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

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
* Author to whom correspondence should be addressed.
Received: 24 September 2012; in revised form: 29 October 2012 / Accepted: 29 October 2012 / Published: 20 November 2012
PDF Full-text Download PDF Full-Text [547 KB, Updated Version, uploaded 21 November 2012 14:38 CET]
The original version is still available [547 KB, uploaded 20 November 2012 14:10 CET]
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.
Keywords: acetaldehyde; eclipsed; bisected; vinyl alcohol; tautomerization; hyperconjugation; MP2; B3LYP; NBO

Article Statistics

Load and display the download statistics.

Citations to this Article

Cite This Article

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.

AMA Style

Osman OI, Alyoubi AO, Elroby SAK, Hilal RH, Aziz SG. Eclipsed Acetaldehyde as a Precursor for Producing Vinyl Alcohol. International Journal of Molecular Sciences. 2012; 13(11):15360-15372.

Chicago/Turabian Style

Osman, Osman I.; Alyoubi, Abdulrahman O.; Elroby, Shabaan A.K.; Hilal, Rifaat H.; Aziz, Saadullah G. 2012. "Eclipsed Acetaldehyde as a Precursor for Producing Vinyl Alcohol." Int. J. Mol. Sci. 13, no. 11: 15360-15372.

Int. J. Mol. Sci. EISSN 1422-0067 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert