 1981, Tanaka et al., 1988). Despite the advantages, many of these methods require sample pretreatment and expensive equipment’s. In addition, some methods need to use toxic reagents in the measuring procedure and interference of some existing conditions may limit the application of some methods. For example, colorimetric method has been utilized for cyanide determination based on K?nig reaction but the drawback of this method is the use of hazardous chemicals such benzidine that is carcinogenic ADDIN EN.CITE <EndNote><Cite><Author>Ghanavati</Author><Year>2014</Year><RecNum>21</RecNum><DisplayText>(Ghanavati et al., 2014)</DisplayText><record><rec-number>21</rec-number><foreign-keys><key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523434059″>21</key></foreign-keys><ref-type name=”Journal Article”>17</ref-type><contributors><authors><author>Ghanavati, Mahdi</author><author>Azad, Reza Roosta</author><author>Mousavi, Seyyed Abbas</author></authors></contributors><titles><title>Amperometric inhibition biosensor for the determination of cyanide</title><secondary-title>Sensors and Actuators B: Chemical</secondary-title></titles><periodical><full-title>Sensors and Actuators B: Chemical</full-title></periodical><pages>858-864</pages><volume>190</volume><keywords><keyword>Cyanide determination</keyword><keyword>Biosensor</keyword><keyword>Inhibition</keyword><keyword>Enzyme</keyword></keywords><dates><year>2014</year><pub-dates><date>2014/01/01/</date></pub-dates></dates><isbn>0925-4005</isbn><urls><related-urls><url>http://www.sciencedirect.com/science/article/pii/S0925400513010964</url></related-urls></urls><electronic-resource-num>https://doi.org/10.1016/j.snb.2013.09.055</electronic-resource-num></record></Cite></EndNote>(Ghanavati et al., 2014).

5. Related work

5.1. Spectrophotometric method
Determination of trace amounts of cyanide and hydrogen cyanide utilizing p-aminoacetanilide in different samples (pesticide, Coke oven effluents, air samples), the method is based on conversion of cyanide to cyanogen chloride by chloramineT and cyanogen chloride produced is coupled with pyridine to form an additional product which subsequently condenses with p-aminoacetanilide to form a coloured product measurable at 485 nm, and the results confirmed by a reported method ADDIN EN.CITE <EndNote><Cite><Author>Verma</Author><Year>1996</Year><RecNum>78</RecNum><DisplayText>(Verma and Gupta, 1996)</DisplayText><record><rec-number>78</rec-number><foreign-keys><key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1524922340″>78</key></foreign-keys><ref-type name=”Journal Article”>17</ref-type><contributors><authors><author>Verma, AK</author><author>Gupta, VK</author></authors></contributors><titles><title>Spectrophotometric Determination of Cyanide and Hydrogen Cyanide Using p-Amino benzoic Acid as a New Reagent and Its Application in Steel Industries</title><secondary-title>Asian Journal of Chemistry</secondary-title></titles><periodical><full-title>Asian Journal of Chemistry</full-title></periodical><pages>613</pages><volume>8</volume><number>4</number><dates><year>1996</year></dates><isbn>0970-7077</isbn><urls></urls></record></Cite></EndNote>(Verma and Gupta, 1996) (Table 1). Although a number of spectrophotometric methods have been reported for the determination of cyanide, the most of them use bromine water which is toxic in nature, few of the reported method use benzidine and other amino like p-phenylenediamine, compounds for coupling which are carcinogenic (Table 2). all these drawbacks are removed by using chloramine-T and p-aminoacetanilide, this work was reported by ADDIN EN.CITE <EndNote><Cite><Author>Parmar</Author><Year>2010</Year><RecNum>76</RecNum><DisplayText>(Parmar et al., 2010)</DisplayText><record><rec-number>76</rec-number><foreign-keys><key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1524918351″>76</key></foreign-keys><ref-type name=”Journal Article”>17</ref-type><contributors><authors><author>Parmar, Prachi</author><author>Pillai, Ajai Kumar</author><author>Gupta, Vinay Kumar</author></authors></contributors><titles><title>Rapid spectrophotometric determination of trace amounts of cyanide and hydrogen cyanide using p-aminoacetanilide in various samples</title><secondary-title>Journal of the Korean Chemical Society</secondary-title></titles><periodical><full-title>Journal of the Korean Chemical Society</full-title></periodical><pages>165-168</pages><volume>54</volume><number>1</number><dates><year>2010</year></dates><isbn>1017-2548</isbn><urls></urls></record></Cite></EndNote>(Parmar et al., 2010).

