Noncovalent Interactions of π Systems with Sulfur: The Atomic Chameleon of Molecular Recognition. Issue 5 (28th December 2017)

• Record Type: Journal Article
• Authors: Motherwell, William B.; Moreno, Rafael B.; Pavlakos, Ilias; Arendorf, Josephine R. T.; Arif, Tanzeel; Tizzard, Graham J.; Coles, Simon J.; Aliev, Abil E.
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 5(2018)
• Page Start: 1193
• Page End: 1198
• Publication Date: 2017-12-28
• Subjects: conformational analysis -- molecular balances -- NMR spectroscopy -- noncovalent interactions -- π-interactions; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201708485
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: The relative strength of noncovalent interactions between a thioether sulfur atom and various π systems in designed top pan molecular balances was determined by NMR spectroscopy. Compared to its oxygen counterpart, the sulfur atom displays a remarkable ability to interact with almost equal facility over the entire range of π systems studied, with the simple alkene emerging as the most powerful partner. With the exception of the O⋅⋅⋅heteroarene interaction, all noncovalent interactions of sulfur with π systems are favoured over oxygen. Abstract : Sulfur tips the balance : The relative strength of noncovalent interactions between a thioether sulfur atom and π systems in molecular balances was determined by NMR spectroscopy. The sulfur atom displays a remarkable ability to interact with almost equal facility over the entire range of π systems studied. With the exception of the O⋅⋅⋅heteroarene interaction, all noncovalent interactions of sulfur with π systems are favoured over oxygen.