Why downfield proton chemical shifts are not reliable aromaticity indicators

被引：78

作者：

Faglioni, F

Ligabue, A

Pelloni, S

Soncini, A

Viglione, RG

Ferraro, MB

Zanasi, R

Lazzeretti, P

机构：

[1] Univ Modena, Dipartimento Chim, I-41100 Modena, Italy

[2] Univ Salerno, Dipartimento Chim, I-84081 Baronissi, Italy

[3] Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Fis, RA-1428 Buenos Aires, DF, Argentina

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 16期

关键词：

D O I：

10.1021/ol051103v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Traces of magnetizability, traces of magnetic shielding at the hydrogen nuclei, and nucleus-independent chemical shift are not reliable aromaticity quantifiers for planar conjugated hydrocarbons. A measure of aromaticity is provided by the out-of-plane tensor components, whose magnitude is influenced by the pi-ring currents. The failure of nucleus-independent chemical shift in this regard was proved for the molecule shown in the abstract graphic, sustaining a diatropic pi-current. The validity of the ring-current model is reaffirmed.

引用

页码：3457 / 3460

页数：4

共 24 条

[1] The ring-current model of the paratropic pentalene molecule [J].