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Homoconjugation of Some Organic Bases in Acetonitrile

Stańczyk-Dunaj M., Jarczewski A.

Polish Journal of Chemistry

2005

Vol. 79 / nr 6

1025-1032

The largest value of the homoconjugation constant in acetonitrile has been found for tribenzylamine KHOMO = 7.73 and the lower for N-methylpiperidine KHOMO = 3.44. For triethylamine, tri-n-propylamine, tributylamine, 1,3-diphenylguanidine, 2-tert-butyl- 1,1',3,3'-tetramethylguanidine, 1,1',2,2',3-pentamethylguanidine, 1,8-bis(dimethylamino) naphthalene, and 1,5,7-triazabicyclo[4.4.0]dec-5-ene bases no homoconjugated complexes BH+B were formed. Additionally the basicity of tribenzylamine pKa = 16.13, 1,3-diphenylguanidine pKa = 18.79, 1,1',2,2',3-pentamethylguanidine pKa = 23.12, and 2-tert-butyl-1,1',3,3'-tetramethylguanidine pKa = 23.56 in acetonitrile are given.