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A new mechanism for selective recognition of cyanide in organic and aqueous solution
Author(s) -
Keleş Ergin,
Aydıner Burcu,
Nural Yahya,
Seferoğlu Nurgül,
Şahin Ertan,
Seferoğlu Zeynel
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000342
Subject(s) - chemistry , cyanide , chromogenic , deprotonation , aqueous solution , fluorescence , medicinal chemistry , organic chemistry , ion , chromatography , physics , quantum mechanics
A simple colorimetric and fluorimetric chemosensor 3,5‐dinitro‐( N ‐phenyl)benzamide ( DNBA ), was synthesized for selective determination of cyanide anion in organic and aqueous solutions via novel chemodosimeter approach. The chemosensor DNBA showed a chromogenic and fluorogenic selective response to CN – against competing anions such as F – , AcO – , and H 2 PO 4 – in organic (DMSO and ACN) and in aqueous solutions (in DMSO/H 2 O: 8:2, v/v). The intensive colorimetric and fluorimetric color changes were observed in ambient light and UV‐light (λ ex . 365 nm) after cyanide interacted with DNBA . A method that can be used in the synthesis of new biologically active benzisoxazole compound was described by the reaction of DNBA with TBACN and KCN in DMSO or DMSO/H 2 O, respectively. All interaction mechanisms between DNBA and cyanide and fluoride anions were demonstrated by experimental studies using various spectroscopic methods such as UV/Vis, fluorescence, 1 H/ 13 C NMR, and mass spectrometry as well as X‐ray diffraction method. In addition, the experimental results were also explained with theoretical data. The spectroscopic results showed that cyanide interacts with three different mechanisms; deprotonation, nucleophilic aromatic substitution, and formation of benzisoxazole ring.