Table 1: Result analysis of various sample
a Mean of three replicate analysis.
b Result of analysis of Plant Air.
c Results of analysis of pesticide.
d Result of analysis of coke oven effluents.

Table 2: Comparison with other spectrophotometric method
Reagents ?max Range Remark
p-aminobenzoic acid 410 0.02 – 0.2 Extractive and less sensitive
J- Acid 400 0.02 – 0.2 Less sensitive
Sulphanilic acid 460 0.5 – 3 Less sensitive, toxic Br2 water used
Anthranilic acid 400 1 – 7 Non-toxic but less sensitive
Benzidine520 0.1 – 20 Carcinogenic reagent
Ninhydrin590 0.04 – 0.24 Less sensitive
Phloroglucinol540 0.4 – 3.4 Less sensitive
Aquacyanocobyrinic acid
heptamethyl ester 580 0.04 – 1.20 Less sensitive
p-phenylene diamine515 0.005 – 100 Carcinogenic reagent
p-aminoacetanilide 485 0.016 – 0.2 More sensitive
p-aminobenzoic acid (. ADDIN EN.CITE <EndNote><Cite><Author>Verma</Author><Year>1996</Year><RecNum>78</RecNum><DisplayText>(Verma and Gupta, 1996)</DisplayText><record><rec-number>78</rec-number><foreign-keys><key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1524922340″>78</key></foreign-keys><ref-type name=”Journal Article”>17</ref-type><contributors><authors><author>Verma, AK</author><author>Gupta, VK</author></authors></contributors><titles><title>Spectrophotometric Determination of Cyanide and Hydrogen Cyanide Using p-Amino benzoic Acid as a New Reagent and Its Application in Steel Industries</title><secondary-title>Asian Journal of Chemistry</secondary-title></titles><periodical><full-title>Asian Journal of Chemistry</full-title></periodical><pages>613</pages><volume>8</volume><number>4</number><dates><year>1996</year></dates><isbn>0970-7077</isbn><urls></urls></record></Cite></EndNote>(Verma and Gupta, 1996)
anthiranilic acid ADDIN EN.CITE <EndNote><Cite><Author>Upadhyay</Author><Year>1984</Year><RecNum>79</RecNum><DisplayText>(Upadhyay and Gupta, 1984)</DisplayText><record><rec-number>79</rec-number><foreign-keys><key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1524924550″>79</key></foreign-keys><ref-type name=”Journal Article”>17</ref-type><contributors><authors><author>Upadhyay, Sweta</author><author>Gupta, VK</author></authors></contributors><titles><title>Spectrophotometric method for the determination of cyanide and its application to biological fluids</title><secondary-title>Analyst</secondary-title></titles><periodical><full-title>Analyst</full-title></periodical><pages>1619-1620</pages><volume>109</volume><number>12</number><dates><year>1984</year></dates><isbn>1364-5528</isbn><urls></urls></record></Cite></EndNote>(Upadhyay and Gupta, 1984)
ninhydrin ADDIN EN.CITE <EndNote><Cite><Author>Nagaraja</Author><Year>2002</Year><RecNum>80</RecNum><DisplayText>(Nagaraja et al., 2002)</DisplayText><record><rec-number>80</rec-number><foreign-keys><key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1524924953″>80</key></foreign-keys><ref-type name=”Journal Article”>17</ref-type><contributors><authors><author>Nagaraja, Padmarajaiah</author><author>KUMAR, Mattighatta S HEMANTHA</author><author>Yathirajan, Hemmige S</author><author>PRAKASH, Jainara S</author></authors></contributors><titles><title>Novel sensitive spectrophotometric method for the trace determination of cyanide in industrial effluent</title><secondary-title>Analytical sciences</secondary-title></titles><periodical><full-title>Analytical sciences</full-title></periodical><pages>1027-1030</pages><volume>18</volume><number>9</number><dates><year>2002</year></dates><isbn>0910-6340</isbn><urls></urls></record></Cite></EndNote>(Nagaraja et al., 2002)
p-phenylene diamine ADDIN EN.CITE <EndNote><Cite><Author>Bark</Author><Year>1964</Year><RecNum>81</RecNum><DisplayText>(Bark and Higson, 1964a)</DisplayText><record><rec-number>81</rec-number><foreign-keys><key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1524925456″>81</key></foreign-keys><ref-type name=”Journal Article”>17</ref-type><contributors><authors><author>Bark, L. S.</author><author>Higson, H. G.</author></authors></contributors><titles><title>Investigation of reagents for the colorimetric determination of small amounts of cyanide-II11Part I: see reference 4.: A proposed method for trace cyanide in waters</title><secondary-title>Talanta</secondary-title></titles><periodical><full-title>Talanta</full-title></periodical><pages>621-631</pages><volume>11</volume><number>3</number><dates><year>1964</year><pub-dates><date>1964/03/01/</date></pub-dates></dates><isbn>0039-9140</isbn><urls><related-urls><url>http://www.sciencedirect.com/science/article/pii/0039914064800734</url></related-urls></urls><electronic-resource-num>https://doi.org/10.1016/0039-9140(64)80073-4</electronic-resource-num></record></Cite></EndNote>(Bark and Higson, 1964a)
A sensitive reagent system is proposed for the detection of cyanide and hydrogen cyanide in different environmental samples, the method is based on the conversion of cyanide into cyanogen bromide followed by its reaction with pyridine to form glutaconic aldehyde, p-aminoacetophenone is added at last step, then the reaction mixture coupled with formed glutaconicaldehyde and yellow dye (polymethylene dye) showed maximum absorbanceat 445 nm (Figure 3). The method has been successfully applied for the determination of cyanide in industrial effluent, air and biological fluids and it is suitable for industrial hygiene work as well as for the determination of pesticide acrylonitrile, this work reported by ADDIN EN.CITE <EndNote><Cite><Author>Agrawal</Author><Year>2005</Year><RecNum>63</RecNum><DisplayText>(Agrawal et al., 2005)</DisplayText><record><rec-number>63</rec-number><foreign-keys><key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1524901892″>63</key></foreign-keys><ref-type name=”Journal Article”>17</ref-type><contributors><authors><author>Agrawal, Omi</author><author>Sunita, G</author><author>Gupta, VK</author></authors></contributors><titles><title>A sensitive colorimetric reagent for the determination of cyanide and hydrogen cyanide in various environmental samples</title><secondary-title>Journal of the Chinese Chemical Society</secondary-title></titles><periodical><full-title>Journal of the Chinese Chemical Society</full-title></periodical><pages>51-57</pages><volume>52</volume><number>1</number><dates><year>2005</year></dates><isbn>2192-6549</isbn><urls></urls></record></Cite></EndNote>(Agrawal et al., 2005).

