title: Short strong hydrogen bonds in 2-acetyl-1,8-dihydroxy-3,6-dimethylnaphthalene: an outlier to current hydrogen bonding theory?
abstract: The environmental influence on the electronic character of two O-H...O hydrogen bonds in a beta-diketone, 2-acetyl-1,8-dihydroxy-3,6-dimethylnaphthalene, is studied by low-temperature synchrotron X-ray diffraction and high-level density functional theory (DFT) calculations. It is revealed that one of the hydrogen bonds is very strong, yet partial localization is found. This result is analyzed by atoms in molecules (AIM) theory and applying the source function. Model compounds, with less steric strain, reveal that the strong hydrogen bond is not merely a result of steric compression.
authors.affiliation: Center for Insoluble Protein Structures and Interdisciplinary Nanoscience Center, Department of Chemistry, University of Aarhus, 8000 Aarhus C, Denmark.
authors.forename: Jesper
authors.initials: J
authors.lastname: Sørensen
authors.forename: Henrik F
authors.initials: HF
authors.lastname: Clausen
authors.forename: Rasmus D
authors.initials: RD
authors.lastname: Poulsen
authors.forename: Jacob
authors.initials: J
authors.lastname: Overgaard
authors.forename: Birgit
authors.initials: B
authors.lastname: Schiøtt
mesh_terms: D002627:Chemistry, Physical / Q000379:methods*; D004583:Electrons; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D013237:Stereoisomerism; D014961:X-Ray Diffraction
chemical_list: C520477:2-acetyl-1,8-dihydroxy-3,6-dimethylnaphthalene; D009281:Naphthalenes