Abstract
The effect of addition of small amounts of hydrogen-bond acceptor solvent, acetonitrile, to the benzene medium of the reactions of phenyl 2,4,6-trinitrophenyl ether with aniline and cyclohexylamine, respectively have been investigated. The addition produced similar effects in the two reactions—continuous rate increase with increasing amounts of acetonitrile. The results are interpreted in terms of the effect of amine–solvent interaction on the nucleophilicity of the amines and are in accord with our expectations based on the effects observed for hydrogen-bond donor solvent, methanol on the same reactions. It is also established from the results that the role of hydrogen-bond acceptor co-solvent could be played by an added more basic non-nucleophilic amine.
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