" Naked" hydrogencarbonate ion as a bifunctional catalyst toward amide substrates. Nucleophilic ion pairs. 9.

S Shinkai, N Nakashima, T Kunitake

Index: Shinkai, Seiji; Nakashima, Naotoshi; Kunitake, Toyoki Bulletin of the Chemical Society of Japan, 1981 , vol. 54, # 3 p. 840 - 845

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Abstract

The cleavage of amide substrates (p-nitro-N-methyltrifiuoroacetanilide and p-nitro-N- methyldichloroacetanilide) with anionic nucleophiles was studied at 30° C in aprotic (acetonitrile and N, N-dimethylformamide) and protic (ethanol) media. Hydrogencarbonate ion acted as catalyst much more efficiently in the aprotic solvents (about 10 3 fold) than expected from its aqueous pK a, but in ethanol, its reactivity was close to those of simple ...

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