Internal rotation of intramolecular hydrogen bonding of OH or NH2 groups attached to three-membered ring molecules
Ocola, Esther Juliana
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https://hdl.handle.net/2142/104554
Description
Title
Internal rotation of intramolecular hydrogen bonding of OH or NH2 groups attached to three-membered ring molecules
Author(s)
Ocola, Esther Juliana
Contributor(s)
Laane, Jaan
Issue Date
2019-06-19
Keyword(s)
Non-covalent interactions
Abstract
The internal rotations about the single bonds connecting OH or \chem{NH_2} groups to cyclopropyl or cyclopropene rings were investigated. The experimental fits to the infrared data of the one-dimensional torsional potential energy functions were compared to theoretical calculations. MP2/cc-pVTZ and CCSD/cc-pVTZ computations were found to be in good agreement with the experimental results for cyclopropanol and cyclopropylamine. Calculations were also carried out on the internal rotations of 1-cyclopropen-1-ol and 2-cyclopropen-1-amine. Each of these molecules has a calculated energy minimum corresponding to a conformation with an intramolecular $\pi$-type hydrogen bond. The $\pi$-bonding stabilization is 2.3 kcal/mol for the alcohol and 2.5 kcal/mol for the amine. The calculated O-H, N-H, and C=C stretching frequencies are lower for the hydrogen bonded conformers than for the conformations without the $\pi$-type hydrogen bonds. The C=C bond stretching frequencies show the largest decreases resulting from the hydrogen bonding.
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