Figure 3: Colour reaction of cyanide
A spectrophotometric method used for the determination of total cyanide in surface waters. Surface waters can be affected by the run-off from road salt which often contains sodium hexacyanoferrate (II) as an anti-caking agent. The method is based on the decomposition of complexes cyanide to free cyanide by exposure to short wave ultraviolet (UV) light, the sample is then analyzed for free cyanide by a method based on the K?nig reaction, the optimum sample UV irradiation time and the effect of NaCl on the spectrophotometric method were investigated (Table 3). The concentration of NaCl is used it selected to cover the concentrations of NaCl found in waters adjacent to road-salt storage facilities, were the slopes of the linear regression 3.00, 2.94, 2.90 and 2.79 A pg-1 and added NaCl 0, 1, 5 and 10g l-1, respectively, as a result concluded decrease in the slope coefficient with increasing NaCl concentrations this indicates that NaCl interferes with the spectrophotometric procedure, the method was applied to different surface water samples using standard additions to eliminate the interference from high salt concentrations and background sample colour in some surface water samples, this work reported by ADDIN EN.CITE <EndNote><Cite><Author>Ohno</Author><Year>1989</Year><RecNum>45</RecNum><DisplayText>(Ohno, 1989)</DisplayText><record><rec-number>45</rec-number><foreign-keys><key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523603583″>45</key></foreign-keys><ref-type name=”Journal Article”>17</ref-type><contributors><authors><author>Ohno, Tsutomu</author></authors></contributors><titles><title>Spectrophotometric determination of total cyanide in surface waters following ultraviolet induced photodecomposition</title><secondary-title>Analyst</secondary-title></titles><periodical><full-title>Analyst</full-title></periodical><pages>857-858</pages><volume>114</volume><number>7</number><dates><year>1989</year></dates><urls></urls></record></Cite></EndNote>(Ohno, 1989).

