PREPARATION AND CHARACTERIZATION OF Cl3CC(S)NH2 BY TRADITIONAL AND NON-TRADITIONAL METHODS.

RODRIGO E. DOMINGUEZ; GUSTAVO G. ARGÜELLO; ANA G. IRIARTE

Carlos Paz, Córdoba

Conferencia; 13th Latin American Conference on Physical Organic Chemistry; 2015

ORGANIZING COMMITTEE, INFIQC, Universidad Nacional de Córdoba, Argentina.

PREPARATION AND CHARACTERIZATION OF Cl3CC(S)NH2 BY TRADITIONAL AND NON-TRADITIONAL METHODS. Rodrigo E. Domínguez, Gustavo A. Argüello, Ana G. Iriarte* INFIQC - Departamento de Fisicoquímica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba. Ciudad Universitaria, 5000 - Córdoba - Argentina. rdominguez@fcq.unc.edu.ar Thioamides are compounds widely used in organic chemistry, specially in the synthesis of heterocycles1 and thiopeptide antibiotics2. Particularly, the thioacetamide family have been studied thoroughly, not only experimentally but theoretically, because of their well-known ability to cause hepatotoxicity and/or carcinogenicity4 and due to their importance as peptidic bond model of some biological systems3. It is also widely known that the halogenated acetamide species are very important chemical precursors of compounds with biocide activity5,6. In this context, the posibility to obtain a compound with such interesting characteristics, i.e. with the C=S group and with halogen atoms in the same molecule, it is an intriguing task. Thus, in this work we present the synthesis of a novel compound, Cl3CC(S)NH2 (Triclhorothioacetamide, TCSA), obtained from the corresponding oxigenated acetamide. These preparations were performed using either a conventional method (heating at reflux) or by microwave and ultrasound techniques. In order to obtain the best condicions of reaction, sulfur solid was also used as reagent for the reactions. In all cases TCSA was obtained with yields that depend on the procedure used. The product was characterized by conventional techniques (H-RMN, C-RMN, HMBC, HMQC, IR, MS, UV-Vis), and the molecular structure and vibrational spectra was calculated by using Gaussian 09 program. Better yields were obtained by using microwaves and with CCl4 as solvent. The reaction also occurs succesfully using THF as solvent, but needing more time in comparison with the microwave technique. The theoretical calculations indicate that the compound belongs to the C1 group of symmetry, and the 21 normal modes of vibration were assigned. 1. T. S. Jagodziński, Chem. Rev., 2003, 103, 197?227. 2. M. C. Bagley, J. W. Dale, E. a. Merritt and X. Xiong, Chem. Rev., 2005, 105, 685?714. 3. Y. Hase, Spectrochim. Acta. A. Mol. Biomol. Spectrosc., 2000, 56, 1035?44. 4. E. Carolina, 1977. 5. A. G. Iriarte, E. H. Cutin and C. O. Della Védova, J. Mol. Struct., 2006, 800, 154?157. 6. A. G. Iriarte, E. H. Cutin and G. A. Argüello, Aust. J. Chem., 2011, 64, 1366?1372.