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Substituted anilines: The tug-of-war between pyramidalization and resonance inside and outside of crystal cavities by Igor V. Alabugin; Mariappan Manoharan; Matthew Buck; Ronald J. Clark is a Chemistry article available to read on EtoBox.

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Efficient rehybridization at nitrogen provides a convenient conceptual framework for rationalizing structural and electronic effects in substituted anilines. Computations predict that a subtle balance between hybridization and conjugation in substituted anilines is easily perturbed by remote substitution. Rehybridization correlates with electronegativity of substituents as predicted by the Bent's rule even though the substitution is not direct but mediated by an aromatic system. Use of the r À Hammett parameters significantly improves the description of substituent effects. Limitations of X-ray crystallography in studies of subtle electronic structure effects are shown through comparison of computational geometries with crystallographic data which illustrates how supramolecular forces associated with the crystal packing mask intrinsic electronic preferences.

Who reads Substituted anilines: The tug-of-war between pyramidalization and resonance inside and outside of crystal cavities?

Author

Igor V. Alabugin; Mariappan Manoharan; Matthew Buck; Ronald J. Clark

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 0166-1280)

Published

2007

Language

EN

Field

Chemistry (Physical Sciences)