88392035623500Table 3: Effect of NaCI on the linear calibration equations for cyanide,when ( r ) is correlation
Hydrogen cyanide is most frequently determined in air by spectrophotometric methods based on K?nig’s reaction, which has a reasonably high sensitivity and reproducibility. Hydrogen cyanide present in air is absorbed in 0.002 M sodium hydroxide solution, which is coupled with bromin to form cyanigen bromide, and the cyanogen bromide so formed reacts with pyridine to form glutaconicaldehyde, the latter readily reacts with anthranilic acid to form a coloured polymethine dye, and shows a maximum absorbance at 400 nm, the result compared (Table 4) with the standard benzidine method given by Alridge ADDIN EN.CITE ;EndNote;;Cite;;Author;Aldridge;/Author;;Year;1944;/Year;;RecNum;55;/RecNum;;DisplayText;(Aldridge, 1944);/DisplayText;;record;;rec-number;55;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1524374700″;55;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Aldridge, W_ N;/author;;/authors;;/contributors;;titles;;title;A new method for the estimation of micro quantities of cyanide and thiocyanate;/title;;secondary-title;Analyst;/secondary-title;;/titles;;periodical;;full-title;Analyst;/full-title;;/periodical;;pages;262-265;/pages;;volume;69;/volume;;number;822;/number;;dates;;year;1944;/year;;/dates;;isbn;1364-5528;/isbn;;urls;;/urls;;/record;;/Cite;;/EndNote;(Aldridge, 1944). Also the method has been successfully applied to the determination of cyanide in biological samples such cysteine and whole blood ( Table 5), the results show 100% recovery of hydrogen cyanide from cysteine, which is in agreement with the results of the pyrazolone method ADDIN EN.CITE ;EndNote;;Cite;;Author;Johnson;/Author;;Year;1985;/Year;;RecNum;91;/RecNum;;DisplayText;(Johnson and Williams, 1985);/DisplayText;;record;;rec-number;91;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1525163347″;91;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Johnson, Deadre J;/author;;author;Williams, Harold L;/author;;/authors;;/contributors;;titles;;title;A Modified Method for Measuring Cyanide in Biological Specimens;/title;;secondary-title;Analytical Letters;/secondary-title;;/titles;;periodical;;full-title;Analytical letters;/full-title;;/periodical;;pages;855-869;/pages;;volume;18;/volume;;number;7;/number;;dates;;year;1985;/year;;/dates;;isbn;0003-2719;/isbn;;urls;;/urls;;/record;;/Cite;;/EndNote;(Johnson and Williams, 1985). The sensitivity of the method is better than reported methods, in addition rapid, simple, no made of carcinogenic compounds during uses other advantage of the method ,this work reported by ADDIN EN.CITE ;EndNote;;Cite;;Author;Kaur;/Author;;Year;1987;/Year;;RecNum;24;/RecNum;;DisplayText;(Kaur et al., 1987);/DisplayText;;record;;rec-number;24;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523435210″;24;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Kaur, Preeti;/author;;author;Upadhyay, Sweta;/author;;author;Gupta, VK;/author;;/authors;;/contributors;;titles;;title;Spectrophotometric determination of hydrogen cyanide in air and biological fluids;/title;;secondary-title;Analyst;/secondary-title;;/titles;;periodical;;full-title;Analyst;/full-title;;/periodical;;pages;1681-1683;/pages;;volume;112;/volume;;number;12;/number;;dates;;year;1987;/year;;/dates;;urls;;/urls;;/record;;/Cite;;/EndNote;(Kaur et al., 1987).

