Structure of 4-(4-methoxyphenyl)thiosemicarbazide

Chattopadhyay, D.; Banerjee, T.; Majumdar, Swapan Kumar; Ghosh, Sourav Ranjan; Kuroda, Reiko

doi:10.1107/s0108270187093375

Cited by 21 publications

(17 citation statements)

References 11 publications

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“…It appears that substitution at the hydrazinic terminal nitrogen reduces its metal-chelating ability. The structures of thiosemicarbazide and its derivatives formed through amino-terminal nitrogen (Chattopadhyay, Banerjee, Mazumdar, Ghosh & Kuroda, 1987) and its metal complexes (Cavalca, Nardelli & Fava, 1962;Cavalca, Nardelli & Branchi, 1960) are available in the literature. Since the metal-chelating property is an important feature of thiosemicarbazide, it is of interest to determine the structure of derivatives of thiosemicarbazide with substitution at the hydrazinic terminal nitrogen.…”

Section: C12h9c1n2osmentioning

confidence: 99%

Structure of a carcinogenic agent: 1-formyl-3-thiosemicarbazide

Saxena¹,

Sinha²,

Singh³

1991

Acta Crystallogr C

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2374 C12H9C1N2OSuent to the desired position in the benzene ring. The results of the calculations are depicted in Figs. 2(a) and 2(b) for compounds (1) and (2), respectively.Independent of the alkylation position, the general profiles of the E=f(¢) curves are similar in both diagrams. Therefore, the conformers corresponding to a planar arrangement of the benzene and thiohydantoin rings (~ about 0 and 180 °) are in energy maxima. The two absolute minima-energy conformations are those in which the benzene ring is inclined to the thiohydantoin ring at almost 90 ° for all analyzed compounds. As is clearly visible, the effect of para and meta substitution is similar and both energy minima have similar heights. The heights of maxima in ortho-substituted compounds are different; those at ~ about 180 ° being much greater. The corresponding planar arrangement of both molecules with an ortho substituent is especially unfavourable.The differences in the conformational analysis results also depend on the dialkylation position (1,2-or 2,3-). The energy differences in 1,2-dialkylation products ( Fig. 2a) are much bigger and also the positions of the extremes are slightly shifted in comparison with 2,3-analogues (Fig. 2b).Summarizing, the energy differences between the conformers and the profiles of the curves suggest that the non-planar conformations for free molecules are preferred for all 1,2-dialkylated compounds. The para and meta substitutions in 2,3-dialkylated compounds generate no restrictions in the preferences of the conformations while for ortho substitution a planar molecule (~o = 180 °) is not favoured. The planar conformation for (2p) in the solid state should therefore be a consequence of molecular packing in the crystal.

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Section: C12h9c1n2osmentioning

confidence: 99%

Structure of a carcinogenic agent: 1-formyl-3-thiosemicarbazide

Saxena¹,

Sinha²,

Singh³

1991

Acta Crystallogr C

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“…The compound crystallizes into a monoclinic lattice with space group P2 1 /c. A torsion angle value of 178.1(1)°corresponding to the S(1)-C(1)-N(2)-N(3) moiety confirms the trans configuration to the thiocarbonyl S(1) atom with respect to the hydrazine nitrogen atom N(3) [14]. The N(2)-N(3) bond distance of 1.368(2) Å is closer to single bond distance (1.45 Å ) than to double bond distance (1.25 Å ) [15,20].…”

Section: Crystal Structuresmentioning

confidence: 67%

“…Thiosemicarbazones and their metal complexes have attracted considerable attention because of their wide-ranging biological activities, analytical applications and specific structures and chemical properties [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16]. Single crystals of thiosemicarbazone derivatives were grown and identified by spectroscopy and X-ray diffraction [15,16].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and crystal structure of cobalt(II) complex with 2-oximino-3-thiosemicarbazone-2,3-butanedione

Choi

Park

2007

Struct Chem

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The reaction of cobalt(II) chloride with the tridentate ligand 2-oximino-3-thiosemicarbazone-2,3-butanedione [Hotsb (1)] leads to the formation of the novel six-coordinated complex [Co(otsb) 2 ]Á2H 2 O (2). This complex has been synthesized and characterized by X-ray crystallography, spectroscopic and cyclic voltammetric measurements. The ligand Hotsb (1) obtained by the condensation of 2,3-butanedione monoxime and thiosemicarbazide is used for the preparation of complex 2. The Hotsb (1) crystallizes into a monoclinic lattice with space group P2 1 /c. The crystal structure of 2 shows a distorted mer-octahedral geometry in which the ligands are coordinated as uninegatively charged tridentate chelating agents via the hydrazine nitrogen atoms, the azomethine nitrogen atoms, and the thiolate sulfur atoms. The cyclic voltammogram of 2 undergoes two irreversible one-electron waves corresponding to Co II /Co III and Co II /Co I processes.

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“…The asymmetric unit contains two crystallographically independent molecules (A and B). The thiosemicarbazone moieties in both the molecules are planar and adopt an extended conformation, which can be seen from the conformation angles for the molecules A and B respectively [10,25,26].…”

Section: Structure Solutionmentioning

confidence: 96%

“…These include antileukemic [4][5][6], antituberculosis, antimalarial [7], antileprotic [8], antimicrobial [9][10][11] and antitumour activities [12,13]. Heterocyclic thiosemicarbazones possess antitumour properties and the ability to inhibit the enzyme ribonucleoside diphosphate reductase (RDR), an essential intermediate in DNA synthesis [14].…”

Section: Introductionmentioning

confidence: 99%