Conformational Analysis of 2-(1-Adamantyl)-3-Hydroxybutyric Acid by 1H NMR Spectroscopy and Computational Studies (CROSBI ID 134951)
Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija
Podaci o odgovornosti
Ganguli, Bishwajit ; Singh, Ajeet ; Basarić, Nikola ; Matković, Marija ; Mlinarić-Majerski, Kata
engleski
Conformational Analysis of 2-(1-Adamantyl)-3-Hydroxybutyric Acid by 1H NMR Spectroscopy and Computational Studies
Erythro- and threo- isomers of 2-(1-adamantyl)-3-hydroxybutiric acid (1) have been syntesized, separated and caracterized 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 filed 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 the values of the vicinal coupling constant in 1H NMR obtained in CDCl3, CD3CN and d6-DMSO can be an idicator for the intramolecular H-bonding in the case when X-ray structural analysis and high level computations are not possible.
Adamantane; Hidrogen bonds; DFT; NMR spectroscopy
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Podaci o izdanju
888 (1-3)
2008.
238-243
objavljeno
0022-2860
10.1016/j.molstruc.2007.12.022