title: Synthesis of a Tight Intramolecular OH···Olefin Interaction, Probed by IR, (1)H NMR, and Quantum Chemistry.
abstract: 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.
authors.affiliation: Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218 United States.
authors.forename: Mark D
authors.initials: MD
authors.lastname: Struble
authors.affiliation: Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218 United States.
authors.forename: Maxwell Gargiulo
authors.initials: MG
authors.lastname: Holl
authors.affiliation: Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218 United States.
authors.forename: Gavin
authors.initials: G
authors.lastname: Coombs
authors.affiliation: Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218 United States.
authors.forename: Maxime A
authors.initials: MA
authors.lastname: Siegler
authors.affiliation: Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218 United States.
authors.forename: Thomas
authors.initials: T
authors.lastname: Lectka
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006878:Hydroxides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D011522:Protons; D011789:Quantum Theory; D013055:Spectrophotometry, Infrared
chemical_list: D000475:Alkenes; D006878:Hydroxides; D011522:Protons; C031356:hydroxide ion