Carbocation mediated alpha-hydride abstraction from amines

CHED 359

Erin Herman, eh0264@ship.edu, Allison H. Predecki, ahpred@ship.edu, and Daniel P. Predecki, dppred@ship.edu. Department of Chemistry, Shippensburg University, 1871 Old Main Drive, Shippensburg, PA 17257

Carbonium ions are known to remove a hydride alpha to an amine, to form an iminium ion.  The reactivity of tris(4-(dimethylamino)phenyl) carbonium ion, tris(4-methoxyphenyl) carbonium ion and triphenyl carbonium ion, with triisoctylamine, tripropylamine, tributylamine and triethylamine will be determined by UV-visible spectrophotometry in acetonitrile.  Trapping studies of the iminium ion with sodium methoxide will also be performed. Based on the quantitative data, a structure-reactivity profile will be obtained.