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Int. J. Mol. Sci. 2012, 13(11), 15360-15372; doi:10.3390/ijms131115360

Eclipsed Acetaldehyde as a Precursor for Producing Vinyl Alcohol

Chemistry Department, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia
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Received: 24 September 2012 / Revised: 29 October 2012 / Accepted: 29 October 2012 / Published: 20 November 2012
(This article belongs to the Section Physical Chemistry, Theoretical and Computational Chemistry)
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Abstract

The MP2 and DFT/B3LYP methods at 6-311++G(d,p) and aug-cc-pdz basis sets have been used to probe the origin of relative stability preference for eclipsed acetaldehyde over its bisected counterpart. A relative energy stability range of 1.02 to 1.20 kcal/mol, in favor of the eclipsed conformer, was found and discussed. An NBO study at these chemistry levels complemented these findings and assigned the eclipsed acetaldehyde preference mainly to the vicinal antiperiplanar hyperconjugative interactions. The tautomeric interconversion between the more stable eclipsed acetaldehyde and vinyl alcohol has been achieved through a four-membered ring transition state (TS). The obtained barrier heights and relative stabilities of eclipsed acetaldehyde and the two conformers of vinyl alchol at these model chemistries have been estimated and discussed. View Full-Text
Keywords: acetaldehyde; eclipsed; bisected; vinyl alcohol; tautomerization; hyperconjugation; MP2; B3LYP; NBO acetaldehyde; eclipsed; bisected; vinyl alcohol; tautomerization; hyperconjugation; MP2; B3LYP; NBO
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Osman, O.I.; Alyoubi, A.O.; Elroby, S.A.K.; Hilal, R.H.; Aziz, S.G. Eclipsed Acetaldehyde as a Precursor for Producing Vinyl Alcohol. Int. J. Mol. Sci. 2012, 13, 15360-15372.

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