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- Title
Special features of the nucleophilic substitution of halogen in alkyl and benzyl halides with anions generated from 4-hydroxy-2-mercapto-6-methylpyrimidine.
- Authors
Rakhimov, A.; Titova, E.; Fedunov, R.; Babkin, V.
- Abstract
The nucleophilic substitution of halogen (chlorine, bromine, and iodine) in alkyl and benzyl halides has been effected in aqueous dioxane media with S-and O-anions generated from 4-hydroxy-2-mercapto-6-methylpyrimidine. Under these conditions replacement of halogen proceeds by an SN2 mechanism and the reactivity of S-anions is 10 times greater than that of O-anions, which is in agreement with the results of ab initio quantum-chemical calculations of the electronic structure and total energy of transition states, carried out within the framework of the restricted Hartree-Fock method, basis 6-31G**.
- Subjects
HALOGENS; HALIDES; ANIONS; HARTREE-Fock approximation; ORGANIC oxides
- Publication
Chemistry of Heterocyclic Compounds, 2008, Vol 44, Issue 6, p700
- ISSN
0009-3122
- Publication type
Article
- DOI
10.1007/s10593-008-0105-6