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Synthesis of a Tight Intramolecular OH···Olefin Interaction, Probed by IR, 1H NMR, and Quantum Chemistry

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posted on 17.12.2015, 08:03 by Mark D. Struble, Maxwell Gargiulo Holl, Gavin Coombs, Maxime A. Siegler, Thomas Lectka
We have synthesized a molecule containing a tight hydrogen-bonding interaction between an alcohol and a nonconjugated π-system. The strength of this hydrogen bond results in a large red shift, nearly 189 cm–1, on the alcohol stretching frequency in the IR spectrum in comparison to a free alcohol control. The interaction is notable in that it possesses a better defined intramolecular hydrogen bond compared to the usual molecules for which it is noted, such as syn-7-norbornenol. This interaction was studied through the use of IR and NMR spectroscopy, X-ray crystallography, and molecular modeling calculations.