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1-(2-Cyclohex-2-enylpropionyl)-3-methylurea, 2-ethyl-5-methylhexanamide and 2-ethylpentanamide: three products of barbiturate decomposition

Lookup NU author(s): Gary Nichol, Emeritus Professor Bill CleggORCiD


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The three title compounds were obtained by reactions which mimic, with more extreme conditions, the in vivo metabolism of barbiturates. 1-(2-Cyclohex-2-enylpropionyl)-3-methylurea, C11H18N2O2, (I), and 2-ethylpentanamide, C8H17NO, (III), both crystallize with two unique molecules in the asymmetric unit; in the case of (III), one unique molecule exhibits whole-molecule disorder. 2-Ethyl-5-methylhexanamide, C9H19NO, (II), crystallizes as a fully ordered molecule with Z' = 1. In the crystal structures, three different hydrogen-bonding motifs are observed: in (I) a combination of R (2) 2(4) and R (2) 2(8) motifs, and in (II) and (III) a combination of R (4) 2(8) and R (2) 2(8) motifs. In all three structures, one-dimensional ribbons are formed by N-H...O hydrogen-bonding interactions.

Publication metadata

Author(s): Nichol GS, Clegg W

Publication type: Article

Publication status: Published

Journal: Acta Crystallographica, Section C: Crystal Structure Communications

Year: 2011

Volume: 67

Issue: 1

Pages: O13-O17

Print publication date: 01/01/2011

ISSN (print): 0108-2701

ISSN (electronic): 1600-5759

Publisher: Wiley-Blackwell Publishing, Inc.


DOI: 10.1107/S0108270110049322


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