Table 4: Determination of generated hydrogen cyanide in air

Table 5: Recovery of hydrogen cyanide from cysteine and whole blood samples

Determination of cyanide in whole blood, erythrocytes, and plasma in which the cyanide stabilized by silver ions is a more sensitive method, first he cyanide transferred from the acidified sample to sodium hydroxide by aeration and then determined calorimetrically by modification K?nig reaction ( Figure 4) with sodium hypochlorite as the chlorinating agent a rapid loss of measurable cyanide found when cyanide was added to plasma in the absence of silver ions was attributed to a reaction with serum albumin. Tthey believed that more sensitive analytical method are require for the use of whole blood cyanide as an indicators of tobacco smokers, this work reported by ADDIN EN.CITE ;EndNote;;Cite;;Author;Lundquist;/Author;;Year;1985;/Year;;RecNum;66;/RecNum;;DisplayText;(Lundquist et al., 1985);/DisplayText;;record;;rec-number;66;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1524907026″;66;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Lundquist, P;/author;;author;Rosling, H;/author;;author;Sörbo, B;/author;;/authors;;/contributors;;titles;;title;Determination of cyanide in whole blood, erythrocytes, and plasma;/title;;secondary-title;Clinical chemistry;/secondary-title;;/titles;;periodical;;full-title;Clinical chemistry;/full-title;;/periodical;;pages;591-595;/pages;;volume;31;/volume;;number;4;/number;;dates;;year;1985;/year;;/dates;;isbn;0009-9147;/isbn;;urls;;/urls;;/record;;/Cite;;/EndNote;(Lundquist et al., 1985).
M
Figure 4: K?nig reaction for determination of cyanide .cyanide first converted to cyanogen chloride by hypochlorite .and cyanogen chloride then reacted with pyridine to produce glutconic aldehyde .which finally coupled with barbituric acid to yield chromogen.
Spectrophotometric based on K?nig reaction for determination of nicotinic acid/ nicotinamide is most popular methods reported in sub-microgram levels during their reaction with cyanogen bromide, the pyridine rings are split by the K?nig reaction and the reaction products coupled with diazotized, p-aminoacctophenonc, p- aminobenzoic acid, sulphanilic acid and H-acid to form coloured azo dyes. The colours formed with nicotinic acid and nicotinamide are of sufficiently different shades to permit use in a rapid visual qualitative test, nicotinic acid/nicotinamide are best differentiated using p-Aminoacetophenone (PAAP) gives a reddish violet colour with nicotinic acid and red colour with nicotinamide which can be easily distinguished and give a deep violet colour if the sample contains a mixture of the two compounds. As a result the p-aminoacetophenonc gives the best for the determination of nicotinic acid/nicotinamide. In addition, the sensitivity of method after this modification is found to be about eight time more than the conventional K?nig reaction, the method was applied to the determination of nicotinic acid/nicotinamide in food, biological and pharmaceutical samples, this work reported by ADDIN EN.CITE ;EndNote;;Cite;;Author;Khan;/Author;;Year;2005;/Year;;RecNum;49;/RecNum;;DisplayText;(Khan et al., 2005);/DisplayText;;record;;rec-number;49;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523606844″;49;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Khan, Seemab;/author;;author;Rai, MK;/author;;author;Gupta, VK;/author;;author;Rai, JK;/author;;/authors;;/contributors;;titles;;title;Determination of small quantities of nicotinic acid in presence of nicotinamide by modified Konig reaction;/title;;/titles;;dates;;year;2005;/year;;/dates;;isbn;0975-0975;/isbn;;urls;;/urls;;/record;;/Cite;;/EndNote;(Khan et al., 2005).

