title: H-bonding-assisted substituent effect.
abstract: In this paper we investigate the influence of intramolecular noncovalent interaction, i.e., H-bonding and Li-bonding, on the properties of substituents communicating through the resonance (mesomeric) effect in such molecular systems as salicylaldehyde, o-hydroxy Schiff base, o-nitrosophenol, and their lithium analogues. The investigated systems are usually considered as molecular patterns of intramolecular resonance-assisted hydrogen bonds (or its analogues in the case of Li-bonded systems). We show that the relation between intramolecular noncovalent interactions, A-H...B and A-Li...B, and the pi-electron delocalization in the sequence of pi-conjugated covalent bonds linking A and B can be considered in terms of the Hammett-like substituent effect in which electron-donating and electron-withdrawing properties of substituents are affected by the noncovalent interaction.
authors.affiliation: Department of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland. tmkryg@chem.uw.edu.pl
authors.forename: Tadeusz M
authors.initials: TM
authors.lastname: Krygowski
authors.forename: Joanna E
authors.initials: JE
authors.lastname: Zachara-Horeglad
authors.forename: Marcin
authors.initials: M
authors.lastname: Palusiak
mesh_terms: D006859:Hydrogen / Q000737:chemistry*; D006860:Hydrogen Bonding; D008094:Lithium / Q000737:chemistry*
chemical_list: D006859:Hydrogen; D008094:Lithium