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- W2019626269 abstract "Abstract Many qualitative, semi-quantitative and transition state models have been developed to rationalize and predict the π-face selectivity of various nucleophilic, electrophilic and radical organic reactions. However, there are cases where such models and theories are unable to explain the face selectivity. 5-Fluoro-2-methyleneadamantane ( I ) represents one such case to understand the stereoinduction with per-acid, where much discussed orbital and electrostatic models fail to explain the observed stereoselectivity. This work is focused with the rationalization and prediction of stereoselective electrophilic addition of per-acid to I using quantum chemical and molecular dynamics studies. The importance of solvent in controlling the π-face selectivity of I is reported employing ab initio and DFT studies. We have also presented here the effect of distortional asymmetry in the π-face of 5-Fluoro-2-methyleneadamantane ( I ) in solvent, which leads to predict the correct observed stereoselectivity. The ab initio molecular dynamics (AIMD) calculations attribute the asymmetric distortions in the ground state of I , which can be a constituent of the bulk transitional state differential for this reaction. The sterically unbiased olefins 4-substituted 9-methylenenorsnoutanes ( II ) and 5,6-cis,exo-disubstituted bicyclic[2.2.2]oct-2-enes ( III ) have also been studied as reference in the present study." @default.
- W2019626269 created "2016-06-24" @default.
- W2019626269 creator A5018868874 @default.
- W2019626269 creator A5023127670 @default.
- W2019626269 date "2013-12-01" @default.
- W2019626269 modified "2023-09-27" @default.
- W2019626269 title "Probing the role of solvation in predicting the π-facial selectivity of 5-Fluoro-2-methyleneadamantane with per-acid: A case study" @default.
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