In the presence of surfactants equilibrium, kinetic and spectral properties can be modified some favorable effects are the inhibition of undesirable reactions, such as hydrolysis and photolysis, stabilization of reaction intermediates, cosolubilization of non-polar and polar derivatization reagents and increase in reaction rates such as micellar catalysis ADDIN EN.CITE ;EndNote;;Cite;;Author;Esteve-Romero;/Author;;Year;1995;/Year;;RecNum;90;/RecNum;;DisplayText;(Esteve-Romero et al., 1995b);/DisplayText;;record;;rec-number;90;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1525103167″;90;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Esteve-Romero, J. S.;/author;;author;Simó-Alfonso, E. F.;/author;;author;García-Alvarez-Coque, M. C.;/author;;author;Ramis-Ramos, G.;/author;;/authors;;/contributors;;titles;;title;Micellar enhanced spectrophotometric determination of organic species;/title;;secondary-title;TrAC Trends in Analytical Chemistry;/secondary-title;;/titles;;periodical;;full-title;TrAC Trends in Analytical Chemistry;/full-title;;/periodical;;pages;29-37;/pages;;volume;14;/volume;;number;1;/number;;dates;;year;1995;/year;;pub-dates;;date;1995/01/01/;/date;;/pub-dates;;/dates;;isbn;0165-9936;/isbn;;urls;;related-urls;;url;http://www.sciencedirect.com/science/article/pii/016599369591143G;/url;;/related-urls;;/urls;;electronic-resource-num;https://doi.org/10.1016/0165-9936(95)91143-G;/electronic-resource-num;;/record;;/Cite;;/EndNote;(Esteve-Romero et al., 1995b). in this work presence of surfactants affected on the spectrophotometric analytical procedure for the determination of pyridine derivatives by using the K?nig reaction (Figure 5) like in micellar media of sodium dodecylsulphate (SDS), N-cetyipyridinium chloride and Triton X-100 (Table 6), the sensitivity was largely increased in SDS micellar medium without affected attack of the pyridine ring with cyanogen bromide to produce a glutaconic aldehyde, but the yield of the coupling reaction with an arylamine to produce a polymethine dye was largely increased. Aniline is demonstrated to be superior to other coupling reagents when used in sodium dodecyl sulphate (SDS) micellar solutions. Application was made to the determination of nicotinic acid in pharmaceuticals, this work reported by ADDIN EN.CITE ;EndNote;;Cite;;Author;Esteve-Romero;/Author;;Year;1995;/Year;;RecNum;44;/RecNum;;DisplayText;(Esteve-Romero et al., 1995a);/DisplayText;;record;;rec-number;44;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523603462″;44;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Esteve-Romero, JS;/author;;author;Monferrer-Pons, Ll;/author;;author;Ramis-Ramos, G;/author;;author;Garcia-Alvarez-Coque, MC;/author;;/authors;;/contributors;;titles;;title;Enhanced spectrophotometric determination of nicotinic acid in a sodium dodecyl sulphate micellar medium;/title;;secondary-title;Talanta;/secondary-title;;/titles;;periodical;;full-title;Talanta;/full-title;;/periodical;;pages;737-745;/pages;;volume;42;/volume;;number;5;/number;;dates;;year;1995;/year;;/dates;;isbn;0039-9140;/isbn;;urls;;/urls;;/record;;/Cite;;/EndNote;(Esteve-Romero et al., 1995a).

Figure 5: Reaction for the hydrolysis of pyridine derivatives with cyanogen bromide, and coupling with an arylamine.

Table 6: Wave lengths of maximum absorption (nm) for the aniline polymethine dyes in the presence of surfactants
Compound Non-micellarSodiumdodecyl sulphateN-Cetylpyridinium chloride Triton X-100
Pyridine
PyrrolylmethylpyridineNicotinic acid 480
430 485
485 480
465 490
480
470
*wavelengths measured at PH4.5 and for 0.1M surfactant solutions.
5.2. Micellar liquid chromatographic method
A selective Micellar liquid chromatographic (MLC) method for the automatic precolumn derivatization for determination of pyridine compounds (nicotinamide and nicotinic acid) based on König reaction in pharmaceuticals, serum and urine. Initially the heterocyclic nitrogen of a pyridine derivative reacts with cyanogen bromide and coupled with an arylamine to give a polymethine dye, then reaction coupled to a chromatograph to determine nicotinic acid and nicotinamide after precolumn derivatization, first checked the micellar chromatography behavior of the polymethines using a C18 column. The two vitamins have high polarity with an octanol-water partition coefficient (logPow) of ?0.37 and 0.56 for nicotinamide and nicotinic acid, respectively (Table 7), and their quantification is performed free from interferences by measuring the signal at 440 nm. The result in pharmaceuticals the recoveries obtained depend on the composition stated by the manufacturer, and in serum, urine samples the recoveries are also excellent, this work reported by ADDIN EN.CITE ;EndNote;;Cite;;Author;Capella-Peiró;/Author;;Year;2004;/Year;;RecNum;29;/RecNum;;DisplayText;(Capella-Peiró et al., 2004);/DisplayText;;record;;rec-number;29;/rec-number;;foreign-keys;;key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523437074″;29;/key;;/foreign-keys;;ref-type name=”Journal Article”;17;/ref-type;;contributors;;authors;;author;Capella-Peiró, Maria-Elisa;/author;;author;Carda-Broch, Samuel;/author;;author;Monferrer-Pons, Llorenç;/author;;author;Esteve-Romero, Josep;/author;;/authors;;/contributors;;titles;;title;Micellar liquid chromatographic determination of nicotinic acid and nicotinamide after precolumn König reaction derivatization;/title;;secondary-title;Analytica Chimica Acta;/secondary-title;;/titles;;periodical;;full-title;Analytica Chimica Acta;/full-title;;/periodical;;pages;81-87;/pages;;volume;517;/volume;;number;1;/number;;keywords;;keyword;König reaction;/keyword;;keyword;Precolumn derivatization;/keyword;;keyword;Micellar liquid chromatography;/keyword;;keyword;Nicotinic acid;/keyword;;keyword;Nicotinamide;/keyword;;/keywords;;dates;;year;2004;/year;;pub-dates;;date;2004/07/26/;/date;;/pub-dates;;/dates;;isbn;0003-2670;/isbn;;urls;;related-urls;;url;http://www.sciencedirect.com/science/article/pii/S0003267004005963;/url;;/related-urls;;/urls;;electronic-resource-num;https://doi.org/10.1016/j.aca.2004.05.014;/electronic-resource-num;;/record;;/Cite;;/EndNote;(Capella-Peiró et al., 2004) .

