X-ray diffraction evidence for aromatic π hydrogen bonding to water

The interaction of water with aromatic moieties is of importance in biological systems, as most encounter an aqueous environment during their normal functions. For example, common constituents of globular proteins such as phenylalanine, tryptophan and tyrosine possess aromatic side-chains1 that may...

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Bibliographic Details
Published in:Nature (London) 1991-02, Vol.349 (6311), p.683-684
Main Authors: Atwood, Jerry L, Hamada, Fumio, Robinson, Kerry D, Orr, G. William, Vincent, Rebecca L
Format: Article
Language:English
Subjects:
Aqueous environments
Aromatic compounds
Calixarenes
Chemical bonds
Condensed matter: structure, mechanical and thermal properties
Crystal structure
Exact sciences and technology
Fourier transforms
Holes
Hydrocarbons
Hydrogen
Hydrogen bonding
Hydrogen bonds
Hydrophobicity
Inorganic compounds
Low temperature
Metal complexes
Molecular structure
Phenylalanine
Physics
Proteins
Structure of solids and liquids
crystallography
Structure of specific crystalline solids
Tryptophan
Tyrosine
Water chemistry
X-ray diffraction
X-rays
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Summary:The interaction of water with aromatic moieties is of importance in biological systems, as most encounter an aqueous environment during their normal functions. For example, common constituents of globular proteins such as phenylalanine, tryptophan and tyrosine possess aromatic side-chains1 that may encounter water molecules inside the protein structure2. As a model for hydrogen-bonding interactions with aromatics, we have performed X-ray diffraction studies on crystalline Na4[calix[4]arene sulphonate]-13.5H20. Calixarene molecules3'4 contain hydrophobic cavities comprised of aromatic groups, rimmed, in the case of the water-soluble sulphonates (R = -S03Na), by hydrophilic groups5,6. In the absence of a hydrophobic guest, the cavity invariably contains a water molecule. The low-temperature X-ray crystal structure of this compound (see Table 1 and Fig. 1) shows direct evidence for hydrogen bonding between water and the aromatic it electrons in the solid state.
ISSN:0028-0836
1476-4687
DOI:10.1038/349683a0