(E)-Methyl 2-[(2-fluorophenyl)aminomethylene]-3-oxobutanoate: X-ray and density functional theory (DFT) study
Journal article, 2009

The title compound, C12H12FNO3, a potential precursor for fluoroquinoline synthesis, is essentially planar, with the most outlying atoms displaced from the best-plane fit through all non-H atoms by 0.163(2) and 0.118(2) Å. Molecules are arranged in layers oriented parallel to the (011) plane. The arrangement of the molecules in the structure is controlled mainly by electrostatic interactions, as the dipole moment of the molecule is 5.2 D. In addition, the molecules are linked by a weak C-H...O hydrogen bond which gives rise to chains with the base vector [1,1,1]. Electron transfer within the molecule is analysed using natural bond orbital (NBO) analysis. Deviations from the ideal molecular geometry are explained by the concept of non-equivalent hybrid orbitals.

natural bond orbital analysis

X-ray strycture determination

DFT calculations

Author

Vratislav Langer

Chalmers, Chemical and Biological Engineering, Environmental Inorganic Chemistry

Pavel Mach

Slovak Academy of Sciences

Lubomír Smrcok

Slovak Academy of Sciences

Viktor Milata

Slovak University of Technology Bratislava

Acta Crystallographica Section C: Crystal Structure Communications

0108-2701 (ISSN) 1600-5759 (eISSN)

Vol. C65 4 o183-o185

Subject Categories

Inorganic Chemistry

Theoretical Chemistry

Organic Chemistry

DOI

10.1107/S0108270109009391

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Latest update

9/6/2018 1