Table 7: Structures, acid–base constants and octanol–water partition coefficients (logPow) for the vitamins and wavelengths of maximum absorption (nm) for the polymethines
Compound Structure
?maxlogKlogPowNicotinic acid
440
nf4.85 0.56
Nicotinamide 445 0.5
3.35 ?0.37
5.3. High-performance liquid chromatographic method
An ion-pair reversed-phase high-performance liquid chromatographic procedure HPLC technique to determine nicotinic acid (NA) and nicotinamide (NAM) in biological materials was developed by applying a post-column derivatization arrangement consisting of two pumps and two knitted tubular reactors, the nicotinic acid and nicotinamide were converted to highly absorbing derivatives by a modified Konig’s reaction (Figure 7). The vitamers were separated within 10 min on an octadecylsilica column applying a linear gradient of tetra-butylammonium phosphate and methanol. The fast separation and quantitation of nicotinic acid and nicotinamide, in addition highly sensitivs, specific and applicable to biological materials is advantage of these method, this work reported by ADDIN EN.CITE <EndNote><Cite><Author>Stein</Author><Year>1995</Year><RecNum>47</RecNum><DisplayText>(Stein et al., 1995)</DisplayText><record><rec-number>47</rec-number><foreign-keys><key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523604005″>47</key></foreign-keys><ref-type name=”Journal Article”>17</ref-type><contributors><authors><author>Stein, J</author><author>Hahn, A</author><author>Rehner, G</author></authors></contributors><titles><title>High-performance liquid chromatographic determination of nicotinic acid and nicotinamide in biological samples applying post-column derivatization resulting in bathmochrome absorption shifts</title><secondary-title>Journal of Chromatography B: Biomedical Sciences and Applications</secondary-title></titles><periodical><full-title>Journal of Chromatography B: Biomedical Sciences and Applications</full-title></periodical><pages>71-78</pages><volume>665</volume><number>1</number><dates><year>1995</year></dates><isbn>0378-4347</isbn><urls></urls></record></Cite></EndNote>(Stein et al., 1995).

Figure 7: Technical set-up: The first reagent (R, 2% chloramine T) was pumped into the eluent stream leaving the column through a T-junction by a Waters M-6ooo HPLC pump (P,) at flow-rate of 0.5 ml/min. After a reactant zone consisting of a 2-m length of PTPE tube (MS; 0.5 mm I.D.) the second reagent (R, 0.25% potassium cyanide, 25 mM TRIS, 40 mhf HCl ) was delivered at a flow-rate of 0.5 ml/min by a Waters M-6000 HPLC pump P2. Thereafter 8-m length of PTIX tube (MS, 0.5 mm I.D.) was mounted to achieve complete derivatization. Both reaction tubes were coiled three-dimensionally to minimize peak broadening and kept at 60C in a water bath (T); D = detector,
I =integrator.

