Intramolecular Hydrogen Bonding in Α-Epoxy Alcohols: A Conformational Analysis of 1,2-Dialkyl-2,3-Epoxycyclopentanol Diastereomers
Abstract
Geometry optimizations for 11 1,2-disubstituted-2,3-epoxycyclopentanol diastereomers were studied using the M06-2X/cc-pVTZ method and basis set to probe mechanistic details in the α-epoxy alcohol semipinacol rearrangement reaction. Electronic energies of active cis diastereomers are on average 0.9 kcal mol11 lower than trans diastereomers. Intramolecular hydrogen bonding stabilizes the cis substrate energy by 3.4 kcal mol-1, on average.
Recommended Citation
Y. A. Abdo et al., "Intramolecular Hydrogen Bonding in Α-Epoxy Alcohols: A Conformational Analysis of 1,2-Dialkyl-2,3-Epoxycyclopentanol Diastereomers," Chemistry Letters, vol. 47, no. 2, pp. 156 - 159, Chemical Society of Japan; Oxford University Press, Jan 2018.
The definitive version is available at https://doi.org/10.1246/cl.170932
Department(s)
Chemistry
Keywords and Phrases
Density functional theory (DFT); Intramolecular hydrogen bonding; α-Epoxy alcohol
International Standard Serial Number (ISSN)
1348-0715; 0366-7022
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 2024 Chemical Society of Japan; Oxford University Press, All rights reserved.
Publication Date
01 Jan 2018
Comments
National Science Foundation, Grant 1430280