期刊
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY
卷 75, 期 -, 页码 623-+出版社
INT UNION CRYSTALLOGRAPHY
DOI: 10.1107/S2053229619005631
关键词
essential oil; sesquiterpene hydrocarbon; hemisynthesis; thiosemicarbazone; thiazolidinone; crystal structure; computational chemistry; C-H center dot center dot center dot Cl hydrogen bonding; corrosion; polarization; DFT; cyclic voltammetry
资金
- Region NPDC
- FEDER
- CNRS
- MESR
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)-[(1aR,5aR,9aS)-1,1-dichloro-1a, 5,5,7-tetramethyl-1a, 2,3,4,5,5a, 8,9-octahydro-1H-benzo[a] cyclopropa[b][7]annulen-8-ylidene]hydrazono}-4-oxothiazolidin-3-yl) acetate, C23H31Cl2N3O3S, 5, crystallizes in the orthorhombic noncentrosymmetric space group P2(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 center dot center dot center dot 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 H2SO4 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.
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