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.
Original languageEnglish
Pages (from-to)194-199
Number of pages6
JournalChemistryOPEN
Volume2
Issue number5-6
Early online date12 Aug 2013
DOIs
Publication statusPublished - 1 Dec 2013

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Salts
Derivatives
Crystal structure
Carbamates
Sublimation
Calorimetry
Polymorphism
Solid state reactions
Amines
Hydrogen bonds
Stabilization
Single crystals
Crystals
Molecules
carbamic acid
prolinamide

Keywords

  • Ammonium carbamate self-derivative salts
  • Cocrystals
  • Crystal structure determination
  • Prolinamides
  • Reactive species

Cite this

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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.",
keywords = "Ammonium carbamate self-derivative salts, Cocrystals, Crystal structure determination, Prolinamides, Reactive species",
author = "Ana{\"e}lle Tilborg and Steve Lanners and Bernadette Norberg and Johan Wouters",
year = "2013",
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TY - JOUR

T1 - Solid-state-trapped reactive ammonium carbamate self-derivative salts of prolinamide

AU - Tilborg, Anaëlle

AU - Lanners, Steve

AU - Norberg, Bernadette

AU - Wouters, Johan

PY - 2013/12/1

Y1 - 2013/12/1

N2 - 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.

AB - 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.

KW - Ammonium carbamate self-derivative salts

KW - Cocrystals

KW - Crystal structure determination

KW - Prolinamides

KW - Reactive species

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