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The LUMO energies of the α- and β-epoxides were determined by Spartan (v60, Wavefunction Inc; Irvine, CA; Hartree Fock/6-31G** basis set) as 0.10199 and 0.10452 hartree, respectively. A LUMO-HOMO energy gap between the Orbitals of the epoxide isomers and the HOMO orbital of the nucleophile (benzenethiol) was calculated and shown to favor the α-epoxide by 1.59 kcal/ M.
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The LUMO energies of the α- and β-epoxides were determined by Spartan (v60, Wavefunction Inc; Irvine, CA; Hartree Fock/6-31G** basis set) as 0.10199 and 0.10452 hartree, respectively. A LUMO-HOMO energy gap between the Orbitals of the epoxide isomers and the HOMO orbital of the nucleophile (benzenethiol) was calculated and shown to favor the α-epoxide by 1.59 kcal/ M.
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9
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33746916416
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The bulkier β-ketoester group occupies the less congested convex face, while the methyl group occupies the concave face. For a similar result, see
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53049100821
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The supplementary crystallographic data can be obtained free of charge from The Cambridge Crystallographic Data Centre, ref. no. CCDC 678950, via
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The supplementary crystallographic data can be obtained free of charge from The Cambridge Crystallographic Data Centre, ref. no. CCDC 678950, via www.ccdc.cam.ac.uk/data_request/cif.
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