The ortho-effect in 2-amino- and 2-methylamino-benzylidyne trifluoride, (2-trifluoromethyl- and 2-trifluoromethyl-N-methyl-aniline)

Abstract

Attempts to synthesise 2-dimethylaminobenzylidyne trifluoride (2-trifluoromethyl-NN-dimethyl aniline) have, so far, been unsuccessful. The possible relevance of steric factors and intramolecular hydrogen bonding operative in 2-amino- and 2-methylaminobenzylidyne trifluoride (2-trifluoromethyl- and 2-trifluoromethyl-N-methyl-anline) is discussed by comparing observed and calculated dipole moments of these compounds and by assessing their tendencies to undergo intermolecular hydrogen bonding to dioxan.