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diaminomaleonitrile
Sign in to saveAlso known as (2Z)-2,3-diaminobut-2-enedinitrile, DAMN
Diaminomaleonitrile (DAMN) is an organic compound composed of two amino groups and two nitrile groups bonded to a central alkene unit. The systematic name reflects its relationship to maleic acid. DAMN forms by oligomerization of hydrogen cyanide. It is the starting point for the synthesis of several classes of heterocyclic compounds. It has been considered as a possible organic chemical present in prebiotic conditions.
In the Vinony graph
Vinony's link graph records 11 inbound references to diaminomaleonitrile, and connects out to digital object identifier, chemical formula and International Standard Serial Number.
Vinony files it under Chembox image size set, Diamines and ECHA InfoCard ID from Wikidata.
Vinony links it to 6 Wikipedia language editions.
Chemical data
- Formula
- C4H4N4
- Molecular weight
- 108.1 g/mol
- IUPAC name
- (Z)-2,3-diaminobut-2-enedinitrile
- SMILES
- C(#N)/C(=C(\C#N)/N)/N
- InChIKey
- DPZSNGJNFHWQDC-ARJAWSKDSA-N
- XLogP
- -1
- Polar surface area
- 99.6 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- enamine
- Mass
- 108.04359612799999
Show 4 more facts
- isomeric SMILES
- C(#N)/C(=C(\C#N)/N)/N
- chemical formula
- C₄H₄N₄
- Commons category
- Diaminomaleonitrile
- canonical SMILES
- N#C/C(N)=C(/N)C#N
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- Isolation and synthesis
- Possible role in abiogenesis
- References
Diaminomaleonitrile (DAMN) is an organic compound composed of two amino groups and two nitrile groups bonded to a central alkene unit. The systematic name reflects its relationship to maleic acid. DAMN forms by oligomerization of hydrogen cyanide. It is the starting point for the synthesis of several classes of heterocyclic compounds. It has been considered as a possible organic chemical present in prebiotic conditions.
== Isolation and synthesis == Diaminomaleonitrile was first isolated in 1873 as an impure black solid, when it was recognized as a derivative of hydrogen cyanide with the formula (HCN)x. It was identified as the tetramer (HCN)4 by ebullioscopy in 1923. The cis-configuration of the amino groups was shown in 1928 through reaction with glyoxal to give , and the full structure was shown in 1955 to be diaminomaleonitrile, as opposed to the isomeric aminoiminosuccinonitrile (AISN). 282x282px It can be prepared by cyanation of aminomalononitrile.
Excerpted from Wikipedia’s “diaminomaleonitrile” article, available under the CC BY-SA 4.0 licence.