2-Hydroxymethylamino-4-thiazolinone. Confirmation and chelate formation
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In DMSO-d6 solution 2-hydroxymethylamino-4-thiazolinone, as well as its 5-methylcongener, 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.
KeywordsOxygen Hydrogen Hydrogen Bond Organic Chemistry Oxygen Atom
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