4n π Electrons but Stable: N,N-Dihydrodiazapentacenes

被引：71

作者：

Wu, Judy I. ^{[1
]}

Wannere, Chaitanya S. ^{[1
]}

Mo, Yirong ^{[2
]}

Schleyer, Paul von Rague ^{[1
]}

Bunz, Uwe H. F. ^{[3
]}

机构：

[1] Univ Georgia, Dept Chem, Athens, GA 30602 USA

[2] Western Michigan Univ, Dept Chem, Kalamazoo, MI 49008 USA

[3] Georgia Inst Technol, Sch Chem & Biochem, Atlanta, GA 30332 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 11期

基金：

美国国家科学基金会;

关键词：

THIN-FILM TRANSISTORS; CHEMICAL-SHIFTS; RING CURRENTS; PENTACENE; AROMATICITY; MODEL; DERIVATIVES; BOND; NICS; HYPERCONJUGATION;

D O I：

10.1021/jo900684c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Despite having 4n pi electrons, dihydrodiazapentacenes are more viable than their 4n+2 pi azapentacene counterparts. Ab inito valence bond block-localized wave funtion (BLW) computations reveal that despite having 4 pi electrons, dihydrodiazapentacenes are stabilized and benefit substantially from four dihydropyrazine ethenamine (enamine) conjugations. Almost all of these dihydrodiazapentacenes have large negative overall nucleus independent chemical shifts NICS(0)(pi zz) values even though their dihydropyrazine rings (e.g., for 6-H-2) are modestly antiaromatic, as their paratropic contributions are attenuated by delocalization throughout the system.

引用

页码：4343 / 4349

页数：7

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