Journal of the Chemical Society. Perkin transactions II p. 217 - 222 (1984)
Update date:2022-08-03
Topics:
Beach, Steven F.
Hepworth, John D.
Sawyer, John
Hallas, Geoffrey
Marsden, Richard
et al.
Apparent dipole moments in benzene of various p-substituted N-phenyl derivatives of pyrrolidine, piperidine, morpholine, and thiomorpholine and of some analogous NN-diethylanilines have been determined.Vector moments along the bisector of angle CH2NCH2 and also in the direction of the major axis of the aromatic ring have been calculated for the parent compounds.The order of magnitude of the latter is N-phenylpyrrolidine>NN-diethylaniline>N-phenylpiperidine>N-phenylmorpholine>N-phenylthiomorpholine.The nature of the heterocycle does not greatly affect the additional moment, μ(add.), along the major axis of the aromatic ring, required to account for the moments of the p-substituted compounds.In each series of compounds, μ(add.) parallels the Hammett substituent constant, ?.
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