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Issue 2, 2011
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Chemical reactions inside structured nano-environment: SN2 vs. E2 reactions for the F + CH3CH2Cl system

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Abstract

A new receptor for SN2 transition states, named NPTROL, is proposed. This molecule has a cavity and four hydroxyl groups that are able to interact with ionic SN2 and E2 transition states. Its catalytic effect and selectivity was investigated through high level ab initio calculations using the fluoride ion plus ethyl chloride in DMSO solution as a model system. Calculations at the ONIOM[CCSD(T)/6-311+G(2df,2p) : MP2/BASIS1] level of theory and solvent effects, included through a continuum solvation model, indicate that NPTROL is able to catalyze the SN2 pathway and has an inverse effect on the E2 pathway. Inside the NPTROL cavity, the ΔG for the SN2 transition state is 5.00 kcal mol−1 lower than that for E2, and as a consequence this reaction becomes highly selective toward the SN2 product.

Graphical abstract: Chemical reactions inside structured nano-environment: SN2 vs. E2 reactions for the F− + CH3CH2Cl system

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Publication details

The article was received on 14 Jul 2010, accepted on 27 Sep 2010 and first published on 29 Oct 2010


Article type: Paper
DOI: 10.1039/C0CP01182G
Citation: Phys. Chem. Chem. Phys., 2011,13, 779-782
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    Chemical reactions inside structured nano-environment: SN2 vs. E2 reactions for the F + CH3CH2Cl system

    J. R. Pliego Jr., Phys. Chem. Chem. Phys., 2011, 13, 779
    DOI: 10.1039/C0CP01182G

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