Tweezer-shaped hydrazone derivatives for the selective detection of cyanide ion

• Published in: Journal of inclusion phenomena and macrocyclic chemistry 2020-02, Vol.96 (1-2), p.181-195
• Main Authors: Sahoo, Priya Ranjan, Kumar, Arvind, Choudhary, Shikha, Hitaish, Chhikara, Rocky, Malik, Kalpana, Nirwan, Sonam, Seth, Charu, Duggal, Garima, Kumar, Satish
• Format: Article
• Language: English
• Subjects: Acetonitrile; Binding; Chemistry; Chemistry and Materials Science; Color; Crystallography and Scattering Methods; Food Science; Hydrazones; NMR; Nuclear magnetic resonance; Organic Chemistry; Original Article; Parameters; Protons; Receptors; Selectivity
• ISSN: 1388-3127; 1573-1111
• DOI: 10.1007/s10847-019-00963-1

A series of hydrazone moiety based probes with variable size of binding cavity flanked by mono-nitro and di-nitro group were synthesized. Characterization of the synthesized probes was performed by using 1 H, 13 C-NMR, HR-MS and FT-IR spectral techniques. Owing to the presence of N–H moieties and nitro groups in the synthesized structures, the probes were evaluated for the detection of anions. The synthesized receptors selectively detected cyanide ions in acetonitrile solution and displayed a distinct change in color. The change in color and selectivity was observed to be dependent on the cage-size and the number of nitro groups present in the structure of the probe. The DFT studies were also performed to understand the mode of binding and color observed in the probes. The parameters obtained from the DFT data correlated very well with the parameters obtained from experimental data. DFT studies indicated that the abstraction of the second proton is more difficult than the abstraction of the first proton due to the presence of H-bonds. Graphic Abstract