Synthesis of N-p-Fluorothiosemicarbazone and of Bis(N-p-Fluorophenylthiourea): Crystal Structure and Conformational Analysis of N,N′-Bis(4-Fluorophenyl)Hydrazine-1,2-Bis(Carbothioamide)
Résumé
The reaction of the phosphonated hydrazone (2-hydrazineylidenepropyl) diphenylphosphine oxide 1 with p-fluorophenyl-isothiocyanate yields as a major product the thiosemicarbazone Ph2P(=O)CH2{C=N-NH(C=S)-N(H)C6H4F}CH3 (2-(1-(diphenylphosphoryl)propan-2-ylidene)-N-(4-fluorophenyl)hydrazine-1-carbothioamide) 2 along with bis(N-p-fluorophenylthiourea) 3 as a minor product. The latter compound 3 was isolated as the main product by direct treatment of p-FC6H4N=C=S with hydrazine in a 2:1 ratio. Both 2 and 3 were characterized by NMR. Furthermore, the molecular structure of 3 was elucidated by an X-ray diffraction study, revealing both intra- and intermolecular secondary interactions. A conformational DFT study, at the B3LYP/6-311 G++ (d, p) level of theory, confirms a good match between the calculated structure and the experimental one.
Domaines
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