Cyanide selective chemodosimeter in aqueous medium, on test strips and its application in real sample analysis
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Ó Indian Academy of Sciences Sadhana (0123456789().,-volV)FT3](0123456 789().,-volV)
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Cyanide selective chemodosimeter in aqueous medium, on test strips and its application in real sample analysis ASHISH RAINAa, YADVENDRA SINGHb, KOMAL KUMAR YADAVa and TAMAL GHOSHa,* a Department
of Chemistry, Motilal Nehru National Institute of Technology, Allahabad, Prayagraj 211 004, India b Department of Chemistry, University of Allahabad, Prayagraj 211 002, India E-mail: [email protected]; [email protected] MS received 4 October 2019; revised 9 July 2020; accepted 21 July 2020
Abstract. In this paper, synthesis, characterization and detection of CN- by the compound (N0 1E,N0 2E)N0 1,N0 2-bis((2-hydroxynaphthalen-1-yl)methylene)oxalohydrazide (1) have been reported. Compound 1 is synthesized by the reaction of oxalyldihydrazide and 2-hydroxy-1-naphthaldehyde and characterized by FTIR, 1H NMR and ESI-Mass spectroscopy. UV–Visible spectral band of 1 is observed to be broadened and shifted to longer wavelength upon addition of CN- ion selectively in H2O-DMSO (8:2 v/v) medium. Based on the UV–Visible spectral data, the detection limit of cyanide ion for 1 is found to be 30.2 lM. Colourless solution of 1 changes to yellow in the presence of cyanide ion selectively. The same colour change is also observed on Whatman filter paper test strip. Fluorescence intensity of 1 is quenched due to the nucleophilic addition reaction of cyanide with one of the two imine carbons. 1H NMR titration of 1 with CN- ion corroborates the reaction of the latter with one of the two imine carbons of the former, leading to the appearance of cyanomethyl proton signal at 6.15 ppm and consequently, its behaviour as chemodosimeter. The above mentioned chemodosimeter nature of 1 is also validated by ESI-Mass spectroscopy data. Compound 1 is capable for the detection of CN- in water for real samples with concomitant colour change. Keywords. Cyanide selective chemodosimeter; oxalic acid hydrazide; 2-hydroxy-1-naphthaldehyde; addition reaction of cyanide as a nucleophile; real water sample analysis.
1. Introduction Recently, there has been an upsurge in the field of synthetic receptors capable for the selective recognition of anion due to their immense applications in the area of environmental chemistry and mineral exploration.1–5 Among different anions, cyanide (CN-) ion plays a severe detrimental role in living biological systems. The strong binding affinity of cyanide with the active site of cytochrome a3 disrupts mitochondrial electron transport chain, leading to decreased oxidative metabolism in the living cell and finally to cell death.6–13 Cyanide, entered through the gastrointestinal tract, lungs, skin etc., is responsible for convulsion, vomiting and loss of consciousness in human body.14–16 Despite such drastic toxicity, cyanide is
utilized in the synthesis process of several industrial products such as nylon, fertilizers as well as electroplating industry.17–20 Indiscriminate discharge of cyanide through industrial effluen
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