Premium
Synthesis, spectroscopic, theoretical and structural studies of new trihalomethyl sulphenyl derivatives of 5‐methyl‐1,3,4‐thiadiazole‐2‐thiol
Author(s) -
Coyanis E. M.,
Boese R.,
Autino J. C.,
Romano R. M.,
Della Védova C. O.
Publication year - 2003
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.553
Subject(s) - tautomer , chemistry , moiety , thiol , electrophile , reactivity (psychology) , density functional theory , computational chemistry , raman spectroscopy , sulfur , mass spectrometry , medicinal chemistry , substitution reaction , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , medicine , physics , alternative medicine , pathology , chromatography , optics
Although 2‐mercapto‐5‐methyl‐1,3,4‐thiadiazole (mmtd) is commonly thought of as a thione tautomer, electrophilic substitution occurs on the thiol moiety. The tautomeric ability of mmtd allows a substitution reaction to take place at the sulphur; this is shown by reaction with Cl 3− n F n CSCI compounds ( n = 0–2) to give perhalomethyldithio thiadiazole derivatives. Three novel perhalomethylsulphenyl compounds, which exhibit a wide range of potentially interesting applications, were obtained and characterized by x‐ray crystal diffraction, mass spectrometry, IR and Raman spectroscopy and density functional theory calculations. Copyright © 2002 John Wiley & Sons, Ltd.