Tautomeric stability, molecular structure, NBO, electronic and NMR analyses of salicylideneimino-ethylimino-pentan-2-one

被引：32
|
作者：
Kanaani, Ayoub [1 ]
Ajloo, Davood [1 ]
Grivani, Gholamhossein [1 ]
Ghavami, Abbaseh [1 ]
Vakili, Mohammad [2 ]
机构：
[1] Damghan Univ, Sch Chem, Damghan 36715364, Iran
[2] Ferdowsi Univ Mashhad, Dept Chem, Mashhad 917751436, Iran
来源：
JOURNAL OF MOLECULAR STRUCTURE | 2016年 / 1112卷
关键词：
Schiff base; Tautomerism; DFT; H-1 NMR and UV spectra; NONLINEAR-OPTICAL PROPERTIES; VIBRATIONAL-SPECTRA; INORGANIC CHROMOPHORES; CRYSTAL-STRUCTURE; COMPLEXES; COPPER(II); HYPERPOLARIZABILITIES; NICKEL(II); CATALYSIS; ZINC(II);
D O I：
10.1016/j.molstruc.2016.02.024
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
The experimental and theoretical studies on asymmetrical Schiff base, salicylideneimino-ethyliminopentan-2-one (SEIPO) were studied. The tautomerism of SEIPO was also studied by calculations using density functional theory (DFT). Two of the four tautomers were shown to coexist. Tautomerism and the effect of solvent on the tautomeric equilibria in the gas phase and in different solvents were studied. According to calculated results, L3, L4 tautomers are more stable than the L1, L2 tautomers. The H-1 NMR spectra give the additional evidence for the coexistence of the tautomers keto-amine and enol-imine for SEIPO. UV vis spectra of SEIPO were recorded in various organic solvents to check the dependence of tautomerism on solvent types. The theoretical calculations and spectroscopic results indicate that the intramolecular hydrogen bonding (IHB) strength of SEIPO is stronger than that in 4-amino-3-penten-2one)APO(. In addition, natural atomic charges, global reactivity parameters, and HOMO-LUMO gaps have also been discussed. (C) 2016 Elsevier B.V. All rights reserved.
引用
收藏
页码：87 / 96
页数：10
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