Open AccessSolid‐State‐Trapped Reactive Ammonium Carbamate Self‐Derivative Salts of Prolinamide
Author(s) -
Tilborg Anaëlle,
Lanners Steve,
Norberg Bernadette,
Wouters Johan
Publication year - 2013
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201300025
Subject(s) - chemistry , carbamate , reactivity (psychology) , salt (chemistry) , sublimation (psychology) , hydrogen bond , molecule , ammonium , derivative (finance) , adduct , solid state , zwitterion , organic chemistry , polymer chemistry , inorganic chemistry , pathology , financial economics , economics , psychotherapist , medicine , psychology , alternative medicine
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.