%L discovery1466630 %I Wiley %N 28 %C Switzerland %J Angewandte Chemie International Edition %T Noncovalent Lone Pair⋅⋅⋅(No-π!)-Heteroarene Interactions: The Janus-Faced Hydroxy Group %A AE Aliev %A I Pavlakos %A T Arif %A AE Aliev %A WB Motherwell %A GJ Tizzard %A SJ Coles %X A comparative study by NMR using designed top pan molecular balances demonstrates that the noncovalent interaction of a hydroxyl group with π-deficient pyrazine and quinoxaline units involves a lone pair•••heteroarene interaction which is much stronger and essentially 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. %O This is the peer reviewed version of the following article: Aliev, AE; Pavlakos, I; Arif, T; Aliev, AE; Motherwell, WB; Tizzard, GJ; Coles, SJ; (2015) Noncovalent Lone Pair⋅⋅⋅(No-π!)-Heteroarene Interactions: The Janus-Faced Hydroxy Group. Angewandte Chemie International Edition , 54 (28) pp. 8169-8174. 10.1002/anie.201502103, which has been published in final form at http://dx.doi.org10.1002/anie.201502103. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. %D 2015 %P 8169-8174 %V 54