Tipping the Balance between S-π and O-π Interactions

被引：49

作者：

Hwang, Jungwun ^{[1
]}

Li, Ping ^{[1
]}

Smith, Mark D. ^{[1
]}

Warden, Constance E. ^{[2
]}

Sirianni, Dominic A. ^{[2
]}

Vik, Erik C. ^{[1
]}

Maier, Josef M. ^{[1
]}

Yehl, Christopher J. ^{[1
]}

Sherrill, C. David ^{[2
,3
]}

Shimizu, Ken D. ^{[1
]}

机构：

[1] Univ South Carolina, Dept Chem & Biochem, Columbia, SC 29208 USA

[2] Georgia Inst Technol, Sch Chem & Biochem, Ctr Computat Mol Sci & Technol, Atlanta, GA 30332 USA

[3] Georgia Inst Technol, Sch Computat Sci & Engn, Atlanta, GA 30332 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2018年 / 140卷 / 41期

基金：

美国国家科学基金会;

关键词：

SIDE-CHAIN INTERACTIONS; AROMATIC STACKING INTERACTIONS; MOLECULAR TORSION BALANCES; CONTAINING AMINO-ACIDS; AB-INITIO; NONCOVALENT INTERACTIONS; PROTEIN STRUCTURES; ARENE INTERACTIONS; SOLID-STATE; SULFUR;

D O I：

10.1021/jacs.8b07617

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A comprehensive experimental survey consisting of 36 molecular balances was conducted to compare 18 pairs of S-pi versus O-pi interactions over a wide range of structural, geometric, and solvent parameters. A strong linear correlation was observed between the folding energies of the sulfur and oxygen balances across the entire library of balance pairs. The more stable interaction systematically switched from the O-pi to S-pi interaction. Computational studies of bimolecular PhSCH3-arene and PhOCH3-arene complexes were able to replicate the experimental trends in the molecular balances. The change in preference for the O-pi to S-pi interaction was due to the interplay of stabilizing (dispersion and solvophobic) and destabilizing (exchange-repulsion) terms arising from the differences in size and polarizability of the oxygen and sulfur atoms.

引用

页码：13301 / 13307

页数：7

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