Weak C-H/π interaction participates in the diastereoselectivity of a host-guest complex in the presence of six strong hydrogen bonds

被引：33

作者：

Frontera, A ^{[1
]}

Garau, C ^{[1
]}

Quiñonero, D ^{[1
]}

Ballester, P ^{[1
]}

Costa, A ^{[1
]}

Deyà, PM ^{[1
]}

机构：

[1] Univ Illes Balears, Dept Quim, Palma de Mallorca 07122, Spain

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 07期

关键词：

D O I：

10.1021/ol034247n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] We report a study of the interaction between methylmethanetriacetic acid (MMTA) and a tripodal amidopyridine receptor 1, where the geometry of the binding is in part governed by a weak C-H/pi interaction in the presence of six strong N(O)-H...O(N) hydrogen bonds. There are two possible binding geometries for the 1:1 complex 1.MMTA; combining computational and experimental evidence we demonstrate that the endo binding mode is more favorable as the result of a C-H/pi interaction.

引用

页码：1135 / 1138

页数：4

共 23 条

[1]

ALDER WA, 1996, CHEM REV, V96, P2111

[2] Hydrogen-bond recognition of cyclic dipeptides in water [J].

Allott, C ;

Adams, H ;

Bernad, PL ;

Hunter, CA ;

Rotger, C ;

Thomas, JA .

CHEMICAL COMMUNICATIONS, 1998, (22) :2449-2450

[3] Oligocatenanes made to order [J].

Amabilino, DB ;

Ashton, PR ;

Balzani, V ;

Boyd, SE ;

Credi, A ;

Lee, JY ;

Menzer, S ;

Stoddart, JF ;

Venturi, M ;

Williams, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) :4295-4307

[4] Dual binding mode of methylmethanetriacetic acid to tripodal amidopyridine receptors [J].

Ballester, P ;

Capó, M ;

Costa, A ;

Deyà, PM ;

Gomila, R ;

Decken, A ;

Deslongchamps, G .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :8832-8841

[5] CALCULATION OF SMALL MOLECULAR INTERACTIONS BY DIFFERENCES OF SEPARATE TOTAL ENERGIES - SOME PROCEDURES WITH REDUCED ERRORS [J].

BOYS, SF ;

BERNARDI, F .

MOLECULAR PHYSICS, 1970, 19 (04) :553-&

[6] Is polarization important in cation-π interactions? [J].

Cubero, E ;

Luque, FJ ;

Orozco, M .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (11) :5976-5980

[7] POLARIZATION CORRECTIONS TO ELECTROSTATIC POTENTIALS [J].

FRANCL, MM .

JOURNAL OF PHYSICAL CHEMISTRY, 1985, 89 (03) :428-433

[8]

Frisch M.J., 2016, Gaussian 16 Revision C. 01. 2016, V16, P01

[9]

Hirota Y, 1998, C H PIE INTERACTION

[10]

KODAMA Y, 1977, TETRAHEDRON LETT, P2105

← 1 2 3 →