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Cyanide Reaction with Ninhydrin: Elucidation of Reaction and Interference Mechanisms

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Abstract

A new sensitive spectrophotometric method has recently been developed for the trace determination of cyanide with ninhydrin. Cyanide ion was supposed to act as a specific base catalyst. Nevertheless, this paper demonstrates that the reported assay is based on a novel reaction of cyanide with 2,2-dihydroxy-1,3-indanedione, which affords purple or blue colored salts of 2-cyano-1,2,3-trihydroxy-2H indene. Hydrindantin is merely an intermediary of the reaction. The formation of a stable and isolable ninhydrin-cyanide compound has been confirmed by its preparation in crystalline form. Also, it is thoroughly characterized by elemental as well as MS, IR, UV/VIS and 1H NMR analyses. The Ruhemann’s sequence of reactions of cyanide with ninhydrin has been reconsidered and an adequate mechanism of the reaction is proposed. As a consequence, the interference of oxidizers as well as copper, silver and mercury ions with the cyanide determination has been elucidated.

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Authors and Affiliations

  1. Organic Chemistry and Biochemistry Department, Al. I. Cuza University of Iasi, 11 Carol I, Iasi-, 700506, Romania

    Gabi Drochioiu, Ionel Mangalagiu, Karin Popa & Ioan Druta

  2. Petru Poni Institute of Macromolecular Chemistry, 41a Ghica Voda, Iasi-, 700487, Romania

    Ecaterina Avram

  3. Analytical Chemistry Department, Al. I. Cuza University of Iasi, 11 Carol I, Iasi-, 700506, Romania

    Alin Constantin Dirtu

Authors
  1. Gabi Drochioiu
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  2. Ionel Mangalagiu
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  3. Ecaterina Avram
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  4. Karin Popa
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  5. Alin Constantin Dirtu
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  6. Ioan Druta
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Correspondence to Gabi Drochioiu.

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Drochioiu, G., Mangalagiu, I., Avram, E. et al. Cyanide Reaction with Ninhydrin: Elucidation of Reaction and Interference Mechanisms. ANAL. SCI. 20, 1443–1447 (2004). https://doi.org/10.2116/analsci.20.1443

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  • DOI: https://doi.org/10.2116/analsci.20.1443

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