Synthesis and crystal structure of new organic ligand based on s-methylisolthiosemicarbazide

Rotaru Mihaela; Cocu Maria; Dragancea Diana; Bulhak Ion; Bourosh Pavlina

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ROTARU, Mihaela, COCU, Maria, DRAGANCEA, Diana, BULHAK, Ion, BOUROSH, Pavlina. Synthesis and crystal structure of new organic ligand based on s-methylisolthiosemicarbazide. In: Ecological and environmental chemistry : - 2017, Ed. 6, 2-3 martie 2017, Chișinău. Chisinau, Republic of Moldova: Academy of Sciences of Moldova, 2017, Ediția 6, p. 188.

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Ecological and environmental chemistry
Ediția 6, 2017

Conferința "Ecological and environmental chemistry 2017"
6, Chișinău, Moldova, 2-3 martie 2017

Synthesis and crystal structure of new organic ligand based on s-methylisolthiosemicarbazide

Pag. 188-188

Rotaru Mihaela¹, Cocu Maria¹, Dragancea Diana¹, Bulhak Ion¹, Bourosh Pavlina²

¹ Institute of Chemistry of the Academy of Sciences of Moldova,
² Institute of Applied Physics, Academy of Sciences of Moldova

Disponibil în IBN: 18 martie 2019

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The new organic ligand, S-methylisolthiosemicarbazide of o-vanillin has been obtained by interaction of o-vanillin and S-methylisothiosemicarbazide (in molar ratio 1:1) in methanol. The compound is soluble in chloroform, dimethylformamide, less soluble in ethanol and methanol and insoluble in water. It has been characterized by IR spectroscopy and X-ray diffraction method. In the IR spectrum of potential coordinating agent is observed an intensification of the band at 1648 cm-1 assigned to ν(C=N), which is caused by condensation of o-vanillin and methylated thiosemicarbazide with formation of Schiff base. The characteristic bands of carbonyl and amino components also occur in condensation product. Thus, the bands at 3398 and 3311cm-1 are assigned to as and s (NH2), respectively and 1602cm-1 band to δ (NH2). A medium intensity broad band at 3113cm-1 is assigned to (OH) oscillations of associated group. Methyl groups are characterized by absorption bands in the 30002800cm-1 region  (CH3) and 1460 and 1380cm-1  δs and δas (CH3) respectively. As proof of the presence of carbonyl component (o-vanillin) are the most intense bands in the spectrum at 1239cm-1 assigned to (= CO-CH3) and the medium intensity band at 776cm-1 attributed to the presence of three neighboring hydrogen atoms in benzene ring and which demonstrate the type of substitution (1,2,3-) in it. Compound crystallizes in the monoclinic space group P21/n. The conformation of a planar molecule is stabilized by bifurcate intramolecular hydrogen bond O1–H···N1/S1, and thiosemicarbazide fragment adopts cis configuration (isomer Z) (Fig.). Bond distances in thiosemicarbazide fragment (N2–C8 1.303(3) Å, N3–C8 1.339(3) Å) indicate the localization of double and single bonds. Two NHN intermolecular H-bonds form R2 2 (8) synton and join the molecules into centrosymmetrical dimmer. Such dimmers are linked in the crystal by NHO intermolecular Hbonds.

The new organic ligand, S-methylisolthiosemicarbazide of o-vanillin has been obtained by interaction of o-vanillin and S-methylisothiosemicarbazide (in molar ratio 1:1) in methanol. The compound is soluble in chloroform, dimethylformamide, less soluble in ethanol and methanol and insoluble in water. It has been characterized by IR spectroscopy and X-ray diffraction method. In the IR spectrum of potential coordinating agent is observed an intensification of the band at 1648 cm-1 assigned to ν(C=N), which is caused by condensation of o-vanillin and methylated thiosemicarbazide with formation of Schiff base. The characteristic bands of carbonyl and amino components also occur in condensation product. Thus, the bands at 3398 and 3311cm-1 are assigned to as and s (NH2), respectively and 1602cm-1 band to δ (NH2). A medium intensity broad band at 3113cm-1 is assigned to (OH) oscillations of associated group. Methyl groups are characterized by absorption bands in the 30002800cm-1 region  (CH3) and 1460 and 1380cm-1  δs and δas (CH3) respectively. As proof of the presence of carbonyl component (o-vanillin) are the most intense bands in the spectrum at 1239cm-1 assigned to (= CO-CH3) and the medium intensity band at 776cm-1 attributed to the presence of three neighboring hydrogen atoms in benzene ring and which demonstrate the type of substitution (1,2,3-) in it. Compound crystallizes in the monoclinic space group P21/n. The conformation of a planar molecule is stabilized by bifurcate intramolecular hydrogen bond O1–H···N1/S1, and thiosemicarbazide fragment adopts cis configuration (isomer Z) (Fig.). Bond distances in thiosemicarbazide fragment (N2–C8 1.303(3) Å, N3–C8 1.339(3) Å) indicate the localization of double and single bonds. Two NHN intermolecular H-bonds form R2 2 (8) synton and join the molecules into centrosymmetrical dimmer. Such dimmers are linked in the crystal by NHO intermolecular Hbonds.

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