2-HYDROXYMETHYLAMINO-4-THIAZOLINONE. CONFIRMATION AND CHELATE FORMATION

Article abstract of DOI:10.1007/BF00519539

In DMSO-d₆ solution 2-hydroxymethylamino-4-thiazolinone, as well as its 5-methyl-congener, exists in the form of E- and Z-conformers relative to the exocyclic nitrogen-carbon bond; for each of these conformers, furthermore, both a transoid and cisoid orientation of the hydrogen and oxygen atoms, relative to the N-CH₂ bond, are possible.The transoid form is able to form a chelate derivative with intramolecular hydrogen bond formation.Both acids and bases catalyze transitions among the "open" forms, although chelate formation is only acid-catalyzed.