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

Jigar K. Mistry; Richard Dawes; Amitiva Choudhury; Michael R. Van-De-Mark

doi:10.1002/jhet.1903

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

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	American English
Journal	Journal of Heterocyclic Chemistry
Volume	51
DOIs	https://doi.org/10.1002/jhet.1903
State	Published - May 1 2014

Keywords

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

Disciplines

Chemistry
Numerical Analysis and Scientific Computing

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https://doi.org/10.1002/jhet.1903

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

abstract = " 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.",

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author = "Mistry, \{Jigar K.\} and Richard Dawes and Amitiva Choudhury and Van-De-Mark, \{Michael R.\}",

year = "2014",

month = may,

day = "1",

doi = "10.1002/jhet.1903",

language = "American English",

volume = "51",

journal = "Journal of Heterocyclic Chemistry",

issn = "1943-5193",

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T1 - 5-Mercapto-1,3,4-thiadiazole-2(3H)-thione: Synthesis and Structure of Alkylated Derivatives

AU - Mistry, Jigar K.

AU - Dawes, Richard

AU - Choudhury, Amitiva

AU - Van-De-Mark, Michael R.

PY - 2014/5/1

Y1 - 2014/5/1

N2 - 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.

AB - 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.

KW - 2,5 bis(methylthio)1,3,4 thidiazole 2 thiol

KW - 2,5 bis(thioaceticacid) 1,3,4 thiadiazole

KW - 5 (methylthio) 1,3,4 thidiazole 2(3h) thione

KW - 5 mercapto 1,3,4 thiadiazole 2(3h) thione

KW - dithiol derivative

KW - methyl chloride

KW - methyl iodide

KW - thiadiazole derivative

KW - unclassified drug

KW - ab initio calculation

KW - alkylation

KW - article

KW - drug stability

KW - drug structure

KW - drug synthesis

KW - methylation

KW - nuclear magnetic resonance spectroscopy

KW - solvation

KW - thermodynamics

KW - X ray crystallography

UR - https://scholarsmine.mst.edu/chem_facwork/2197

UR - https://doi.org/10.1002/jhet.1903

U2 - 10.1002/jhet.1903

DO - 10.1002/jhet.1903

M3 - Article

SN - 1943-5193

VL - 51

JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

ER -

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

Abstract

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