5-Mercapto-1,3,4-thiadiazole-2(3H)-thione: Synthesis and Structure of Alkylated Derivatives

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 char...

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Veröffentlicht in:Journal of heterocyclic chemistry 2014-05, Vol.51 (3), p.747-754
Hauptverfasser: Mistry, Jigar K., Dawes, Richard, Choudhury, Amitava, Van De Mark, Michael R.
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.1903