Synthesis and structure of dithiocarbonimidates derived from aromatic heterocycles: Role of weak interactions in the preferred conformation

• Published in: Journal of molecular structure Vol. 984; no. 1; pp. 409 - 415
• Main Authors: Peña-Hueso, Adrián, Téllez, Fabiola, Vieto-Peña, Rebeca, Esquivel, Rodolfo O., Esparza-Ruiz, Adriana, Ramos-García, Iris, Contreras, Rosalinda, Barba-Behrens, Norah, Flores-Parra, Angelina
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15.12.2010
• Subjects: Bonding; C [sbnd]H hydrogen bonds; Crystals; Diffraction; Dithiocarbonimidates; Iodides; Mass spectroscopy; Mathematical analysis; Molecular structure; Sulfur weak interactions; Synthesis; Sulfur weak interactions; Dithiocarbonimidates; C H hydrogen bonds
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2010.10.016

The synthesis and the structure of four dimethyldithiocarbonimidates: 1-methyl-2-dimethyldithiocarbonimidate-benzimidazole ( 1), 5-chloro-2-[dimethyldithiocarbonimidate]-benzoxazole ( 2), 1-methyl-2-[dimethyldithiocarbonimidate]-pyrimidinium iodide ( 3) and 1,4-dimethyl-6-oxo-2-[dimethyldithiocarbonimidate]-pyrimidine ( 4), were investigated by TOF mass spectra, NMR and X-ray diffraction analyses. It was found that the molecules were planar with preferred conformations dictated by intramolecular N → S interactions. In the crystals, dimers or polymers were stabilized through S⋯S, S⋯π and C H⋯Y (Y = S, O, N and π electrons) interactions. Calculations confirmed the weak interactions.