1-(4-fluorophenyl)ethanone semicarbazone

1-(4-fluorophenyl)ethanone semicarbazone,


This compound has been reported for the first time in 1995 by Dimmock et al. in a paper in the European Journal of Medicinal Chemistry:
JR Dimmock, KK Sidhu, SD Tumber, SK Basran, M Chen, JW Quail, J Yang, I Rozas and DF Weaver: Some aryl semicarbazones possessing anticonvulsant activities, Eur. J. Med. Chem. 30, 1995, 287-301.
Abstract: A number of aryl semicarbazones displayed anticonvulsant activity in the maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) screens when administered intraperitoneally to mice. When given by the oral route to rats, protection was afforded in the MES but not scPTZ tests. Correlations were noted between the σ and σ* values of the aryl substituents, the interplanar angles made by the aryl rings with the adjacent carbimino groups and the shapes of certain semicarbazones determined by X-ray crystallography, and the activities in the rat oral MES screen. Molecular modeling studies revealed a number of statistically significant descriptors which contributed to anticonvulsant activity.

    1H-NMR spectrum (300 MHz) of 1-4-Fluorophenyl-ethanon semicarbazon in DMSO-d6 Solvent signals at 2.5 ppm (DMSO-d5), about 3.3 ppm (water) and 0.0 ppm (not visible, internal standard TMS)

 13C-NMR spectrum, proton decoupled (75 MHz) of 1-4-Fluorophenyl-ethanon semicarbazon
in DMSO-d6, internal standard TMS

19F-NMR spectrum, proton coupled (282 MHz) of 1-(4-Fluorophenyl)ethanone semicarbazone
in DMSO-d6, internal standard CFCl3

1H,15N-NMR- HSQC spectrum of 1-(4-Fluorophenyl)ethanone semicarbazone in DMSO-d6

1H,15N-NMR- HMBC spectrum of 1-(4-Fluorophenyl)ethanone semicarbazone in DMSO-d6,
internal standard nitromethane

Complete assignment and coupling constants

 the protons of the aromatic ring form a n AA´XX´-multiplet, further split by the 3J and 4J fluorine proton couplings