Solid-State-Trapped Reactive Ammonium Carbamate Self-Derivative Salts of Prolinamide
Article first published online: 12 AUG 2013
© 2013 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.
Volume 2, Issue 5-6, pages 194–199, December 2013
How to Cite
Tilborg, A., Lanners, S., Norberg, B. and Wouters, J. (2013), Solid-State-Trapped Reactive Ammonium Carbamate Self-Derivative Salts of Prolinamide. ChemistryOpen, 2: 194–199. doi: 10.1002/open.201300025
- Issue published online: 19 DEC 2013
- Article first published online: 12 AUG 2013
- Manuscript Received: 30 MAY 2013
- Funded Access
- Fonds pour la formation à la Recherche dans l′Industrie et dans l′Agriculture (FRIA)
- Fonds National de la Recherche Scientifique (FNRS). Grant Number: 2.4511.07
- crystal structure determination;
- reactive species;
- ammonium carbamate self-derivative salts
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.