Clathrate-type complexation of cephalosporins with beta-naphthol Version 4.0

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Clathrate-type complexation of cephalosporins with beta-naphthol
Kemperman GJ, de Gelder R, Dommerholt FJ, Raemakers-Franken PC, Klunder AJH, Zwanenburg B
CHEMISTRY-A EUROPEAN JOURNAL 5: (7) 2163-2168 JUL 1999

Document type: Article

Language: English

Cited References: 14

Times Cited: 0

Abstract:
The cephalosporin derivatives cephradine, cephalexin, cefaclor, and cefadroxil form complexes with beta-naphthol, provided water is present. The crystal structures of these complexes have been determined by single-crystal X-ray diffraction, The complexes appear to be inclusion compounds of the clathrate type. In all cases, the cephalosporin molecules play the role of host, while beta-naphthol is the guest molecule. Water molecules, which are accommodated in the crystal, play an essential role in the interaction between the guest and host molecules. Cephradine, cephalexin, and cefaclor form isomorphous complexes with beta-naphthol, whereas cefadroxil crystallizes in a different morphology. The crystal structures are described in detail and discussed in terms of hydrogen-bonding, van der Waals and electrostatic interactions. The structure of the cefadroxil complex is basically different from that of the other three complexes, although there are notable structural similarities.

Author Keywords:
cephalosporin, clathrates, hydrogen bonds, molecular recognition

KeyWords Plus:
CEFADROXIL

Addresses:
Zwanenburg B, Catholic Univ Nijmegen, Dept Organ Chem, NSR Ctr Mol Struct Design & Synth, NL-6525 ED Nijmegen, Netherlands.
Catholic Univ Nijmegen, Dept Organ Chem, NSR Ctr Mol Struct Design & Synth, NL-6525 ED Nijmegen, Netherlands.
Catholic Univ Nijmegen, Dept Inorgan Chem, NSR Ctr Mol Struct Design & Synth, NL-6525 ED Nijmegen, Netherlands.
DSM Res, Dept Organ Chem & Biotechnol, NL-6160 MD Geleen, Netherlands.

Publisher:
WILEY-V C H VERLAG GMBH, BERLIN

IDS Number:
217EW

ISSN:
0947-6539

Article 6 of 38