Corresponding Orbital Analysis of the Bonding of Some Monosubstituted Benzenes

A corresponding orbital analysis is used to study the nature of the interaction between the phenyl and substituent units of three monosubstituted benzenes; these are aniline, phenol, and fluorobenzene. The corresponding orbital eigenvalues clearly show significant trends in the σ symmetry charge donation from phenyl to substituent and the π Symmetry donation from substituent to phenyl. The F substituent accepts the largest amount of σ change from the ring but also donates the smallest amount of π charge to it. At the other extreme, NH3 is the poorest σ acceptor and the best π donor. © 1985, American Chemical Society. All rights reserved.