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Cycloalkane and cycloalkene C-H bond dissociation energies.
- Source :
-
Journal of the American Chemical Society [J Am Chem Soc] 2006 Dec 27; Vol. 128 (51), pp. 17087-92. - Publication Year :
- 2006
-
Abstract
- Both C-H bond dissociation energies for cyclobutene were measured in the gas phase (BDE = 91.2 +/- 2.3 (allyl) and 112.5 +/- 2.5 (vinyl) kcal mol-1) via a thermodynamic cycle by carrying out proton affinity and electron-binding energy measurements on 1- and 3-cyclobutenyl anions. The results were compared to those for an acyclic model compound, cis-2-butene, and provide the needed information to experimentally establish the heat of formation of cyclobutadiene. Chemically accurate G3 and W1 calculations also were carried out on cycloalkanes, cycloalkenes, and selected reference compounds. It appears that commonly cited bond energies for cyclopropane, cyclobutane, and cyclohexane are 3 to 4 kcal mol-1 too small and their pi bond strengths, as given by BDE1 - BDE2, are in error by up to 8 kcal mol-1.
Details
- Language :
- English
- ISSN :
- 0002-7863
- Volume :
- 128
- Issue :
- 51
- Database :
- MEDLINE
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 17177461
- Full Text :
- https://doi.org/10.1021/ja065348u