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Intramoleculer Hydrogen Bonding In Epoxide, Thiirane, Aziridine And Phosphirane Containing Cyclopentanols, Ben Edward Smith
Intramoleculer Hydrogen Bonding In Epoxide, Thiirane, Aziridine And Phosphirane Containing Cyclopentanols, Ben Edward Smith
Electronic Theses and Dissertations
A recent computational analysis of the stabilizing intramolecular OH· · · O contact in 1,2-dialkyl-2,3-epoxycyclopentanol diastereomers has been extended to thiiriane, aziridine and phosphirane analogues. Density functional theory (DFT), second-order Møller-Plesset perturbation theory (MP2) and CCSD(T) coupled-cluster computations with simple methyl and ethyl substituents indicate that electronic energies of the cis isomers are lowered by roughly 3 to 4 kcal mol−1 when the OH group of these cyclopentanol systems forms an intramolecular contact with the O, S, N or P atom on the adjacent carbon. The results also suggest that S and P can participate in these stabilizing intramolecular interactions …