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, cilt.2020, sa.30, ss.4681-4692, 2020 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 2020 Sayı: 30
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1002/ejoc.202000342
  • Dergi Adı: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Applied Science & Technology Source, CAB Abstracts, Chimica
  • Sayfa Sayıları: ss.4681-4692
  • Anahtar Kelimeler: 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
  • Gazi Üniversitesi Adresli: Evet

Özet

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.