Hemisynthesis, crystal structure and inhibitory effect of sesquiterpenic thiosemicarbazones and thiazolidin-4-ones on the corrosion behaviour of stainless steel in 1 M H 2 SO 4 solution
Résumé
Treatment of thiosemicarbazones prepared from sesquiterpenes with ethyl 2-bromoacetate in the presence of sodium acetate afforded the corresponding thiazolidin-4-ones. The structures of all the newly synthesized compounds were established by considering spectral and single-crystal X-ray diffraction data. The title compound, ethyl 2-(( Z )-2-{( Z )-[(1a R ,5a R ,9a S )-1,1-dichloro-1a,5,5,7-tetramethyl-1a,2,3,4,5,5a,8,9-octahydro-1 H -benzo[ a ]cyclopropa[ b ][7]annulen-8-ylidene]hydrazono}-4-oxothiazolidin-3-yl)acetate, C 23 H 31 Cl 2 N 3 O 3 S, 5 , crystallizes in the orthorhombic noncentrosymmetric space group P 2 1 2 1 2 1 with Z = 4. Within the molecule in the crystal structure, the cyclohexene ring has an envelope conformation and the cycloheptane ring, to which it is fused, has a boat conformation. In the crystal, molecules are linked by C—H...Cl hydrogen bonds forming chains propagating along the b -axis direction. The absolute configuration of the molecule in the crystal could be fully confirmed from anomalous dispersion effects [Flack parameter = −0.04 (2)]. Thiosemicarbazones 1 and 2 are efficient inhibitors for steel corrosion in 1 M H 2 SO 4 solution, with a maximum efficiency of 92.28% at 10 −3 M . Furthermore, thiosemicarbazone compounds were found to be more efficient than thiazolidin-4-one derivatives. In addition, cyclic voltammetry was used to characterize the tested molecules, as well to estimate the experimental value of the energy band gap.
Origine : Fichiers produits par l'(les) auteur(s)