title: Noncovalent Lone Pair⋅⋅⋅(No-π!)-Heteroarene Interactions: The Janus-Faced Hydroxy Group.
abstract: A comparative study using NMR spectroscopy and designed top-pan molecular balances demonstrates that the noncovalent interaction of a hydroxy group with π-deficient pyrazine and quinoxaline units involves a lone pair-heteroarene interaction which is much stronger and solvent independent when measured relative to the classical π-facial hydrogen bond to a benzene ring. Alkyl fluorides also prefer the heteroarene rings over the benzene ring. The attractive interaction between a quinoxaline and a terminal alkyne is also stronger than the intramolecular hydrogen bond to an arene.
authors.affiliation: Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ (UK).
authors.forename: Ilias
authors.initials: I
authors.lastname: Pavlakos
authors.affiliation: Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ (UK).
authors.forename: Tanzeel
authors.initials: T
authors.lastname: Arif
authors.affiliation: Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ (UK). a.e.aliev@ucl.ac.uk.
authors.forename: Abil E
authors.initials: AE
authors.lastname: Aliev
authors.affiliation: Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ (UK). w.b.motherwell@ucl.ac.uk.
authors.forename: William B
authors.initials: WB
authors.lastname: Motherwell
authors.affiliation: School of Chemistry, University of Southampton, University Road, Southampton, SO17 1BJ (UK).
authors.forename: Graham J
authors.initials: GJ
authors.lastname: Tizzard
authors.affiliation: School of Chemistry, University of Southampton, University Road, Southampton, SO17 1BJ (UK).
authors.forename: Simon J
authors.initials: SJ
authors.lastname: Coles
mesh_terms: D000147:Acids, Heterocyclic / Q000737:chemistry*; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D008958:Models, Molecular
chemical_list: D000147:Acids, Heterocyclic
keywords: NMR spectroscopy; conformational analysis; heterocycles; noncovalent interactions; π interactions