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

共 62 条

[1] Benzene-Hydrogen Bond (C6H6-HX) Interactions: The Influence of the X Nature on their Strength and Anisotropy [J].

Alberti, M. ;

Aguilar, A. ;

Huarte-Larranaga, F. ;

Lucas, J. M. ;

Pirani, F. .

JOURNAL OF PHYSICAL CHEMISTRY A, 2014, 118 (09) :1651-1662

[2] Sulphur Atoms from Methionines Interacting with Aromatic Residues Are Less Prone to Oxidation [J].

Aledo, Juan C. ;

Canton, Francisco R. ;

Veredas, Francisco J. .

SCIENTIFIC REPORTS, 2015, 5

[3] Ab initio study of substituent effects in the interactions of dimethyl ether with aromatic rings [J].

Amicangelo, Jay C. ;

Gung, Benjamin W. ;

Irwin, Daniel G. ;

Romano, Natalie C. .

PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2008, 10 (19) :2695-2705

[4] The Intramolecular Interaction of Thiophene and Furan with Aromatic and Fluoroaromatic Systems in Some [3.3]Meta(heterocyclo)paracyclophanes: A Combined Computational and NMR Spectroscopic Study [J].

Benaglia, Maurizio ;

Cozzi, Franco ;

Mancinelli, Michele ;

Mazzanti, Andrea .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (25) :7456-7468

[5] A Survey of the Role of Noncovalent Sulfur Interactions in Drug Design [J].

Beno, Brett R. ;

Yeung, Kap-Sun ;

Bartberger, Michael D. ;

Pennington, Lewis D. ;

Meanwell, Nicholas A. .

JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (11) :4383-4438

[6] Disulfide bonds, their stereospecific environment and conservation in protein structures [J].

Bhattacharyya, R ;

Pal, D ;

Chakrabarti, P .

PROTEIN ENGINEERING DESIGN & SELECTION, 2004, 17 (11) :795-808

[7] Effect of Diazocine Bridgehead Modification on the Folding of the Wilcox Molecular Torsion Balance: A View from a Different Angle [J].

Bhayana, Brijesh ;

Ams, Mark R. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (09) :3594-3596

[8] Sulfur, Not Too Far Behind O, N, and C: SH•••π Hydrogen Bond [J].

Biswal, Himansu S. ;

Wategaonkar, Sanjay .

JOURNAL OF PHYSICAL CHEMISTRY A, 2009, 113 (46) :12774-12782

[9] Modulation of flavin recognition and redox properties through donor atom-π interactions [J].

Breinlinger, EC ;

Keenan, CJ ;

Rotello, VM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (34) :8606-8609

[10] Characteristics of the interaction of azulene with water and hydrogen sulfide:: A computational study [J].

Cabaleiro-Lago, Enrique M. ;

Rodriguez-Otero, Jesus ;

Pena-Gallego, Angeles .

JOURNAL OF CHEMICAL PHYSICS, 2008, 129 (08)

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