Binding features of molecular clips. Separation of the effects of hydrogen bonding and pi-pi interactions

被引：126

作者：

Reek, JNH ^{[1
]}

Priem, AH ^{[1
]}

Engelkamp, H ^{[1
]}

Rowan, AE ^{[1
]}

Elemans, JAAW ^{[1
]}

Nolte, RJM ^{[1
]}

机构：

[1] UNIV NIJMEGEN,NSR CTR,DEPT ORGAN CHEM,NL-6525 ED NIJMEGEN,NETHERLANDS

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1997年 / 119卷 / 42期

关键词：

D O I：

10.1021/ja970805f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The ability of clip shaped molecules based on the building block diphenylglycoluril to form complexes with dihydroxybenzene guest molecules has been studied in detail. The binding strength of these complexes can be varied over a wide range (K-a approximate to 0-10(5) M-1), by applying small modifications in the host or the guest molecule. It is found that the complexation is a combination of different effects, viz., hydrogen bonding, pi-pi stacking interactions, and a cavity effect.

引用

页码：9956 / 9964

页数：9

共 63 条

[1] SCALES OF SOLUTE HYDROGEN-BONDING - THEIR CONSTRUCTION AND APPLICATION TO PHYSICOCHEMICAL AND BIOCHEMICAL PROCESSES [J].

ABRAHAM, MH .

CHEMICAL SOCIETY REVIEWS, 1993, 22 (02) :73-83

[2] HYDROGEN-BONDING .9. SOLUTE PROTON DONOR AND PROTON ACCEPTOR SCALES FOR USE IN DRUG DESIGN [J].

ABRAHAM, MH ;

DUCE, PP ;

PRIOR, DV ;

BARRATT, DG ;

MORRIS, JJ ;

TAYLOR, PJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (10) :1355-1375

[3] HYDROGEN-BONDING .7. A SCALE OF SOLUTE HYDROGEN-BOND ACIDITY BASED ON LOG K-VALUES FOR COMPLEXATION IN TETRACHLOROMETHANE [J].

ABRAHAM, MH ;

GRELLIER, PL ;

PRIOR, DV ;

DUCE, PP ;

MORRIS, JJ ;

TAYLOR, PJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (06) :699-711

[4] Chemical double-mutant cycles for the measurement of weak intermolecular interactions: Edge-to-face aromatic interactions [J].

Adams, H ;

Carver, FJ ;

Hunter, CA ;

Morales, JC ;

Seward, EM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (13-14) :1542-1544

[5] CHEMISTRY OF SYNTHETIC RECEPTORS AND FUNCTIONAL-GROUP ARRAYS .15. EFFECTS OF ADDED WATER ON THERMODYNAMIC ASPECTS OF HYDROGEN-BOND-BASED MOLECULAR RECOGNITION IN CHLOROFORM [J].

ADRIAN, JC ;

WILCOX, CS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :678-680

[6]

[Anonymous], 1988, ANGEW CHEM, V100, P1041, DOI DOI 10.1002/ANGE.19881000804

[7] HEXAGONAL LATTICE HOSTS FOR UREA - A NEW SERIES OF DESIGNED HETEROCYCLIC RECEPTORS [J].

BELL, TW ;

LIU, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3673-3674

[8] ORIGIN OF THE STRONG BINDING OF ADENINE TO A MOLECULAR TWEEZER [J].

BLAKE, JF ;

JORGENSEN, WL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (20) :7269-7278

[9]

BRIEGLEB G, 1991, ELECTRONEN DONATOR A

[10] AROMATIC-AROMATIC INTERACTION - A MECHANISM OF PROTEIN-STRUCTURE STABILIZATION [J].

BURLEY, SK ;

PETSKO, GA .

SCIENCE, 1985, 229 (4708) :23-28

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