Magnetic criteria of aromaticity in a benzene cation and anion: how does the Jahn-Teller effect influence the aromaticity?

被引：13

作者：

Andjelkovic, Ljubica ^{[1
]}

Peric, Marko ^{[1
]}

Zlatar, Matija ^{[1
]}

Grubisic, Sonja ^{[1
]}

Gruden-Pavlovic, Maja ^{[2
]}

机构：

[1] Univ Belgrade, IHTM, Ctr Chem, Belgrade 11001, Serbia

[2] Univ Fribourg, Dept Chem, CH-1700 Fribourg, Switzerland

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 07期

基金：

瑞士国家科学基金会;

关键词：

DFT; Aromaticity; Jahn-Teller effect; Intrinsic Distortion Path; INDEPENDENT CHEMICAL-SHIFTS; DENSITY; ELECTRON; NICS; DISTORTION; ENERGIES; ACCURATE; DFT;

D O I：

10.1016/j.tetlet.2011.12.008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The aromatic/antiaromatic behavior of the Jahn-Teller UT) active benzene cation and anion has been investigated using Density Functional Theory (DFT) calculations of Nuclear Independent Chemical Shifts (NICS) and magnetic susceptibility. NICS parameters have been scanned along the Intrinsic Distortion Path (IDP) for the benzene cation showing antiaromaticity which decreases with increasing deviation from D-6h to D-2h symmetry. Changes in NICS values along the IDP from D-6h to C-2v in the benzene anion revealed non-aromatic character. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：794 / 799

页数：6

共 36 条

[11] Induced magnetic fields in aromatic [n]-annulenes -: interpretation of NICS tensor components
Corminboeuf, C
Heine, T
Seifert, G
Schleyer, PV
Weber, J
[J]. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2004, 6 (02) : 273 - 276
[12] Conceptual and computational DFT in the study of aromaticity
De Proft, F
Geerlings, P
[J]. CHEMICAL REVIEWS, 2001, 101 (05) : 1451 - 1464
[13] Frisch M. J., 2016, Gaussian 03 Revision B.03
[14] Garrat P.J., 1986, Aromaticity
[15] Aromaticity and ring currents
Gomes, JANF
Mallion, RB
[J]. CHEMICAL REVIEWS, 2001, 101 (05) : 1349 - 1383
[16] Treatment of the Multimode Jahn-Teller Problem in Small Aromatic Radicals
Gruden-Pavlovic, Maja
Garcia-Fernandez, Pablo
Andjelkovic, Ljubica
Daul, Claude
Zlatar, Matija
[J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2011, 115 (39) : 10801 - 10813
[17] Towards an order-N DFT method
Guerra, CF
Snijders, JG
te Velde, G
Baerends, EJ
[J]. THEORETICAL CHEMISTRY ACCOUNTS, 1998, 99 (06) : 391 - 403
[18] Quantum contributions to the benzene problem.
Hueckel, Erich
[J]. ZEITSCHRIFT FUR PHYSIK, 1931, 72 (5-6): : 310 - 337
[19] Quantum contributions to the problem of aromatic and unsaturated compounds. 3
Hueckel, Erich
[J]. ZEITSCHRIFT FUR PHYSIK, 1932, 76 (9-10): : 628 - 648
[20] Analytic second derivatives of molecular energies: A density functional implementation
Jacobsen, H
Berces, A
Swerhone, DP
Ziegler, T
[J]. COMPUTER PHYSICS COMMUNICATIONS, 1997, 100 (03) : 263 - 276

← 1 2 3 4 →