Are you an EPFL student looking for a semester project?
Work with us on data science and visualisation projects, and deploy your project as an app on top of Graph Search.
Concept
Carbamate
Summary
In organic chemistry, a carbamate is a category of organic compounds with the general formula and structure , which are formally derived from carbamic acid (). The term includes organic compounds (e.g., the ester ethyl carbamate), formally obtained by replacing one or more of the hydrogen atoms by other organic functional groups; as well as salts with the carbamate anion (e.g. ammonium carbamate).
Polymers whose repeat units are joined by carbamate like groups are an important family of plastics, the polyurethanes. See Etymology for clarification.
While carbamic acids are unstable, many carbamate esters and salts are stable and well known.
In water solutions, the carbamate anion slowly equilibrates with the ammonium NH4+ cation and the carbonate CO32- or bicarbonate HCO3- anions:
Calcium carbamate is soluble in water, whereas calcium carbonate is not. Adding a calcium salt to an ammonium carbamate/carbonate solution will precipitate some calcium carbonate immediately, and then slowly precipitate more as the carbamate hydrolyzes.
The salt ammonium carbamate is generated by treatment of ammonia with carbon dioxide:
2 NH3 + CO2 → NH4[H2NCO2]
Carbamate esters also arise via alcoholysis of carbamoyl chlorides:
R2NC(O)Cl + R'OH → R2NCO2R' + HCl
Alternatively, carbamates can be formed from chloroformates and amines:
R'OC(O)Cl + R2NH → R2NCO2R' + HCl
Carbamates may be formed from the Curtius rearrangement, where isocyanates formed are reacted with an alcohol.
RCON3 → RNCO + N2
RNCO + R′OH → RNHCO2R′
Within nature carbon dioxide can bind with neutral amine groups to form a carbamate, this post-translational modification is known as carbamylation. This modification is known to occur on several important proteins; see examples below.
The N-terminal amino groups of valine residues in the α- and β-chains of deoxyhemoglobin exist as carbamates. They help to stabilise the protein when it becomes deoxyhemoglobin, and increases the likelihood of the release of remaining oxygen molecules bound to the protein.
Official source
About this result
This page is automatically generated and may contain information that is not correct, complete, up-to-date, or relevant to your search query. The same applies to every other page on this website. Please make sure to verify the information with EPFL's official sources.