Issue 16, 2003
From the journal:

Organic & Biomolecular Chemistry

Thermochemistry of (E)- and (Z)-disubstituted alkene species: a combined experimental and theoretical investigation of isomeric dimethyl fumarate and dimethyl maleate

M. Agostinha R. Matos,*a   Margarida S. Miranda,a   Victor M. F. Moraisab  and  Joel F. Liebmanc  

* Corresponding authors

a Centro de Investigação em Química, Departamento de Química, Faculdade de Ciências da Universidade do Porto, Rua do Campo Alegre, 687, P-4169-007 Porto, Portugal
E-mail: marmatos@fc.up.pt

b Instituto de Ciências Biomédicas Abel Salazar, Universidade do Porto, P-4099-003 Porto, Portugal

c Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, MD 21250, USA

Abstract

The first unequivocal thermochemical/calorimetric determination of the enthalpies of combustion, phase change, and formation of a pair of (E)- and (Z)-disubstituted olefins of the type XCH[double bond, length as m-dash]CHX, where X is an electron withdrawing group, is reported in this paper for the isomeric species dimethyl fumarate and dimethyl maleate (X = COOCH3). The corresponding density functional calculations, corrected for vibrational and thermal effects, confirm that the former isomer is more stable by some 30 kJ mol−1.

Graphical abstract: Thermochemistry of (E)- and (Z)-disubstituted alkene species: a combined experimental and theoretical investigation of isomeric dimethyl fumarate and dimethyl maleate

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Article information

DOI
https://doi.org/10.1039/B303276K
Article type
Paper
Submitted
25 Mar 2003
Accepted
09 Jun 2003
First published
10 Jul 2003

Org. Biomol. Chem., 2003,1, 2930-2934

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Thermochemistry of (E)- and (Z)-disubstituted alkene species: a combined experimental and theoretical investigation of isomeric dimethyl fumarate and dimethyl maleate

M. A. R. Matos, M. S. Miranda, V. M. F. Morais and J. F. Liebman, Org. Biomol. Chem., 2003, 1, 2930 DOI: 10.1039/B303276K

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