@article{discovery1466630, pages = {8169--8174}, publisher = {Wiley}, journal = {Angewandte Chemie International Edition}, number = {28}, note = {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{$\cdot$}{$\cdot$}{$\cdot$}(No-{\ensuremath{\pi}}!)-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.}, month = {July}, volume = {54}, title = {Noncovalent Lone Pair{$\cdot$}{$\cdot$}{$\cdot$}(No-{\ensuremath{\pi}}!)-Heteroarene Interactions: The Janus-Faced Hydroxy Group}, year = {2015}, abstract = {A comparative study by NMR using designed top pan molecular balances demonstrates that the noncovalent interaction of a hydroxyl group with {\ensuremath{\pi}}-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 {\ensuremath{\pi}}-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.}, url = {http://dx.doi.org/10.1002/anie.201502103}, issn = {1521-3757}, author = {Aliev, AE and Pavlakos, I and Arif, T and Aliev, AE and Motherwell, WB and Tizzard, GJ and Coles, SJ} }