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Thermochemical Properties of the Benzynes

Paul G. Wenthold ^A

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^A The Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47906, USA. Email: pgw@purdue.edu

Australian Journal of Chemistry 63(7) 1091-1098 https://doi.org/10.1071/CH10126
Submitted: 18 March 2010 Accepted: 24 May 2010 Published: 15 July 2010

Abstract

The thermochemical properties of the benzynes have been the subject of investigation for nearly 50 years. This work provides an overview and assessment of all the experimental thermochemical properties that have been reported for the benzynes, or can be derived from reported thermochemical data. These properties include enthalpies of formation and thermochemical values that correspond to formation and dissociation of the benzynes by neutral and ionic processes. Thermochemical values are provided for both the ground-state singlet and the excited-state triplet states of the benzynes. The starting point for all the thermochemical consideration of the benzynes are the enthalpies of formation, which, in this work, are recommend to be 107.3 ± 3.5, 121.9 ± 3.1, and 138.0 ± 1.0 kcal mol^–1 for ortho-, meta-, and para-benzyne, respectively (1 kcal mol^–1 = 4.184 kJ mol^–1). Whereas the paper predominantly focuses on the experimentally determined values, it also provides a comparison with theoretical studies that have examined the absolute thermochemical properties of the benzynes.

Acknowledgements

The author’s contributions to this field in the past 20 years have been supported by the National Science Foundation and the Petroleum Research Fund of the American Chemical Society. However, most of the credit for the work goes to the late Professor Robert Squires, who provided the means as well as much of the motivation for these investigations. The results described herein are very much a legacy of his life’s work, to which I am honoured to have contributed. Thanks also go to the other coworkers who have contributed along the way, as advisers, students, and collaborators, in the studies of benzynes and related molecules.

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