A theoretical study of the carbenoids LiCH2X (X = Cl, Br, I) cyclopropanation reaction with ketene

doi:10.1007/s12039-010-0041-8

	A theoretical study of the carbenoids LiCH2X (X = Cl, Br, I) cyclopropanation reaction with ketene
	Zhang, Xing Hui 1; Zhang, Fu Long 1; Geng, Zhi Yuan 2
	2010-05
发表期刊	JOURNAL OF CHEMICAL SCIENCES
ISSN	0974-3626
卷号	122 期号:3 页码:363-369
摘要	A computational study for the [2 + 1] addition of the lithium carbenoids LiCH2X (X = Cl, Br, I) with ketene have been investigated by means of the B3LYP hybrid density functional method. All the reactions examined displayed similar concerted mechanisms for the cyclopropanation of these reagents. The lithium carbenoids react with ketene via an asynchronous attack on one CH2 or C group of ketene with relatively low barrier to reaction in the range of 25.34-33.74 kJ/mol in THF solvent. The trend of the lithium carbenoids reaction barrier with ketene is LiCH2Cl < LiCH2Br < LiCH2I. The results show that the reactions could be highly chemical reactivity with low barriers and could be favoured in experiment. The reactions could proceed easily at lower temperature. The computational results are briefly compared to other carbenoid reactions and related species.
关键词	Density functional theory ketene lithium carbenoid Bromine compounds Chlorine compounds Computation theory Lithium Lithium compounds Organic solvents Carbenoid reaction Carbenoids Computational results Computational studies Concerted mechanism Cyclopropanation reaction Hybrid density functional method Ketene
DOI	10.1007/s12039-010-0041-8
收录类别	SCIE ; EI
语种	英语
WOS研究方向	Chemistry
WOS类目	Chemistry, Multidisciplinary
WOS记录号	WOS:000278596900007
出版者	INDIAN ACAD SCIENCES
EI入藏号	20102212962820
EI主题词	Iodine compounds
EI分类号	542.4 Lithium and Alloys ; 721.1 Computer Theory, Includes Formal Logic, Automata Theory, Switching Theory, Programming Theory ; 803 Chemical Agents and Basic Industrial Chemicals ; 922.1 Probability Theory
原始文献类型	Journal article (JA)
引用统计	被引频次：3[WOS] [WOS记录] [WOS相关记录]
文献类型	期刊论文
条目标识符	https://ir.nwnu.edu.cn/handle/39RV6HYL/36655
专题	实体学院_化学化工学院_化工系
通讯作者	Zhang, Xing Hui
作者单位	1.Gansu Lianhe Univ, Coll Chem Engn, Lanzhou 730010, Peoples R China; 2.NW Normal Univ, Coll Chem & Chem Engn, Lanzhou 730070, Peoples R China
推荐引用方式 GB/T 7714	Zhang, Xing Hui,Zhang, Fu Long,Geng, Zhi Yuan. A theoretical study of the carbenoids LiCH2X (X = Cl, Br, I) cyclopropanation reaction with ketene[J]. JOURNAL OF CHEMICAL SCIENCES,2010,122(3):363-369.
APA	Zhang, Xing Hui,Zhang, Fu Long,&Geng, Zhi Yuan.(2010).A theoretical study of the carbenoids LiCH2X (X = Cl, Br, I) cyclopropanation reaction with ketene.JOURNAL OF CHEMICAL SCIENCES,122(3),363-369.
MLA	Zhang, Xing Hui,et al."A theoretical study of the carbenoids LiCH2X (X = Cl, Br, I) cyclopropanation reaction with ketene".JOURNAL OF CHEMICAL SCIENCES 122.3(2010):363-369.

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