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Investigation of the molecular structure of 4‐(3‐methyl‐3‐phenylcyclobutyl)‐2‐[2‐(3‐methylbenzylidene)hydrazinyl]thiazole in the gas and solid phases
Author(s) -
Karakurt Tuncay
Publication year - 2018
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229618013475
Subject(s) - tautomer , dihedral angle , natural bond orbital , density functional theory , intermolecular force , crystallography , hydrogen bond , crystal structure , chemistry , molecular orbital , thiazole , computational chemistry , crystal (programming language) , molecular geometry , materials science , molecule , stereochemistry , organic chemistry , computer science , programming language
In this study, the title Shiff base, C 22 H 23 N 3 S, was synthesized and examined by 1 H and 13 C NMR spectroscopy and X‐ray analysis techniques. The crystal structure is stabilized by classical intermolecular N—H…N hydrogen bonding. The crystal packing is additionally stabilized by C—H…π interactions. It has been observed that the compound can exist in two different tautomeric forms, and experimental and theoretical studies were carried out on these tautomeric structures. For this purpose, the gas phase of the compound was optimized by density functional theory (DFT) using the B3LYP/6‐311G(d) method, which allowed for the structural parameters (bond angles, bond lengths and dihedral angles), as well as the frontier molecular orbitals (FMO), to be examined. In addition, stable structures of the two tautomers in the solid phase were obtained using Quantum ESPRESSO under periodic boundary conditions (PBC).