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

[21] The magnitude of the CH/π interaction between benzene and some model hydrocarbons [J].

Tsuzuki, S ;

Honda, K ;

Uchimaru, T ;

Mikami, M ;

Tanabe, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (15) :3746-3753

[22] CH/π interaction in the conformation of organic compounds.: A database study [J].

Umezawa, Y ;

Tsuboyama, S ;

Takahashi, H ;

Uzawa, J ;

Nishio, M .

TETRAHEDRON, 1999, 55 (33) :10047-10056

[23] A NOVEL CALCIUM-BINDING SITE IN THE GALACTOSE-BINDING PROTEIN OF BACTERIAL TRANSPORT AND CHEMOTAXIS [J].

VYAS, NK ;

VYAS, MN ;

QUIOCHO, FA .

NATURE, 1987, 327 (6123) :635-638

← 1 2 3 →