Effect of Substituents on Methylenecyclobutane /  1-Methylcyclobutene System

Ghassab M. Al-Mazaideh; Rabia A. Enwisry; Salim M. Khalil

doi:10.9734/IRJPAC/2016/28006

Research Article Open access CC BY 4.0

Effect of Substituents on Methylenecyclobutane / 1-Methylcyclobutene System

Ghassab M. Al-Mazaideh, Rabia A. Enwisry, Salim M. Khalil

International Research Journal of Pure and Applied Chemistry · pp. 1–10 · Published 10 Aug 2016

10.9734/IRJPAC/2016/28006

Abstract

A theoretical study was performed on the methylenecyclobutane and 1-methylcyclobutene in the gas and aqueous phases using PM3 and DFT calculations. Methylenecyclobutane was found to be more stable than 1-methylcyclobutene in the gas and aqueous phases according to PM3 calculations, and only slightly more stable than 1-methylcyclobutene in the case of DFT calculations. Also the effect of substituents (X = F, CH3, NH2, CN, NO2, CHO and CF3) was studied on the relative stabilities of these two tautomers. It was found that all the substituents increase the stability of 1-methylcyclobutene in the gas and aqueous phases. Heats of formation, and electron densities, were reported. The stability effect of X- substituents on the methylenecyclobutane and 1-methylcyclobutene was explained by Gibbs free energies calculations and confirmed by isodesmic reactions.

Cyclic alkene tautomerism PM3 DFT substituents

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Ghassab M. Al-Mazaideh, Rabia A. Enwisry, Salim M. Khalil (2016). Effect of Substituents on Methylenecyclobutane / 1-Methylcyclobutene System. International Research Journal of Pure and Applied Chemistry , 1–10. https://doi.org/10.9734/IRJPAC/2016/28006

Affiliations

Ghassab M. Al-Mazaideh — Department of Chemistry and Chemical Technology, Faculty of Science, Tafila Technical University, P.O.Box 179, Tafila 66110, Jordan
Rabia A. Enwisry — Department of Chemistry, School of Basic Science, Libyan Academy for Graduate Studies, P.O.Box 17979031, Tripoli, Libya
Salim M. Khalil — Department of Chemistry and Chemical Technology, Faculty of Science, Tafila Technical University, P.O.Box 179, Tafila 66110, Jordan

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