Noncovalent Lone Pair⋅⋅⋅(No‐π!)‐Heteroarene Interactions: The Janus‐Faced Hydroxy Group1. Issue 28 (27th May 2015)

• Record Type: Journal Article
• Authors: Pavlakos, Ilias; Arif, Tanzeel; Aliev, Abil E.; Motherwell, William B.; Tizzard, Graham J.; Coles, Simon J.
• Is Part Of: Angewandte Chemie international edition. Volume 54:Issue 28(2015)
• Page Start: 8169
• Page End: 8174
• Publication Date: 2015-05-27
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201502103
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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.</p> </abstract>