Carbamic acid

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Carbamic acid
Structural formula of carbamic acid Ball-and-stick model of carbamic acid
Identifiers
CAS number 463-77-4 YesY
PubChem 277
ChemSpider 271 YesY
DrugBank DB04261
KEGG C01563 YesY
MeSH Carbamic+acid
ChEBI CHEBI:28616 YesY
ChEMBL CHEMBL125278 YesY
Jmol-3D images Image 1
Properties
Molecular formula CH3NO2
Molar mass 61.040 g/mol
Related compounds
Related compounds Formamide
Dithiocarbamate
Carbonic acid
Urea
Ethyl carbamate
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Carbamic acid is the compound with the formula H2NCO2H. The attachment of the acid group to an nitrogen or amine (instead of carbon) distinguishes it from carboxylic acid and an amide. Many derivatives and analogues of carbamic acid are known. They are generally unstable, reverting to the parent amine and carbon dioxide.[1] The deprotonated anion (or conjugate base) of this functional group is a carbamate. Carbamic acid is a planar molecule.[2]

Occurrence[edit]

Carbamic acid is an intermediate in the production of urea, which involves the reaction of carbon dioxide and ammonia.[3]

CO2 + NH3 → H2N-CO2H
H2N-CO2H + NH3 → CO(NH2)2 + H2O

"Carbamoyltransferases" are transferase enzymes classified under EC number 2.1.3.

Derivatives of carbamic acid[edit]

Carbamic acids are intermediates in the decomposition of carbamate protecting groups; the hydrolysis of an ester bond produces carbamic acid the evolution of carbon dioxide drives the deprotection reaction forward, yielding the unprotected amine.

Carbamates usually refer to esters of carbamic acid. Methyl carbamate is the simplest ester of carbamic acid. Unlike carbamic acids, the esters are stable. They are prepared by reaction of carbamoyl chlorides with alcohols, the addition of alcohols to isocyanates, and the reaction of carbonate esters with ammonia.[4]

Some esters have use as muscle relaxants,[5] while others are used as insecticides, for example aldicarb.[6]

See also[edit]

References[edit]

  1. ^ Thomas L. Lemke. (2003). Review of organic functional groups : introduction to medicinal organic chemistry. Philadelphia, Pa.: Lippincott Williams & Wilkins. p. 63. ISBN 978-0-7817-4381-5. 
  2. ^ R.K. Khanna, M.H. Moore. (1998). "A 55". Carbamic acid: molecular structure and IR spectra (pii: S1386-1425(98)00228-5). Greenbelt, MD.: Elsevier. pp. 961–967. 
  3. ^ Meessen, J. H.; Petersen, H. (2005), "Urea", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a27_333 
  4. ^ Peter Jäger, Costin N. Rentzea and Heinz Kieczka "Carbamates and Carbamoyl Chlorides" in Ullmann's Encyclopedia of Industrial Chemistry, 2012, Wiley-VCH, Weinheim. doi:10.1002/14356007.a05_051
  5. ^ ed. by John H. Block, John M. Beale. (2004). "Central Nervous System Depressant". Wilson and Gisvold's textbook of organic medicinal and pharmaceutical chemistry. Philadelphia, Pa.: Lippincott Williams & Wilkins. p. 495. ISBN 978-0-7817-3481-3. 
  6. ^ Risher, JF; Mink, FL; Stara, JF (1987). "The toxicologic effects of the carbamate insecticide aldicarb in mammals: a review". Environmental health perspectives 72: 267–81. doi:10.2307/3430304. JSTOR 3430304. PMC 1474664. PMID 3304999.