N-[4-(3-Methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-N′-pyridin-2-ylmethylene-chloro-acetic acid hydrazide: Synthesis and configurational assignment based on X-ray, {sup 1}H, and {sup 13}C NMR and theoretical calculations

• Published in: Crystallography reports 2017-11, Vol.62 (6)
• Main Authors: Demir, Sibel, Dinçer, Muharrem, Çukurovali, Alaaddin, Yılmaz, Ibrahim
• Format: Article
• Language: English
• Subjects: ACETIC ACID; BONDING; CARBON 13; CHEMICAL SHIFT; COMPARATIVE EVALUATIONS; CONDENSED MATTER PHYSICS, SUPERCONDUCTIVITY AND SUPERFLUIDITY; DENSITY FUNCTIONAL METHOD; ENERGY SPECTRA; GAUGE INVARIANCE; HYDRAZIDES; HYDROGEN; HYDROGEN 1; MOLECULES; NUCLEAR MAGNETIC RESONANCE; POTENTIAL ENERGY; THIAZOLES; VALIDATION; X RADIATION
• ISSN: 1063-7745; 1562-689X
• DOI: 10.1134/S1063774517060086

In this study, quantum chemical calculations based on the density functional theory have been carried out to examine the effects of N-[4-(3-methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-N′-pyridin-2-ylmethylene- chloro-acetic acid hydrazide. The calculated values are compared with the experimental data available for these molecules as a mean of validation of our proposed chemistry model. Aided by normal coordinate analysis and potential energy distributions, a confident vibrational assignment of all fundamentals is proposed herein. Additional support is given by {sup 1}H and {sup 13}C NMR spectra recorded with the sample dissolved in CDCl{sub 3} and by predicted chemical shifts at the B3LYP/6-31G(d)/6-311G+(d) levels obtained using the gauge-invariant atomic orbital method. The calculated HOMO and LUMO energies also confirm that the charge transfer occurs within the molecule. Thiazole-based compounds are potential storehouse for exploiting CH···O and CH···N hydrogen bonding interactions for molecular self-assembly.