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

被引:42
|
作者
Motherwell, William B. [1 ]
Moreno, Rafael B. [1 ]
Pavlakos, Ilias [1 ]
Arendorf, Josephine R. T. [1 ]
Arif, Tanzeel [1 ]
Tizzard, Graham J. [2 ]
Coles, Simon J. [2 ]
Aliev, Abil E. [1 ]
机构
[1] UCL, Dept Chem, 20 Gordon St, London WC1H 0AJ, England
[2] Univ Southampton, Sch Chem, Univ Rd, Southampton SO17 1BJ, Hants, England
基金
英国工程与自然科学研究理事会;
关键词
conformational analysis; molecular balances; NMR spectroscopy; noncovalent interactions; pi-interactions; AROMATIC INTERACTIONS; ARENE INTERACTIONS; LONE-PAIR; DISPERSION; CHEMISTRY; RINGS; ACCURACY; BALANCES; DESIGN; FORCES;
D O I
10.1002/anie.201708485
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The relative strength of noncovalent interactions between a thioether sulfur atom and various pi 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 pi systems studied, with the simple alkene emerging as the most powerful partner. With the exception of the O center dot center dot center dot heteroarene interaction, all noncovalent interactions of sulfur with pi systems are favoured over oxygen.
引用
收藏
页码:1193 / 1198
页数:6
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