Why Are Some (CH)4X6 and (CH2)6X4 Polyheteroadamantanes So Stable?

被引：16

作者：

Wang, Yan ^{[1
,2
]}

Wu, Judy I-Chia ^{[2
]}

Li, Qianshu ^{[1
]}

Schleyer, Paul von Rague ^{[2
]}

机构：

[1] Beijing Inst Technol, Sch Sci, Beijing 100081, Peoples R China

[2] Univ Georgia, Dept Chem, Ctr Computat Chem, Athens, GA 30602 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 06期

基金：

美国国家科学基金会;

关键词：

X-RAY-STRUCTURE; NEGATIVE HYPERCONJUGATION; MOLECULAR-PROPERTIES; ADDITIVITY; ENERGIES; DELOCALIZATION; ADAMANTANE; CARBON; THERMOCHEMISTRY; AROMATICITY;

D O I：

10.1021/ol1002187

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The representative isodesmic reactions shown in the Abstract graphic for (CH)(4)X-6 hexaheteroadamantane derivatives reveal energetic nonadditivity to remarkably different extents: while the electropositive element stabilizations are exceptionally large and the pnictide and hexaoxaadamantane stabilizations are more modest, the sulfur and selenium analogues are destabilized. Similar behavior Is exhibited by (CH2)(6)X-4 tetraheteroadamantanes. Analysis shows that aromaticity is not involved; the sign and magnitude of the nonadditivity depends on the Interplay of hyperconjugation, electrostatic, and steric (lone pair repulsion) effects.

引用

页码：1320 / 1323

页数：4

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