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Title: 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

Abstract

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.

Authors:
 [1];  [2];  [3];  [4]
  1. Gaziantep University, Technical Science Vocational High School (Turkey)
  2. Ondokuz Mayıs University, Department of Physics, Faculty of Arts and Sciences (Turkey)
  3. Firat University, Department of Chemistry, Faculty of Science (Turkey)
  4. University of Karamanoğlu Mehmet Bey, Department of Chemistry, Faculty of Science (Turkey)
Publication Date:
OSTI Identifier:
22758328
Resource Type:
Journal Article
Journal Name:
Crystallography Reports
Additional Journal Information:
Journal Volume: 62; Journal Issue: 6; Other Information: Copyright (c) 2017 Pleiades Publishing, Inc.; Country of input: International Atomic Energy Agency (IAEA); Journal ID: ISSN 1063-7745
Country of Publication:
United States
Language:
English
Subject:
75 CONDENSED MATTER PHYSICS, SUPERCONDUCTIVITY AND SUPERFLUIDITY; ACETIC ACID; BONDING; CARBON 13; CHEMICAL SHIFT; COMPARATIVE EVALUATIONS; DENSITY FUNCTIONAL METHOD; ENERGY SPECTRA; GAUGE INVARIANCE; HYDRAZIDES; HYDROGEN; HYDROGEN 1; MOLECULES; NUCLEAR MAGNETIC RESONANCE; POTENTIAL ENERGY; THIAZOLES; VALIDATION; X RADIATION

Citation Formats

Demir, Sibel, Dinçer, Muharrem, Çukurovali, Alaaddin, and Yılmaz, Ibrahim. 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. United States: N. p., 2017. Web. doi:10.1134/S1063774517060086.
Demir, Sibel, Dinçer, Muharrem, Çukurovali, Alaaddin, & Yılmaz, Ibrahim. 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. United States. doi:10.1134/S1063774517060086.
Demir, Sibel, Dinçer, Muharrem, Çukurovali, Alaaddin, and Yılmaz, Ibrahim. Wed . "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". United States. doi:10.1134/S1063774517060086.
@article{osti_22758328,
title = {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},
author = {Demir, Sibel and Dinçer, Muharrem and Çukurovali, Alaaddin and Yılmaz, Ibrahim},
abstractNote = {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.},
doi = {10.1134/S1063774517060086},
journal = {Crystallography Reports},
issn = {1063-7745},
number = 6,
volume = 62,
place = {United States},
year = {2017},
month = {11}
}