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Equilibrium acidities and homolytic bond dissociation enthalpies of the acidic C-H bonds in As-substituted triphenylarsonium and related cations
- Source :
- Journal of Organic Chemistry. Oct 2, 1998, 7072
- Publication Year :
- 1998
-
Abstract
- The acidifying effects of an alpha-triphenylphosphonium family are found to be around 9-20 pK units stronger than related alpha-trimethylammonium on adjacent C-H bonds. The effects of alpha-triphenylarsoinium groups on the equilibrium acidity and the bond dissociation enthalpies (BDEs) of adjacent acidic C-H bonds have been studied. Acidifying effects were found to be 13-20 pK units and were due to the combined Coulombic and polarizable interaction on the ylide anions. The BDEs show that alpha-triphenylarsonium addition decreases adjacent radical stabilities by 2-5 kcal/mol.
Details
- ISSN :
- 00223263
- Database :
- Gale General OneFile
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- edsgcl.53348402