Ethyl (2E)-2-(hydroxy-imino)propanoate.

ABSTRACT: The mol-ecule of the title compound, C(5)H(9)NO(3), is essentially planar [the maximum deviation for a non-H atom from the mean plane is 0.021 (3) Å] due to the π-conjugation of the hydroxy-imino and carbonyl groups, which are trans to each other; ab initio calculations in vacuo at the DFT (B3LYP/6-311G**++) level of theory confirmed that E conformer is indeed the lowest in energy. The packing in crystal structure is influenced by strong inter-molecular O-H⋯N hydrogen-bonding inter-actions between oxime groups and also by π-stacking of the mol-ecules due to the carbonyl and oxime group orbital overlap [inter-planar distance between adjacent mol-ecules = 3.143 (4) Å]. Jointly, these factors afford infinite 6.32 Å thick mol-ecular sheets, where the plane of each mol-ecule is perpendicular to

SUBMITTER: Nikolayenko IV 

PROVIDER: S-EPMC2983986 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature