Theoretical investigation of ion pair S(N)2 reactions of alkali isothiocyanates with alkyl halides. Part 1. Reaction of lithium isothiocyanate and methyl fluoride with inversion mechanism
Zhu, HJ ; Ren, Y ; Ren, J ; Chu, SY
2005
发表期刊INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY
ISSN0020-7608
卷号101期号:1页码:104-112
摘要The gas-phase ionic S(N)2 reactions NCS- + CH3F and ion pair S(N)2 reaction LiNCS + CH3F with inversion mechanism were investigated at the level of MP2(full)/6-311+G**//HF/6-311+G**. Both of them involve the reactants complex, inversion transition state, and products complex. There are two possible reaction pathways in the ionic S(N)2 reaction but four reaction pathways in the ion pair S(N)2 reaction. Our results indicate that the introduction of lithium significantly lower the reaction barrier and make the ion pair displacement reaction more facile. For both ionic and ion pair reaction, methyl thiocyanate is predicted to be the major product, but the latter is more selective. More-stable methyl isothiocyanate can be prepared by thermal rearrangement of methyl thiocyanate. The theoretical predictions are consistent with the known experimental results. (C) 2004 Wiley Periodicals, Inc.
关键词Ab Initio Inversion Mechanism Isothiocyanate Reaction Pathway s(n)2 Thiocyanate Transition-state Structure Nucleophilic-substitution Reactions Retention Mechanisms Configuration
收录类别sci
语种英语
文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/15442
专题植物化学与西部植物资源持续利用国家重点实验室
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Zhu, HJ,Ren, Y,Ren, J,et al. Theoretical investigation of ion pair S(N)2 reactions of alkali isothiocyanates with alkyl halides. Part 1. Reaction of lithium isothiocyanate and methyl fluoride with inversion mechanism[J]. INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY,2005,101(1):104-112.
APA Zhu, HJ,Ren, Y,Ren, J,&Chu, SY.(2005).Theoretical investigation of ion pair S(N)2 reactions of alkali isothiocyanates with alkyl halides. Part 1. Reaction of lithium isothiocyanate and methyl fluoride with inversion mechanism.INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY,101(1),104-112.
MLA Zhu, HJ,et al."Theoretical investigation of ion pair S(N)2 reactions of alkali isothiocyanates with alkyl halides. Part 1. Reaction of lithium isothiocyanate and methyl fluoride with inversion mechanism".INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY 101.1(2005):104-112.
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