Web Release Date: December 21,
Short Strong Hydrogen Bonds in 2-Acetyl-1,8-dihydroxy-3,6-dimethylnaphthalene: An Outlier to Current Hydrogen Bonding Theory?
rensen,
and
tt*
Center for Insoluble Protein Structures and Interdisciplinary Nanoscience Center, Department of Chemistry, University of Aarhus, 8000 Aarhus C, Denmark
Received: July 10, 2006
In Final Form: November 6, 2006
Abstract:
The environmental influence on the electronic character of two O-H···O hydrogen bonds in a 
-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.
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