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Hydrogen bonding interaction of diphenylhydantoin and 9-ethyladenine

D Mastropaolo, A Camerman and N Camerman

A hydrogen-bonded complex of diphenylhydantoin (DPH) and 9-ethyladenine (EtAd) crystallizes from 2,4-pentanedione with the asymmetrical unit consisting of two DPH molecules, one EtAd molecule, and one solvent molecule. The crystal structure was solved by direct methods and refined to a residual of R = 0.054. Structure determination reveals that one DPH hydrogen-bonds to EtAd in a Watson-Crick scheme while the second DPH N(3)--H bonds to EtAd N(3) to form a 2:1 DPH-EtAd complex. Comparisons are made with barbiturate-adenine complexes and with an earlier postulation of a 1:1 DPH-EtAd complex derived from NMR and IR data. The 2,4-pentanedione molecule adopts the keto-enol configuration with an asymmetrical intramolecular hydrogen bond.

Volume 23, Issue 2, pp. 273-277, 03/01/1983
Copyright © 1983 by American Society for Pharmacology and Experimental Therapeutics






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Copyright © 1983 by the American Society for Pharmacology and Experimental Therapeutics