POLAR INTERACTIONS BETWEEN STACKED PI-SYSTEMS IN FLUORINATED 1,8-DIARYLNAPHTHALENES - IMPORTANCE OF QUADRUPOLE-MOMENTS IN MOLECULAR RECOGNITION

被引：286

作者：

COZZI, F ^{[1
]}

PONZINI, F ^{[1
]}

ANNUNZIATA, R ^{[1
]}

CINQUINI, M ^{[1
]}

SIEGEL, JS ^{[1
]}

机构：

[1] UNIV CALIF SAN DIEGO,DEPT CHEM & BIOCHEM,LA JOLLA,CA 92093

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1995年 / 34卷 / 09期

关键词：

FLUORINE COMPOUNDS; MOLECULAR RECOGNITION; STACKING INTERACTIONS;

D O I：

10.1002/anie.199510191

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

T‐shaped arrangements in the homodimers A and C of benzene and hexafluorobenzene, respectively, are rationalized by polar effects, but face‐to‐face stacking dominates in the 1:1 heterodimer B. The dynamics of a series of fluorinated 1,8‐diarylnaphthalenes clearly demonstrate the dependence of arene–arene interactions on the electronic characteristics of the arenes. The results are important for the design of supramolecular structures. (Figure Presented.) Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany

引用

页码：1019 / 1020

页数：2

共 48 条

[1]

ANNUNZIATA R, IN PRESS MAG RESON C

[2]

Battaglia M. R., 1981, Chemical Physics Letters, V78, P421, DOI 10.1016/0009-2614(81)85228-1

[3] RECOGNITION AND TRANSPORT OF ADENINE-DERIVATIVES WITH SYNTHETIC RECEPTORS [J].

BENZING, T ;

TJIVIKUA, T ;

WOLFE, J ;

REBEK, J .

SCIENCE, 1988, 242 (4876) :266-268

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

BURLEY, SK ;

PETSKO, GA .

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

[5] THROUGH-SPACE POLAR-PI EFFECTS ON THE ACIDITY AND HYDROGEN-BONDING CAPACITY OF CARBOXYLIC-ACIDS [J].

CHEN, CT ;

SIEGEL, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :5959-5960

[6]

CLAESSENS M, 1982, NOUV J CHIM, V6, P595

[7] PI-HYDROGEN BONDS AS A DESIGN PRINCIPAL IN MOLECULAR RECOGNITION [J].

COCHRAN, JE ;

PARROTT, TJ ;

WHITLOCK, BJ ;

WHITLOCK, HW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) :2269-2270

[8] POLAR/PI INTERACTIONS BETWEEN STACKED ARYLS IN 1,8-DIARYLNAPHTHALENES [J].

COZZI, F ;

CINQUINI, M ;

ANNUNZIATA, R ;

DWYER, T ;

SIEGEL, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5729-5733

[9] DOMINANCE OF POLAR/PI OVER CHARGE-TRANSFER EFFECTS IN STACKED PHENYL INTERACTIONS [J].

COZZI, F ;

CINQUINI, M ;

ANNUZIATA, R ;

SIEGEL, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) :5330-5331

[10] MOLECULAR-PACKING ANALYSIS OF MOLECULAR-COMPLEXES CONTAINING HEXAFLUOROBENZENE OR FLUORANIL [J].

DAHL, T .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1990, 46 :283-288

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