How strong is a pi-facial hydrogen bond?

被引：67

作者：

Adams, H

Harris, KDM

Hembury, GA

Hunter, CA

Livingstone, D

McCabe, JF

机构：

[1] UNIV BIRMINGHAM,SCH CHEM,BIRMINGHAM B15 2TT,W MIDLANDS,ENGLAND

[2] SMITHKLINE BEECHAM,WELWYN GARDEN CIT AL6 9AR,HERTS,ENGLAND

来源：

CHEMICAL COMMUNICATIONS | 1996年 / 22期

关键词：

D O I：

10.1039/cc9960002531

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Functional group substitutions (chemical mutations) in a molecular zipper complex have been used to construct a thermodynamic cycle for estimating the strength of a pi-facial H-bond between an NH group and an aromatic ring resulting in a lower limit of -4.5 +/- 0.5 kJ mol(-1) for the magnitude of the intermolecular NH-pi interaction in chloroform.

引用

页码：2531 / 2532

页数：2

共 12 条

[1] Chemical double-mutant cycles for the measurement of weak intermolecular interactions: Edge-to-face aromatic interactions
Adams, H
Carver, FJ
Hunter, CA
Morales, JC
Seward, EM
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (13-14): : 1542 - 1544
[2] ADAMS H, 1996, CHEM COMMUN
[3] MOLECULAR RECOGNITION .2. MOLECULAR RECOGNITION OF AMINO-ACIDS - 2-POINT FIXATION OF AMINO-ACIDS WITH BIFUNCTIONAL METALLOPORPHYRIN RECEPTORS
AOYAMA, Y
YAMAGISHI, A
ASAGAWA, M
TOI, H
OGOSHI, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (12) : 4076 - 4077
[4] HYDROGEN-BONDING AND MOLECULAR RECOGNITION - SYNTHETIC, COMPLEXATION, AND STRUCTURAL STUDIES ON BARBITURATE BINDING TO AN ARTIFICIAL RECEPTOR
CHANG, SK
VANENGEN, D
FAN, E
HAMILTON, AD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) : 7640 - 7645
[5] FONG TM, 1993, NATURE, V362, P350
[6] STRUCTURAL CONSEQUENCES OF A MOLECULAR ASSEMBLY THAT IS DEFICIENT IN HYDROGEN-BOND ACCEPTORS
HANTON, LR
HUNTER, CA
PURVIS, DH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (16) : 1134 - 1136
[7] Hunter C. A., 1994, CHEM SOC REV, P101
[8] AROMATIC RINGS ACT AS HYDROGEN-BOND ACCEPTORS
LEVITT, M
PERUTZ, MF
[J]. JOURNAL OF MOLECULAR BIOLOGY, 1988, 201 (04) : 751 - 754
[9] DECOMPOSITION OF THE FREE-ENERGY OF A SYSTEM IN TERMS OF SPECIFIC INTERACTIONS - IMPLICATIONS FOR THEORETICAL AND EXPERIMENTAL STUDIES
MARK, AE
VANGUNSTEREN, WF
[J]. JOURNAL OF MOLECULAR BIOLOGY, 1994, 240 (02) : 167 - 176
[10] AMINO AROMATIC INTERACTIONS
MITCHELL, JBO
NANDI, CL
ALI, S
MCDONALD, JK
THORNTON, JM
PRICE, SL
SINGH, J
[J]. NATURE, 1993, 366 (6454) : 413 - 413

← 1 2 →