Issue 9, 2004
From the journal:

Organic & Biomolecular Chemistry

Thermochemistry of biphenylcarboxylic and dicarboxylic acids. A combined experimental and theoretical study†

M. Agostinha R. Matos,*a   Margarida S. Miranda,a   Diana V. S. S. Martins,a   Natália A. B. Pinto,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 standard molar enthalpies of combustion and sublimation of 2- and 4-biphenylcarboxylic acid, 2,2′- and 4,4′-biphenyldicarboxylic acid were measured and the gas-phase enthalpies of formation, at T = 298.15 K, were determined. Ab initio calculations were performed and a theoretical study on molecular structure of all the biphenyl acid isomers has been carried out. Calculated enthalpies of formation using appropriate isodesmic reactions are compared with experimental values, and a good agreement is observed. Estimates of enthalpies of formation for the isomers, which were not studied experimentally, are presented. All the acids containing at least one ortho COOH are comparatively less stable than their isomers having just meta or para COOH group(s).

Graphical abstract: Thermochemistry of biphenylcarboxylic and dicarboxylic acids. A combined experimental and theoretical study

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Article information

DOI
https://doi.org/10.1039/B401605J
Article type
Paper
Submitted
03 Feb 2004
Accepted
05 Mar 2004
First published
29 Mar 2004

Org. Biomol. Chem., 2004,2, 1353-1358

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Thermochemistry of biphenylcarboxylic and dicarboxylic acids. A combined experimental and theoretical study

M. A. R. Matos, M. S. Miranda, D. V. S. S. Martins, N. A. B. Pinto, V. M. F. Morais and J. F. Liebman, Org. Biomol. Chem., 2004, 2, 1353 DOI: 10.1039/B401605J

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