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2 fragments is 173 kcal/mol. Subtracting the value for the rotational barrier in ethylene (65 kcal/mol) leaves a σ-bonding energy of 108 kcal/mol. This value is larger than the bond strength in ethane of 90 kcal/mol, as to be expected on the basis of hybridization arguments. However, a better estimate of the π-bonding in ethylene corrects for the significant hyperconjugative stabilization presented above. The hypercon-jugative stabilization is added to the rotational barrier (65 + 14.7 kcal/mol = 79.7 kcal/mol), and this is subtracted from the BDE of ethylene yielding a σ-bonding energy of 93.3 kcal/mol, only slightly larger than the bond energy in ethane.
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106
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33745491214
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note
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This is a simplistic method, since it assumes that the hyperconjugative contribution in the transition state to rotation of ethylene does not change for the substituted species. A few reasons to expect some change are differences in C-C vs C-H hyperconjugative stabilization and changes in bond lengths and angles.
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