A new X-ray diffraction study of p-nitroaniline shows that through-conjugation has highly significant effects on the geometry of the molecule, as compared to aniline and p-nitrobenzoic acid. The effects include a moderate decrease of the internal angles of the ring at substituted carbons, with respect to values derived by superimposing independent angular distortions from each substituent.
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Colapietro et al. (1982) studied this question.
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