Solid-state-trapped reactive ammonium carbamate self-derivative salts of prolinamide

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Résumé

Single crystals for two polymorphs of the ammonium carbamate self-derivative salt of prolinamide have been successfully obtained and characterized. Decarbonation of the carbamate salts was monitored by calorimetry, confirming stabilization of the reactive carbonated adducts in the solid state. Sublimation of the salts afforded crystals of prolinamide, leading to the first crystal structure of this otherwise common molecule. Reactivity of the ammonium carbamate self-derivative salt is further illustrated by the observation of a series of derived products, including dehydroprolinamide, a methylene-bridged prolinamide, and a bicyclic derivative. Crystal structures of these products display distinct amidic and/or non-amidic hydrogen bonding. This study emphasizes the reactivity of carbonated amines stabilized in the solid and opens perspectives for a systematic study of (solid-state) reactions involving these trapped reactive species.
langue originaleAnglais
Pages (de - à)194-199
Nombre de pages6
journalChemistryOPEN
Volume2
Numéro de publication5-6
Date de mise en ligne précoce12 août 2013
Les DOIs
Etat de la publicationPublié - 1 déc. 2013

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