Crystal structures of 2-formyl-6-methyl- and 6-bromo-2-formylpyridine 4-phenylthiosemicarbazones
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CTURE OF ORGANIC COMPOUNDS
Crystal Structures of 2Formyl6Methyl and 6Bromo2Formylpyridine 4Phenylthiosemicarbazones Yu. M. Chumakova, V. I. Tsapkovb, B. Ya. Antosyaka, Yu. A. Simonova†, S. Ianellic, N. N. Bairacb, A. P. Guleab, and S. A. PalomaresSanchezd a
Institute of Applied Physics, Academy of Sciences of Moldova, ul. Academiei 5, Chisinau, MD2028 Republic of Moldova email: [email protected] b Moldova State University, ul. Matteevicha 60, Chisinau, 277009 Republic of Moldova c Institute of Materials for Electronics and Magnetism, National Research Council, Parma, 43100 Italy d Autonomous University of San Luis Potosi. Alvararo Obregön 64, San Luis Potosi, 78000 Mexico Received February 19, 2010
Abstract—New thiosemicarbazones—2formyl6methylpyridine 4phenylthiosemicarbazone (I) and 6 bromo2formylpyridine 4phenylthiosemicarbazone hydrate (II)—were synthesized and their structures were determined. Molecules I and II are nonplanar, the phenyl moiety at the terminal nitrogen atom being rotated by 19.9° and 39.5°, respectively. The water molecule is the main factor determining the crystal pack ing of molecules II. DOI: 10.1134/S1063774510061033
INTRODUCTION
EXPERIMENTAL
Thiosemicarbazide and its derivatives R1R2N1– form stable coordination N compounds with virtually all transition metals. The properties of these compounds, which serve as the starting materials for the design of pharmaceutical products, depend on the nature of the substituents at the terminal nitrogen atoms. This class of compounds has found use in the treatment of many diseases [1]. The aims of preparative chemistry are, in particu lar, to synthesize new thiosemicarbazide derivatives and determine their physicochemical properties and structures. It was shown [2–6] that the biological activity of the compounds correlates well with their structures. Hence, the synthesis of thiosemicarbazide derivatives and investigation of their structural features are of both scientific and practical interest. In this study we report on the crystal structures of 2formyl6methylpyridine 4phenylthiosemicarba zone (I) and 6bromo2formylpyridine 4phenylthi osemicarbazone hydrate (II) determined by Xray dif fraction.
Synthesis
2H–C3(=S)–N4R3R4
R N
Compound I was synthesized according to the fol lowing procedure. A solution of 4phenylthiosemicar bazide (10 mmol) in ethanol (30 mL) was added with stirring and heating (50–55°С) in a water bath to a solution containing 2formyl6methylpyridine (10 mmol) in ethanol (20 mL). This led to the forma tion of a pale orange solution. The slow evaporation of the latter overnight afforded a yelloworange fine crystalline substance (in 60% yield), which was washed with a small amount of ethanol and dried in air. The composition was determined by elemental analysis. Found, %: С, 61.97; Н, 5.01; N, 20.48; S, 11.70. For C14H14N4S anal. calcd., %: С, 62.20; Н, 5.22; N, 20.72; S, 11.86.
Compound II was synthesized in a 69% yield of the theoretical value by the reaction of ethanolic solutions of 6
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