An ab initio study of the NMR properties (absolute shieldings and NICS) of a series of significant aromatic and antiaromatic compounds

被引：33

作者：

Alkorta, I ^{[1
]}

Rozas, I ^{[1
]}

Elguero, J ^{[1
]}

机构：

[1] CSIC, Inst Quim Med, E-28006 Madrid, Spain

来源：

TETRAHEDRON | 2001年 / 57卷 / 28期

关键词：

aromaticity; antiaromaticity; annulenes; GIAO; NICS;

D O I：

10.1016/S0040-4020(01)00585-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The absolute shieldings of protons and the nuclear independent chemical shifts of six aromatic and antiaromatic hydrocarbons have been calculated at the GIAO/B3LYP/6-31C* level. In general, the results are in agreement with the experiment ones except in the case of 1,5,9-tridehydro[1,2]annulene 7. Three possible explanations have been tested for this compound concluding that the anomaly (similar to 14 ppm!) probably lies on the use of a DFT approach. (C) 2001 Elsevier Science Ltd. All rights reserved.

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页码：6043 / 6049

页数：7

相关论文

共 63 条

[1]

ABRAHAM RJ, 2000, J CHEM SOC P2, P803

[2] Diaminocarbenes;: Calculation of barriers to rotation about Ccarbene-N bonds, barriers to dimerization, proton affinities, and 13C NMR shifts [J].

Alder, RW ;

Blake, ME ;

Oliva, JM .

JOURNAL OF PHYSICAL CHEMISTRY A, 1999, 103 (50) :11200-11211

[3] Ab initio hybrid DFT-GIAO calculations of the shielding produced by carbon-carbon bonds and aromatic rings in 1H NMR spectroscopy [J].

Alkorta, I ;

Elguero, J .

NEW JOURNAL OF CHEMISTRY, 1998, 22 (04) :381-385

[4] Ab initio (GIAO) calculations of absolute nuclear shieldings for representative compounds containing 1(2)H, 6(7)Li, 11B, 13C, 14(15)N, 17O, 19F, 29Si, 31P, 33S, and 35Cl nuclei [J].

Alkorta, I ;

Elguero, J .

STRUCTURAL CHEMISTRY, 1998, 9 (03) :187-202

[5] Calculation of the structure and nuclear magnetic shielding constants of some H-bonded carbon acid complexes [J].

Aminova, RM ;

Schamov, GA ;

Aganov, AV .

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2000, 498 :233-246

[6]

Balaban A. T., 1987, ANNULENES BENZOHETER, VI, p[92, 103]

[7] Theoretical study of tetramethyl- and tetra-tert-butyl-substituted cyclobutadiene and tetrahedrane [J].

Balci, M ;

McKee, ML ;

Schleyer, PV .

JOURNAL OF PHYSICAL CHEMISTRY A, 2000, 104 (06) :1246-1255

[8]

Bartolotti L.J., 1996, REV COMP CHEM, V7, P187, DOI [10.1002/9780470125847.ch4, DOI 10.1002/9780470125847.CH4]

[9] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[10] Aza[10]annulene: Next higher aromatic analogue of pyridine [J].

Bettinger, HF ;

Sulzbach, HM ;

Schleyer, PV ;

Schaefer, HF .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :3278-3280

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