In:
Acta Crystallographica Section C Structural Chemistry, International Union of Crystallography (IUCr), Vol. 75, No. 6 ( 2019-06-01), p. 623-632
Abstract:
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.
Type of Medium:
Online Resource
ISSN:
2053-2296
DOI:
10.1107/S2053229619005631
DOI:
10.1107/S2053229619005631/yo3060sup1.cif
DOI:
10.1107/S2053229619005631/yo3060Isup2.hkl
DOI:
10.1107/S2053229619005631/yo3060sup3.tif
DOI:
10.1107/S2053229619005631/yo3060sup4.tif
DOI:
10.1107/S2053229619005631/yo3060sup5.tif
DOI:
10.1107/S2053229619005631/yo3060sup6.tif
DOI:
10.1107/S2053229619005631/yo3060sup7.tif
DOI:
10.1107/S2053229619005631/yo3060sup8.tif
DOI:
10.1107/S2053229619005631/yo3060sup9.tif
DOI:
10.1107/S2053229619005631/yo3060sup10.tif
DOI:
10.1107/S2053229619005631/yo3060sup11.tif
DOI:
10.1107/S2053229619005631/yo3060sup12.tif
Language:
Unknown
Publisher:
International Union of Crystallography (IUCr)
Publication Date:
2019
detail.hit.zdb_id:
2025703-X
Permalink