Electronic vs Steric Effects on the Stability of Anionic Species: A Case Study on the Ortho and Para Regioisomers of Organofullerenes

	Electronic vs Steric Effects on the Stability of Anionic Species: A Case Study on the Ortho and Para Regioisomers of Organofullerenes
	Chang,Wei-Wei; Li,Zong-Jun; He,Fa-Gui; Sun,Tao; Gao,Xiang
刊名	journal of organic chemistry
	2015
卷号	80 期号:3 页码:1557-1563
关键词	REDUCTIVE BENZYLATION BULKY ADDEND C-60 C-70 DERIVATIVES FULLERENES CHEMISTRY ELECTROCHEMISTRY ELECTROSYNTHESIS IMIDAZOLINE
通讯作者	gao,x
英文摘要	the stability of the anionic species of the ortho and para regioisomers of (meo)bnc(2)n (me = methyl, bn = benzyl, n = 30 or 35) has been examined. the results show that the ortho adducts (electronically favored regioisomers) are stable upon receiving one or two electrons, while the para ones (sterically favored adducts) decompose by removing the methoxy group under similar conditions. computational calculations indicate that the stability of the anionic species is significantly affected by the electronic structure, where the [5,6]-double bond is responsible for the instability of the reduced species of the para adducts. further study with 1,15-(meo)(2)-2,4-bn2c60, an adduct with both the ortho and para positioned methoxy, shows that the reduced species is stable, indicating that the 1,2,4,15-configuration is an electronically preferential structure even though it has a [5,6]-double bond.
收录类别	SCI
语种	英语
WOS记录号	WOS:000349934600027
公开日期	2016-05-31
内容类型	期刊论文
源URL	[http://ir.ciac.jl.cn/handle/322003/65088]
专题	长春应用化学研究所_长春应用化学研究所知识产出_期刊论文
推荐引用方式 GB/T 7714	Chang,Wei-Wei,Li,Zong-Jun,He,Fa-Gui,et al. Electronic vs Steric Effects on the Stability of Anionic Species: A Case Study on the Ortho and Para Regioisomers of Organofullerenes[J]. journal of organic chemistry,2015,80(3):1557-1563.
APA	Chang,Wei-Wei,Li,Zong-Jun,He,Fa-Gui,Sun,Tao,&Gao,Xiang.(2015).Electronic vs Steric Effects on the Stability of Anionic Species: A Case Study on the Ortho and Para Regioisomers of Organofullerenes.journal of organic chemistry,80(3),1557-1563.
MLA	Chang,Wei-Wei,et al."Electronic vs Steric Effects on the Stability of Anionic Species: A Case Study on the Ortho and Para Regioisomers of Organofullerenes".journal of organic chemistry 80.3(2015):1557-1563.