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cyanamide
Sign in to saveAlso known as Amidocyanogen, Carbimide, Carbodiimide, Cyanogen nitride, Hydrogen cyanamide, H2N-C#N, NH2CN, cyanoamine
Cyanamide is an organic compound with the formula CN2H2. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an alcohol-deterrent drug. One isomer of the molecule features a nitrile group attached to an amino group. Derivatives of this compound are also referred to as cyanamides, the most common being calcium cyanamide (CaCN2).
Chemical data
- Formula
- CH2N2
- Molecular weight
- 42.04 g/mol
- IUPAC name
- cyanamide
- SMILES
- C(#N)N
- InChIKey
- XZMCDFZZKTWFGF-UHFFFAOYSA-N
- XLogP
- -0.3
- Polar surface area
- 49.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
1,305 papers- Recent Advances in Cyanamide Chemistry: Synthesis and Applications.Molecules (Basel, Switzerland) · 2017
- Cyanamide-induced granulocytopenia.Internal medicine (Tokyo, Japan) · 1997
- [Cyanamide-ethanol reaction induced shock: report of a case and literature review].Chudoku kenkyu : Chudoku Kenkyukai jun kikanshi = The Japanese journal of toxicology · 2013
- Hydrogen cyanamide exposure: a case series from Pavia Poison Control Centre.Occupational medicine (Oxford, England) · 2023
- Cyanamide-induced aplastic anemia.European journal of clinical pharmacology · 2005
via PubMed
~8 min read
Encyclopedic overview
10 sectionsContents
- Tautomers and self-condensations
- Production
- Reactions and uses
- Agricultural use
- Environmental aspects
- Cyanamide functional group
- Cyanamide in space
- Safety
- References
- External links
Cyanamide is an organic compound with the formula CN2H2. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an alcohol-deterrent drug. One isomer of the molecule features a nitrile group attached to an amino group. Derivatives of this compound are also referred to as cyanamides, the most common being calcium cyanamide (CaCN2).
==Tautomers and self-condensations== Containing both a nucleophilic and electrophilic site within the same molecule, cyanamide undergoes various reactions with itself. Cyanamide exists as two tautomers, one with the connectivity N≡C–NH2 and the other with the formula HN=C=NH ("carbodiimide" tautomer). The N≡C–NH2 form dominates, but in a few reactions (e.g. silylation) the diimide form appears to be important.
Excerpted from Wikipedia’s “cyanamide” article, available under the CC BY-SA 4.0 licence.