5.4. Spectrofluorimetric determination method
Developed a method based on modified K?nig reaction to quantify both cyanide and thiocyanate determined spectrofluorlmetrically by using the reagents isonicotinic acid and barbituric acid. The technique based on a modified K?nig reaction the reaction involves the formation of cyanogen chloride (CNCl) which is then reacted with pyridine to produce 2-pentenedial derivative this derivative reacts with an aromatic amine to produce aSchiff base that can be detected by a spectrofluorometrically, and the fluorescence properties of the coloured solutions also investigated, the resulting solution excited at 605 nm and the fluorescence was measured at 620 nm , the intermediate was also fluorescent, excitation and emission wavelengths were 527 nm and 556 nm (Figure 8), this work reported by ADDIN EN.CITE <EndNote><Cite><Author>Tanaka</Author><Year>1992</Year><RecNum>17</RecNum><DisplayText>(Tanaka et al., 1992)</DisplayText><record><rec-number>17</rec-number><foreign-keys><key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523431471″>17</key></foreign-keys><ref-type name=”Journal Article”>17</ref-type><contributors><authors><author>Tanaka, Akira</author><author>Deguchi, Kazuhiro</author><author>Deguchi, Toshio</author></authors></contributors><titles><title>Spectrofluorimetric determination of cyanide and thiocyanate based on a modified König reaction in a flow-injection system</title><secondary-title>Analytica Chimica Acta</secondary-title></titles><periodical><full-title>Analytica Chimica Acta</full-title></periodical><pages>281-286</pages><volume>261</volume><number>1</number><keywords><keyword>Fluorimetry</keyword><keyword>Flow system</keyword><keyword>Cyanide</keyword><keyword>König reaction</keyword><keyword>Thiocyanate</keyword></keywords><dates><year>1992</year><pub-dates><date>1992/05/25/</date></pub-dates></dates><isbn>0003-2670</isbn><urls><related-urls><url>http://www.sciencedirect.com/science/article/pii/000326709280203J</url></related-urls></urls><electronic-resource-num>https://doi.org/10.1016/0003-2670(92)80203-J</electronic-resource-num></record></Cite></EndNote>(Tanaka et al., 1992).

520 560 600 640680
Wavelength / nm
Figure 8: Fluorescence spectra Cyanide concentration 0.2 ?M the emission wavelength during measurement of the excitation spectrum was 560 nm and the excitation wavelength for emission measurement was 650nm Slit width 3 nm.

5.5. Gas chromatography- mass spectrometry (GC-MS) method
A method described for simultaneous determination of cyanide CN) and thiocyanate (SCN) in human saliva the samples diluted and the anions separated by an extractive alkylation technique, tetrabutylammonium sulfate was used as phase-transfer catalyst and pentafluorobenzyl bromide as the derivatizing agent and – 2,5dibromotoluene was used as internal standard for quantitation of CN and SCN in saliva and the products analyzed by a gas chromatography-mass spectrometry (GC-MS) with selected ion monitoring method. The method used to examine 10 saliva specimens and the concentration ranged from 4.8 to 29 pmol0.13 -0.75) pg/mL) for CN and 293 to 1029 pmol/L (17-59.7pg/mL) for SCN respectively (Table 8) the SCN results similar to those obtained from a method using oxidation of SCN to CN with colorimetric detection. The procedure may be useful in forensic drug testing when specimen validity testing is required and also in classifying patients as smokers or non-smokers, in addition use in determining some clinical conditions, this work reported by ADDIN EN.CITE <EndNote><Cite><Author>Paul</Author><Year>2006</Year><RecNum>9</RecNum><DisplayText>(Paul and Smith, 2006)</DisplayText><record><rec-number>9</rec-number><foreign-keys><key app=”EN” db-id=”pdv5aa2ah2x5tne5zecpawzgz2xprszwwv2d” timestamp=”1523429342″>9</key></foreign-keys><ref-type name=”Journal Article”>17</ref-type><contributors><authors><author>Paul, Buddha D</author><author>Smith, Michael L</author></authors></contributors><titles><title>Cyanide and thiocyanate in human saliva by gas chromatography-mass spectrometry</title><secondary-title>Journal of analytical toxicology</secondary-title></titles><periodical><full-title>Journal of analytical toxicology</full-title></periodical><pages>511-515</pages><volume>30</volume><number>8</number><dates><year>2006</year></dates><isbn>1945-2403</isbn><urls></urls></record></Cite></EndNote>(Paul and Smith, 2006)
Table 8: cyanid and thiocyanate (mmol/L in ten saliva specimen collected from three male (M) and two female (F) nonsmoking subject

6. Conclusion
In conclusion, The K?nig reaction forms the basis of many analytical methods including those for the determination of nicotinic acid, thiocyanate and cyanide. Due to its toxic nature, a method for its determination has been an area of interest for analytical chemists and numerous methods have been developed and each has its own advantages and disadvantages, most among it the colorimetric methods have been many various problems such as the use of hazardous, often carcinogenic compounds, and the instability of the final color formed as well as of the color reagent itself.

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