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

We have synthesized a molecule containing a tight hydrogen-bonding interaction between an alcohol and a nonconjugated pi-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...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 80; no. 9; pp. 4803 - 4807
Main Authors Struble, Mark D., Holl, Maxwell Gargiulo, Coombs, Gavin, Siegler, Maxime A., Lectka, Thomas
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 01.05.2015
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PI-INTERACTIONS
SHIFT
NMR
CAMBRIDGE STRUCTURAL DATABASE
SPECTROSCOPY
MOLECULE
COMPLEXES
SYSTEMS
HYDROGEN-BONDS
WATER
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Summary:We have synthesized a molecule containing a tight hydrogen-bonding interaction between an alcohol and a nonconjugated pi-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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b00470