Computational study of [10]annulene NMR spectra

被引：41

作者：

Price, DR

Stanton, JF ^{[1
]}

机构：

[1] Univ Texas, Dept Chem, Inst Theoret Chem, Austin, TX 78712 USA

[2] Univ Texas, Dept Biochem, Inst Theoret Chem, Austin, TX 78712 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 17期

关键词：

D O I：

10.1021/ol0200450

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] High-level theoretical methods are applied to calculate the C-13 NMR chemical shifts of three isomers of [10]annulene. Comparison with experiment clearly shows that the carrier of NMR signals of the so-called B form is the "twist" isomer. The results of this study strongly support predictions of relative energies of mono-trans [10]annulene isomers at the CCSD(T) level, which in turn are in qualitative disagreement with DFT and MP2 calculations.

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页码：2809 / 2811

页数：3

相关论文

共 17 条

[1] GAUSSIAN BASIS FUNCTIONS FOR USE IN MOLECULAR CALCULATIONS .1. CONTRACTION OF (9S5P) ATOMIC BASIS SETS FOR FIRST-ROW ATOMS [J].

DUNNING, TH .

JOURNAL OF CHEMICAL PHYSICS, 1970, 53 (07) :2823-+

[2] STRUCTURES AND STABILITIES OF ISOMERIC [10]ANNULENES [J].

FARNELL, L ;

KAO, J ;

RADOM, L ;

SCHAEFER, HF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (09) :2147-2151

[3] Perturbative treatment of triple excitations in coupled-cluster calculations of nuclear magnetic shielding constants [J].

Gauss, J ;

Stanton, JF .

JOURNAL OF CHEMICAL PHYSICS, 1996, 104 (07) :2574-2583

[4]

GAUSS J, IN PRESS ADV CHEM PH

[5] Conformations of [10]annulene: More bad news for density functional theory and second-order perturbation theory [J].

King, RA ;

Crawford, TD ;

Stanton, JF ;

Schaefer, HF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (46) :10788-10793

[6] [10] ANNULENES AND OTHER (CH)10 HYDROCARBONS [J].

MASAMUNE, S ;

DARBY, N .

ACCOUNTS OF CHEMICAL RESEARCH, 1972, 5 (08) :272-&

[7] (10)ANNULENES [J].

MASAMUNE, S ;

SEIDNER, RT .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (10) :542-&

[8] GEOMETRY OF (10]ANNULENES [J].

MASAMUNE, S ;

HOJO, K ;

BIGAM, G ;

RABENSTEIN, DL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (19) :4966-+

[9] AROMATICITY OF CONJUGATED MONOCYCLIC HYDROCARBONS [J].

MISLOW, K .

JOURNAL OF CHEMICAL PHYSICS, 1952, 20 (09) :1489-1490

[10] ACCURATE BINDING-ENERGIES OF DIBORANE, BORANE CARBONYL, AND BORAZANE DETERMINED BY MANY-BODY PERTURBATION-THEORY [J].

REDMON, LT ;

PURVIS, GD ;

BARTLETT, RJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (11) :2856-2862