title: Solid-state-trapped reactive ammonium carbamate self-derivative salts of prolinamide.
abstract: 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.
authors.affiliation: Chemistry Department, University of Namur Rue de Bruxelles 61, 5000 Namur (Belgium) E-mail: johan.wouters@unamur.be.
authors.forename: Anaëlle
authors.initials: A
authors.lastname: Tilborg
authors.affiliation: Chemistry Department, University of Namur Rue de Bruxelles 61, 5000 Namur (Belgium) E-mail: johan.wouters@unamur.be.
authors.forename: Steve
authors.initials: S
authors.lastname: Lanners
authors.affiliation: Chemistry Department, University of Namur Rue de Bruxelles 61, 5000 Namur (Belgium) E-mail: johan.wouters@unamur.be.
authors.forename: Bernadette
authors.initials: B
authors.lastname: Norberg
authors.affiliation: Chemistry Department, University of Namur Rue de Bruxelles 61, 5000 Namur (Belgium) E-mail: johan.wouters@unamur.be.
authors.forename: Johan
authors.initials: J
authors.lastname: Wouters
keywords: ammonium carbamate self-derivative salts; cocrystals; crystal structure determination; prolinamides; reactive species