Abstract
Erythro- and threo-isomers of 2-(1-adamantyl)-3-hydroxybutyric acid ( 1) have been synthesized, separated and characterized by 1H NMR spectroscopy. The NMR study showed that threo- 1 is present predominantly in intramolecular H-bonded form, whereas there is a rotational mobility in erythro- 1. The conformations of erythro- and threo-isomers were examined computationally using the AMBER force field and density functional calculations. The computed results were found to be in agreement with the observed experimental results, that is threo- 1 was found to be intramolecularly hydrogen bonded, while the most stable conformation for erythro- 1 was non-hydrogen bonded. The large difference between the values of the vicinal coupling constant in 1H NMR obtained in CDCl 3, CD 3CN and d 6-DMSO can be an indicator for the intramolecular H-bonding in the cases when X-ray structural analysis and high-level computations are not possible.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
