Noncovalent Interactions of π Systems with Sulfur: The Atomic Chameleon of Molecular Recognition

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...

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Bibliographic Details
Published in:Angewandte Chemie 2018-01, Vol.130 (5), p.1207-1212
Main Authors: Motherwell, William B., Moreno, Rafael B., Pavlakos, Ilias, Arendorf, Josephine R. T., Arif, Tanzeel, Tizzard, Graham J., Coles, Simon J., Aliev, Abil E.
Format: Article
Language:eng ; ger
Subjects:
Alkenes
Chemical bonds
Chemistry
Konformationsanalyse
Magnetic resonance spectroscopy
Molekulare Waagen
Nichtkovalente Wechselwirkungen
NMR
NMR spectroscopy
NMR-Spektroskopie
Nuclear magnetic resonance
Oxygen
Sulfur
π-Wechselwirkungen
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Summary: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. Schwefel gibt den Ausschlag: Die relative Stärke der nichtkovalenten Wechselwirkungen zwischen einem Thioether‐Schwefelatom und π‐Systemen in molekularen Waagen wurde durch NMR‐Spektroskopie bestimmt. Das Schwefelatom wechselwirkt mit fast gleicher Stärke mit den untersuchten π‐Systemen, und mit Ausnahme der O⋅⋅⋅Heteroaren‐Wechselwirkung sind alle nichtkovalenten Wechselwirkungen von Schwefel mit π‐Systemen gegenüber Sauerstoff bevorzugt.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201708485