In 3-oxetanol, 3-cyclopenten-1-ol, and 2-indanol the position of the infrared OH stretching bands not only provides information about intramolecular hydrogen bonding but also about the structure of the ring and about the potential energy function for the ring puckering vibration.  Because the OH stretching band position is sensitive to its electronic environment the FTIR spectrum in cyclohexane solution can be used to determine both the OH rotamer type and the presence or absence of hydrogen bonding in such molecules.   Our group has recently measured the OH stretching bands of very dilute solutions of 3-oxetanol in cyclohexane to complement earlier similar studies we did for 3-cyclopenten-1-ol and 2-indanol.  The presence of a stable puckered ring with intramolecular hydrogen bonding is detected in all three molecules.  In 2-indanol the spectrum shows clear evidence of a double minimum for the ring-puckering vibration.  However, the results about the nature of the ring-puckering potential energy function are more ambiguous for the other two molecules.

Using infrared OH stretching bands to study intramolecular hydrogen bonding and ring puckering in cyclic alcohols

243rd National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.