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
收藏
页码：1320 / 1323
页数：4
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