Molecular structure of (Z)-6-[(5-chloro-2-hydroxyphenylamino) methylene]-3-(diethylamino)cyclohexa-2,4-dienone: A combined experimental and theoretical study
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Tarih
2011
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Elsevier
Erişim Hakkı
info:eu-repo/semantics/closedAccess
Özet
The crystal structure and spectroscopic properties of ortho-hydroxy Schiff base compound (Z)-6-[(5-chloro-2-hydroxyphenylamino)methylene]-3-(diethylamino)cyclohexa-2,4-dienone were determined by X-ray diffraction, IR and UV-Vis spectroscopy techniques. Molecules of the compound exist as NH tautomeric form in solid state. The gas phase geometry optimizations of two possible tautomeric forms of the title compound were achieved using OFT calculations at B3LYP/6-31G(d,p) level of theory. In order to describe the potential energy barrier belonging to the intramolecular proton transfer and to observe the effects of transfer on the molecular geometry, a relaxed potential energy surface (PES) scan was performed based on the optimized geometry of the NH tautomeric form by varying the redundant internal coordinate, N-H bond distance. At the same level of theory, the vibrational frequencies were calculated and compared with the experimental frequencies. The electronic absorption spectra of the tautomers were calculated using time-dependent density functional theory (TO-OFT) method started from solution phase optimized geometries and compared with the experimental ones. Crown Copyright (c) 2010 Published by Elsevier B.V. All rights reserved.
Açıklama
Anahtar Kelimeler
Schiff base, Tautomerism, Intramolecular proton transfer, HOMA, DFT
Kaynak
Journal of Molecular Structure
WoS Q Değeri
Q2
Scopus Q Değeri
Q1
Cilt
989
Sayı
1-3
