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Crystal structure of cyclic dehydroaminoacid derivatives
I. Tetrasubstituted (Z)-5(4H)-oxazolones
Veröffentlicht/Copyright:
25. August 2010
Abstract
The crystal and molecular structures of two 5(4H)-oxazolones related to α,β-unsaturated amino acids have been determined from three-dimensional X-ray data.
C12H11NO2(1a) is orthorhombic, space group Pbca, Z = 8, a = 7.629(2) Å, b = 14.944(3) Å, c = 17.802(3) Å.
C17H13NO2(1b) is monoclinic, space group P21/n, Z = 8, a = 19.176(3) Å, b = 7.578(2) Å, c = 18.703(3) Å, β = 94.98(5)°.
The investigation of this series of “Z” 5(4H)-oxazolones having tetra-substituted exocyclic double bond provides, by comparison with studies of analogous systems, information on the conformational flexibility of α,β-unsaturated amino acid derivatives. The main peculiarity is the presence of an accepting nitrogen atom instead of an NH group. This allows fully planar conformations, at least to compounds having trisubstituted (“Z” or “E”) exocyclic double bond systems. The 1H-NMR spectra are also discussed.
Published Online: 2010-08-25
Published in Print: 1989
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