Proximity Effects on Nitrogen-15 Chemical Shifts of 8-Substituted 1-Nitronaphthalenes and 1-Naphthylamines

Abstract

^(15)N chemical shifts of several substituted 1-nitronaphthalenes and 8-substituted 1-naphthylamines have been determined and, in general, the substituent effects are unexpectedly small. The high-field shift of the amine nitrogen of 8-nitro-1-aminonaphthalene may indicate a degree of σ complexing between the amino group and the proximate substituents of the type suggested by Dunitz. The smallness of the other substituent effects may be the result of mutual cancellation of opposing larger effects.

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