Counterintuitive interaction of anions with benzene derivatives

被引：170

作者：

Quiñonero, D ^{[1
]}

Garau, C ^{[1
]}

Frontera, A ^{[1
]}

Ballester, P ^{[1
]}

Costa, A ^{[1
]}

Deyà, PM ^{[1
]}

机构：

[1] Univ Illes Balears, Dept Quim, E-07071 Palma de Mallorca, Spain

来源：

CHEMICAL PHYSICS LETTERS | 2002年 / 359卷 / 5-6期

关键词：

D O I：

10.1016/S0009-2614(02)00709-1

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Ab initio calculations were carried out on complexes between 1,3,5-trinitrobenzene (TNB) and anions, where the anion is positioned over the ring along the C-3 axis. This study combines crystallographic and computational evidences to demonstrate an attractive interaction between the anion and the pi-cloud of TNB. This interaction is rationalized based on the important role of the quadrupole moment of TNB and the anion-induced polarization. In addition, this study has been extended to 1,3,5-trifluorobenzene (TFB), which possesses a very small quadrupole moment. As a result, minimum energy complexes have been found between TFB and both anions and cations due to the stabilization obtained from the ion-induced polarization. (C) 2002 Elsevier Science B.V. All rights reserved.

引用

页码：486 / 492

页数：7

共 34 条

[1] 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

[2] Non-conventional hydrogen bonds [J].

Alkorta, I ;

Rozas, I ;

Elguero, J .

CHEMICAL SOCIETY REVIEWS, 1998, 27 (02) :163-170

[3] An attractive interaction between the pi-cloud of C6F6 and electron-donor atoms [J].

Alkorta, I ;

Rozas, I ;

Elguero, J .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) :4687-4691

[4] PROPERTIES OF ATOMS AND BONDS IN HYDROCARBON MOLECULES [J].

BADER, RFW ;

TANG, TH ;

TAL, Y ;

BIEGLERKONIG, FW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (04) :946-952

[5] ATOMS IN MOLECULES [J].

BADER, RFW .

ACCOUNTS OF CHEMICAL RESEARCH, 1985, 18 (01) :9-15

[6] ATOMIC CHARGES DERIVED FROM SEMIEMPIRICAL METHODS [J].

BESLER, BH ;

MERZ, KM ;

KOLLMAN, PA .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1990, 11 (04) :431-439

[7] 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-&

[8] THE MECHANICS OF HYDROGEN-BOND FORMATION IN CONJUGATED SYSTEMS [J].

CHEESEMAN, JR ;

CARROLL, MT ;

BADER, RFW .

CHEMICAL PHYSICS LETTERS, 1988, 143 (05) :450-458

[9] POLAR INTERACTIONS BETWEEN STACKED PI-SYSTEMS IN FLUORINATED 1,8-DIARYLNAPHTHALENES - IMPORTANCE OF QUADRUPOLE-MOMENTS IN MOLECULAR RECOGNITION [J].

COZZI, F ;

PONZINI, F ;

ANNUNZIATA, R ;

CINQUINI, M ;

SIEGEL, JS .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (09) :1019-1020

[10] A topological analysis of electron density in cation-π complexes [J].

Cubero, E ;

Orozco, M ;

Luque, FJ .

JOURNAL OF PHYSICAL CHEMISTRY A, 1999, 103 (02) :315-321

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