Premium
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
Author(s) -
Bimoussa Abdoullah,
Koumya Yassine,
Abouelfida Abdesselam,
Ait Itto Moulay Youssef,
Benyaich Abdelaziz,
Mentre Olivier,
Ketatni El Mostafa,
Auhmani Aziz,
Auhmani Abdelwahed
Publication year - 2019
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229619005631
Subject(s) - orthorhombic crystal system , molecule , crystallography , crystal structure , chemistry , ring (chemistry) , crystal (programming language) , cyclohexene , single crystal , hydrogen bond , semicarbazone , stereochemistry , organic chemistry , computer science , programming language , catalysis
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.