Experimental and computational bridgehead C-H bond dissociation enthalpies

Alireza Fattahi, Lev G Lis, Zahra A. Tehrani, Sudha S. Marimanikkuppam, Steven R Kass

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11 Scopus citations


Bridgehead C-H bond dissociation enthalpies of 105.7 ± 2.0, 102.9 ± 1.7, and 102.4 ± 1.9 kcal mol -1 for bicyclo[2.2.1]heptane, bicyclo[2.2.2]octane, and adamantane, respectively, were determined in the gas phase by making use of a thermodynamic cycle (i.e., BDE(R-H) = ΔH° acid(H-X) - IE(H ) + EA(X )). These results are in good accord with high-level G3 theory calculations, and the experimental values along with G3 predictions for bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[3.1.1]heptane, and bicyclo[4.2.1]nonane were found to correlate with the flexibility of the ring system. Rare examples of alkyl anions in the gas phase are also provided.

Original languageEnglish (US)
Pages (from-to)1909-1914
Number of pages6
JournalJournal of Organic Chemistry
Issue number4
StatePublished - Feb 17 2012


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