title: Reciprocal hydrogen bonding-aromaticity relationships.
abstract: Computed association energies and dissected nucleus-independent chemical shifts (NICS) document the mutual enhancement (or reduction) of intermolecular interactions and the aromaticity of H-bonded substrates. H-bonding interactions that increase cyclic 4n + 2 π-electron delocalization boost aromaticity. Conversely, such interactions are weakened when aromaticity is decreased as a result of more localized quinoidal π character. Representative examples of the tautomeric equilibria of π-conjugated heterocyclic compounds in protic solvents and other H-bonding environments also illustrate such H-bonding/aromaticity interplay.
authors.affiliation: Center for Computational Quantum Chemistry, University of Georgia , Athens, Georgia 30602, United States.
authors.forename: Judy I
authors.initials: JI
authors.lastname: Wu
authors.forename: James E
authors.initials: JE
authors.lastname: Jackson
authors.forename: Paul von Ragué
authors.initials: Pv
authors.lastname: Schleyer