Reference : A VARIABLE MECHANISM FOR THE NUCLEOPHILIC VINYLIC SUBSTITUTIONS IN A SERIES OF GEM-DI...
Scientific journals : Article
Physical, chemical, mathematical & earth Sciences : Chemistry
http://hdl.handle.net/2268/3985
A VARIABLE MECHANISM FOR THE NUCLEOPHILIC VINYLIC SUBSTITUTIONS IN A SERIES OF GEM-DIHALOGENATED ALKENES BY A BIDENTATE SULFUR NUCLEOPHILE - AN EXPERIMENTAL AND AM1 THEORETICAL-STUDY
English
Gimbert, Yves [ > > ]
Moradpour, Alec [ > > ]
Dive, Georges mailto [Université de Liège - ULg > > Centre d'ingénierie des protéines >]
Dehareng, Dominique mailto [Université de Liège - ULg > > Centre d'ingénierie des protéines >]
Lahlil, Khalid [ > > ]
1993
Journal of Organic Chemistry
American Chemical Society
58
17
4685-4690
Yes (verified by ORBi)
International
0022-3263
1520-6904
Columbus
OH
[en] gem-dihalogenated alkenes ; nucleophilic substitution ; ab initio calculations
[en] The nucleophilic substitutions of a series of gem-dihalogenated alkenes 3,5,7,8, and 9 (RS)2C=CX2 (X = Cl, F) with 1,2-benzenedithiolate b have been studied. Depending on the structures of the R groups (alkyl, saturated and unsaturated cycloalkyls, aromatic ring), the course of the reactions and the structures of the yielded products are modified. In the frame of the addition-elimination-type mechanism for these nucleophilic substitutions, the energy contents of the anionic intermediates, resulting from the additions of the nucleophile b to the unsaturated centers, is calculated at the AM1 method level. For the compounds 5, 7, 8, and 9, the calculated energies nicely corroborate the experimental results. For 3, anionic intermediates are no longer found by calculation, and a synchronous single-step substitution is strongly suggested.
Politique Scientifique Fédérale (Belgique) = Belgian Federal Science Policy ; Fonds de la Recherche Scientifique (Communauté française de Belgique) - F.R.S.-FNRS ; Région wallonne : Direction générale des Technologies, de la Recherche et de l'Energie - DGTRE
Researchers ; Professionals ; Students
http://hdl.handle.net/2268/3985

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