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Bis(3‐ endo ‐camphoryl)phosphinic Acid, a Non‐Racemic Helical Supramolecular Host with Aquapores
Author(s) -
Beckmann Jens,
Duthie Andrew,
Rüttinger Roman,
Schwich Torsten
Publication year - 2008
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.200800192
Subject(s) - supramolecular chemistry , chemistry , molecule , hydrogen bond , helix (gastropod) , crystallography , stereochemistry , crystal structure , organic chemistry , ecology , snail , biology
Bis(3‐ endo ‐camphoryl)phosphinic acid ( 1 ) was prepared by the reaction of the lithium enolate of D‐(+)‐camphor and phosphorous trichloride followed by an oxidative work up. Compound 1 crystallizes from wet toluene as monohydrate 1 ·H 2 O, which was investigated by X‐ray crystallography. Molecules of 1 are associated by strong hydrogen bonds giving rise to the formation of a supramolecular helix. The interior channel of the helix is filled by a one‐dimensional (1D) string of water molecules that are also associated by hydrogen bonding. The 1D string adopts a twisted zigzag conformation. Although the hydrogen bond networks are not cross‐linked both the screw of the helix and the twist of the 1D string of water molecules are left‐handed (M) and controlled by the chiral camphoryl residues situated on the exterior of the helix. The overall supramolecular structure is strongly reminiscent of aquaporin‐1, a significant membrane‐channel protein responsible for the transport of water into the cells.