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5-Mercapto-1,3,4-thiadiazole-2(3H)-thione: Synthesis and Structure of Alkylated Derivatives
Journal of Heterocyclic Chemistry
  • Jigar K. Mistry
  • Richard Dawes, Missouri University of Science and Technology
  • Amitiva Choudhury, Missouri University of Science and Technology
  • Michael R. Van-De-Mark, Missouri University of Science and Technology
The observed structure of 1,3,4-thiadiazolidine-2,5-dithione (also known as 2,5-dimercapto-1,3,4-thiadiazole) has been previously reported in three different tautomeric forms including - dithiol and - dithione. This report examines the relative stability of each form and also reports synthesis and characterization of the structures of mono-alkylated and di-alkylated forms of 5-mercapto-1,3,4-thiadiazole-2(3H)-thione. The methods of X-ray crystallography, NMR spectroscopy, and ab initio electronic structure calculations were combined to understand the reactivity and structure of each compound.
Research Center/Lab(s)
Center for High Performance Computing Research
Keywords and Phrases
  • 2,5 bis(methylthio)1,3,4 thidiazole 2 thiol,
  • 2,5 bis(thioaceticacid) 1,3,4 thiadiazole,
  • 5 (methylthio) 1,3,4 thidiazole 2(3h) thione,
  • 5 mercapto 1,3,4 thiadiazole 2(3h) thione,
  • dithiol derivative,
  • methyl chloride,
  • methyl iodide,
  • thiadiazole derivative,
  • unclassified drug,
  • ab initio calculation,
  • alkylation,
  • article,
  • drug stability,
  • drug structure,
  • drug synthesis,
  • methylation,
  • nuclear magnetic resonance spectroscopy,
  • solvation,
  • thermodynamics,
  • X ray crystallography
Document Type
Article - Journal
Document Version
File Type
© 2013 HeteroCorporation, All rights reserved.
Publication Date
Citation Information
Jigar K. Mistry, Richard Dawes, Amitiva Choudhury and Michael R. Van-De-Mark. "5-Mercapto-1,3,4-thiadiazole-2(3H)-thione: Synthesis and Structure of Alkylated Derivatives" Journal of Heterocyclic Chemistry Vol. 51 Iss. 3 (2014) p. 747 - 754 ISSN: 0022-152X
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