Intramolecular π-Type Hydrogen Bonding and Conformations of 3-Cyclopenten-1-ol. 1. Theoretical Calculations
- 24 June 2010
- journal article
- Published by American Chemical Society (ACS) in The Journal of Physical Chemistry A
- Vol. 114 (28), 7453-7456
- https://doi.org/10.1021/jp103404e
Abstract
The 3-cyclopenten-1-ol (3CPOL) molecule possesses two large-amplitude, low-frequency vibrations, namely, the ring-puckering and OH internal rotation, which can interconvert its four conformers into each other. Ab initio and density functional theory (DFT) calculations have been carried out to understand the energetics of these conformational changes. The lowest energy 3CPOL conformer possesses weak π-type intramolecular hydrogen bonding between the hydroxyl hydrogen and the carbon−carbon double bond, and this lies 274 cm−1 (0.78 kcal/mol) to 420 cm−1 (1.20 kcal/mol) lower in energy than the other three conformations according to CCSD/6-311++G(d,p) computations. The two-dimensional potential energy surface for 3CPOL was computed as a function of the ring-puckering and OH internal rotation coordinates with the MP2/6-31+G(d,p) model.Keywords
This publication has 25 references indexed in Scilit:
- Cooperativity in multiple unusual weak bondsTheoretical Chemistry Accounts, 2009
- The Nature of the Hydrogen BondPublished by Oxford University Press (OUP) ,2009
- Spectroscopic and Computational Studies of the Intramolecular Hydrogen Bonding of 2-IndanolThe Journal of Physical Chemistry A, 2006
- The π-type hydrogen bond with triple C–C bond acting as a proton-acceptor. A gradient-corrected hybrid HF-DFT and MP2 study of the phenol–acetylene dimer in the neutral S0 ground stateChemical Physics, 2006
- The conformational composition of 3-buten-1-ol, the importance of intramolecular hydrogen bondingJournal of Molecular Structure, 1998
- A study of the aluminum hydride reduction of unsaturated cyclic epoxidesTetrahedron Letters, 1994
- The effect of alkyl substitution on the conformation of intramolecularly hydrogen bonded β-γ (enolic) unsaturated alcoholsSpectrochimica Acta Part A: Molecular Spectroscopy, 1988
- Conformation of Allylic Alcohols and Intramolecular Hydrogen Bonding.Acta Chemica Scandinavica, 1986
- Intramolecular Interaction between Hydroxyl Group and π-Electrons. II. Limitation of the Interaction by Chain-length in ω-Hydroxy-1-alkenesBulletin of the Chemical Society of Japan, 1959
- INTRAMOLECULAR HYDROGEN BONDING INVOLVING DOUBLE BONDS, TRIPLE BONDS AND CYCLOPROPANE RINGS AS PROTON ACCEPTORSJournal of the American Chemical Society, 1958