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

Mark D. Struble | Zendy; Maxwell Gargiulo Holl | Zendy; Gavin Coombs | Zendy; Maxime A. Siegler | Zendy; Thomas Lectka | Zendy

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

Author(s) -

Mark D. Struble,

Maxwell Gargiulo Holl,

Gavin Coombs,

Maxime A. Siegler,

Thomas Lectka

Publication year - 2015

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.5b00470

Subject(s) - intramolecular force , hydrogen bond , chemistry , molecule , quantum chemistry , alcohol , infrared spectroscopy , spectroscopy , nuclear magnetic resonance spectroscopy , computational chemistry , crystallography , olefin fiber , photochemistry , stereochemistry , organic chemistry , supramolecular chemistry , catalysis , physics , quantum mechanics

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.

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