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Equilibrium acidities and homolytic bond dissociation energies of the acidicC-H bonds in N-substituted trimethylammonium and pyridinium cations
- Source :
- Journal of Organic Chemistry. May 21, 1993, Vol. 58 Issue 11, p3060, 7 p.
- Publication Year :
- 1993
-
Abstract
- The effects of the alpha-Me3N+ andalpha-PyN+ groups on equilibrium acidities were determined, specifically their effects on carbon-acid substrates such as acetone, diethyl malonate, fluorene, 2-(phenyl-sulfonyl)fluorene, toluene, p-(phenylsulfonyl)toluene and others. Thetrimethylammonium and pyridinium groups had acidifying effects on the adjacent C-H bonds associated with coulombic stabilization of the negative charge by positive charges on the nitrogen atom. Pyridinium groups had opposite effects on adjacent radicals because they caused destabilization.
Details
- ISSN :
- 00223263
- Volume :
- 58
- Issue :
- 11
- Database :
- Gale General OneFile
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- edsgcl.14010078