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Noncovalent Lone Pair⋅⋅⋅(No‐π!)‐Heteroarene Interactions: The Janus‐Faced Hydroxy Group
Author(s) -
Pavlakos Ilias,
Arif Tanzeel,
Aliev Abil E.,
Motherwell William B.,
Tizzard Graham J.,
Coles Simon J.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201502103
Subject(s) - chemistry , lone pair , quinoxaline , hydrogen bond , ring (chemistry) , non covalent interactions , intramolecular force , janus , pyrazine , alkyl , benzene , stereochemistry , molecule , organic chemistry , nanotechnology , materials science
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.