Why [6,6]- and 1,2-Benzal-3-N-4-O-Cyclic Phenylimidate C-60 Undergo Electrochemically Induced Retro-Addition Reactions while 1,4-Dibenzyl-2,3-Cyclic Phenylimidate C-60 Does Not? C-H center dot center dot center dot X (X = N, O) Intramolecular Interactions in Organofullerenes

	Why [6,6]- and 1,2-Benzal-3-N-4-O-Cyclic Phenylimidate C-60 Undergo Electrochemically Induced Retro-Addition Reactions while 1,4-Dibenzyl-2,3-Cyclic Phenylimidate C-60 Does Not? C-H center dot center dot center dot X (X = N, O) Intramolecular Interactions in Organofullerenes
	Li FF ; Gao X ; Zheng M
刊名	journal of organic chemistry
	2009
卷号	74 期号:1 页码:82-87
关键词	POLYMER SOLAR-CELLS CRYSTAL-STRUCTURE HYDROGEN-BONDS CYCLOADDITION REACTION FULLERENE DERIVATIVES NEUTRON-DIFFRACTION BINGEL REACTION AB-INITIO CHEMISTRY PYRROLIDINOFULLERENES
ISSN号	0022-3263
通讯作者	gao x
中文摘要	the electrochemical properties of a series of structurally related fullerooxazoles, [6,6] cyclic phenylimidate c-60 (1), 1,2-benzal-3-n-4-o-cyclic phenylimidate c-60 (2), and 1,4-dibenzyl-2,3-cyclic phenylimidate c-60 (3), are described, and the spectroscopic characterizations of their anionic species are reported. the results show that compounds i and 2 undergo retro-cycloaddition reactions that lead to the formation of c-60 and c61hph, respectively, upon two-electron-transfer reduction. however, compound 3 demonstrates much more electrochemical stability as no retro-cycloaddition reaction occurs under similar conditions. natural bond orbital (nbo) calculations on charge distribution show there is no significant difference among the dianions of 1, 2, and 3, indicating that the electrochemical stability of 3 is unlikely to be caused by the charge distribution difference of the dianions of three compounds. examination on the crystal structure of compound 3 reveals close contacts of the c-h group with the heteroatoms (n and o) of cyclic phenylimidate, suggesting the existence of c-h center dot center dot center dot x (x = n, o) intramolecular hydrogen bonding among the addends, which is further confirmed by nbo analysis.
收录类别	SCI
语种	英语
WOS记录号	WOS:000262004000010
公开日期	2010-06-18
内容类型	期刊论文
源URL	[http://202.98.16.49/handle/322003/12655]
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	Li FF,Gao X,Zheng M. Why [6,6]- and 1,2-Benzal-3-N-4-O-Cyclic Phenylimidate C-60 Undergo Electrochemically Induced Retro-Addition Reactions while 1,4-Dibenzyl-2,3-Cyclic Phenylimidate C-60 Does Not? C-H center dot center dot center dot X (X = N, O) Intramolecular Interactions in Organofullerenes[J]. journal of organic chemistry,2009,74(1):82-87.
APA	Li FF,Gao X,&Zheng M.(2009).Why [6,6]- and 1,2-Benzal-3-N-4-O-Cyclic Phenylimidate C-60 Undergo Electrochemically Induced Retro-Addition Reactions while 1,4-Dibenzyl-2,3-Cyclic Phenylimidate C-60 Does Not? C-H center dot center dot center dot X (X = N, O) Intramolecular Interactions in Organofullerenes.journal of organic chemistry,74(1),82-87.
MLA	Li FF,et al."Why [6,6]- and 1,2-Benzal-3-N-4-O-Cyclic Phenylimidate C-60 Undergo Electrochemically Induced Retro-Addition Reactions while 1,4-Dibenzyl-2,3-Cyclic Phenylimidate C-60 Does Not? C-H center dot center dot center dot X (X = N, O) Intramolecular Interactions in Organofullerenes".journal of organic chemistry 74.1(2009):82-87.