A new mechanism for selective recognition of cyanide in organic and aqueous solution


Keles E., AYDINER B. , NURAL Y., SEFEROĞLU N. , ŞAHİN E., SEFEROĞLU Z.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol.2020, no.30, pp.4681-4692, 2020 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 2020 Issue: 30
  • Publication Date: 2020
  • Doi Number: 10.1002/ejoc.202000342
  • Title of Journal : EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  • Page Numbers: pp.4681-4692
  • Keywords: Colorimetric Chemosensor, Fluorimetric Chemosensor, Selective cyanide detection, Nucleophilic aromatic substitution of hydrogen (NASH), SNH, Benzisoxazole, HETEROCYCLIC NITRO-COMPOUNDS, NUCLEOPHILIC-SUBSTITUTION, POTASSIUM CYANIDE, FLUORESCENT-PROBE, SCHIFF-BASE, FLUORIDE, CHEMOSENSOR, HYDROGEN, ANIONS, SENSOR

Abstract

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 chemosensorDNBAshowed 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/H2O: 8:2, v/v). The intensive colorimetric and fluorimetric color changes were observed in ambient light and UV-light (lambda(ex). 365 nm) after cyanide interacted withDNBA. A method that can be used in the synthesis of new biologically active benzisoxazole compound was described by the reaction ofDNBAwith TBACN and KCN in DMSO or DMSO/H2O, respectively. All interaction mechanisms betweenDNBAand cyanide and fluoride anions were demonstrated by experimental studies using various spectroscopic methods such as UV/Vis, fluorescence,H-1/C-13 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.