Theoretical study on the mechanism of selective fluorination of aromatic compounds with Selectfluor

doi:10.1039/c4ra15202f

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	Theoretical study on the mechanism of selective fluorination of aromatic compounds with Selectfluor
	Geng, Cuihuan 1; Du, Likai2 ; Liu, Fang 1; Zhu, Rongxiu 1; Liu, Chengbu 1
	2015
发表期刊	RSC ADVANCES
卷号	5 期号:42 页码:33385-33391
摘要	The selective fluorination of aromatic compounds with Selectfluor has been studied theoretically. The structural and energetic features of pi complexes of substituted benzenes with Selectfluor are investigated, and the fluorine bond (F center dot center dot center dot pi) has been found to make an important contribution to the stabilization of the p complexes. Our calculations indicate that the SET mechanism, which involves one electron transfer from the aromatic substrate (D) to Selectfluor (A), is preferred over the S(N)2 mechanism. The analysis of the minimum energy path (MEP) suggests that the DABCO moiety of Selectfluor seems to take an active role in the fluorination of aromatic compounds with Selectfluor. In addition, a two-state model analysis, as well as the characteristics of avoiding crossing between the DA and D(+)A(-) states of benzene/Selectfluor are addressed to obtain deep insight into the features of the SET mechanism.
文章类型	Article
WOS标题词	Science & Technology ; Physical Sciences
DOI	10.1039/c4ra15202f
关键词[WOS]	SPHERE ELECTRON-TRANSFER ; NUCLEOPHILIC-SUBSTITUTION ; DENSITY FUNCTIONALS ; ORGANIC-CHEMISTRY ; F-TEDA-BF4 ; NITRATION ; REAGENTS ; SOLVENT ; ARENES ; STATES
收录类别	SCI
语种	英语
WOS研究方向	Chemistry
WOS类目	Chemistry, Multidisciplinary
WOS记录号	WOS:000353166700063
引用统计
文献类型	期刊论文
条目标识符	http://ir.qibebt.ac.cn/handle/337004/6449
专题	蛋白质设计研究组
作者单位	1.Shandong Univ, Sch Chem & Chem Engn, Inst Theoret Chem, Jinan 250100, Peoples R China 2.Chinese Acad Sci, Qingdao Inst Bioenergy & Bioproc Technol, Key Lab Biobased Mat, Qingdao 266101, Shandong, Peoples R China
推荐引用方式 GB/T 7714	Geng, Cuihuan,Du, Likai,Liu, Fang,et al. Theoretical study on the mechanism of selective fluorination of aromatic compounds with Selectfluor[J]. RSC ADVANCES,2015,5(42):33385-33391.
APA	Geng, Cuihuan,Du, Likai,Liu, Fang,Zhu, Rongxiu,&Liu, Chengbu.(2015).Theoretical study on the mechanism of selective fluorination of aromatic compounds with Selectfluor.RSC ADVANCES,5(42),33385-33391.
MLA	Geng, Cuihuan,et al."Theoretical study on the mechanism of selective fluorination of aromatic compounds with Selectfluor".RSC ADVANCES 5.42(2015):33385-33391.