Dicyanamide
Chemical compound
From Wikipedia, the free encyclopedia
Dicyanamide (abbreviated as dca when a ligand) is an anion with the formula C2N−3. It contains two cyanide groups bound to a central nitrogen anion. Dicyanamide is formed by decomposition of 2-cyanoguanidine.[citation needed]
Structure of dicyanamide | |
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3D model (JSmol) |
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PubChem CID |
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| Properties | |
| C2N3− | |
| Molar mass | 66.044 g·mol−1 |
| Conjugate acid | Dicyanamine (Hdca) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dicyanamide is used extensively as a counterion of organic and inorganic salts, as it is a "chemically inert, hydrophobic anion" and pseudohalide.[1] It is also as a reactant for the synthesis of various covalent organic structures.
Dicyanamide has a very low proton affinity, less than 310 ± 3 kcal·mol−1. Its gas-phase conjugate acid is iminomethylidenecyanamide HN=C=N−C≡N, which is predicted to be slightly more stable than the symmetric tautomer dicyanimide N≡C−NH−C≡N.[2]
Dicyanamide was used as an anionic component in an organic superconductor that was, when reported in 1990, a superconductor with the highest transition temperature in its structural class.[3]
Dean Kenyon examined the role of this chemical in reactions that can produce peptides,[4] and a co-worker examined dicyanamide's possible role in primordial biogenesis.[5]