Issue 16, 2003

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

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

Article information

Article type
Paper
Submitted
25 Mar 2003
Accepted
09 Jun 2003
First published
10 Jul 2003

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

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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