Journal of Molecular Structure, ( ISI ), Volume (1112), Year (2016-5) , Pages (87-96)

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

Authors: Ayoub Kanaani , Davood Ajloo , Gholamhossein Grivani , Abbaseh Ghavami , Mohamad Vakili ,

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Abstract

Abstract The experimental and theoretical studies on asymmetrical Schiff base, salicylideneimino-ethylimino-pentan-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 1H 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-2-one)APO(. In addition, natural atomic charges, global reactivity parameters, and HOMO–LUMO gaps have also been discussed.

Keywords

Schiff base; Tautomerism; DFT; 1H NMR and UV spectra
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@article{paperid:1055165,
author = {Ayoub Kanaani and Davood Ajloo and Gholamhossein Grivani and Abbaseh Ghavami and Vakili, Mohamad},
title = {Tautomeric stability, molecular structure, NBO, electronic and NMR analyses of salicylideneimino-ethylimino-pentan-2-one},
journal = {Journal of Molecular Structure},
year = {2016},
volume = {1112},
month = {May},
issn = {0022-2860},
pages = {87--96},
numpages = {9},
keywords = {Schiff base; Tautomerism; DFT; 1H NMR and UV spectra},
}

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%0 Journal Article
%T Tautomeric stability, molecular structure, NBO, electronic and NMR analyses of salicylideneimino-ethylimino-pentan-2-one
%A Ayoub Kanaani
%A Davood Ajloo
%A Gholamhossein Grivani
%A Abbaseh Ghavami
%A Vakili, Mohamad
%J Journal of Molecular Structure
%@ 0022-2860
%D 2016

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