dicyanamide

{{Distinguish|Dicyandiamide}}

{{Chembox

| ImageFile = Dicyanamide.png

| ImageCaption = Structure of dicyanamide

|Section1={{Chembox Identifiers

| ChemSpiderID = 3786559

| PubChem = 4594639

| StdInChI=1S/C2N3/c3-1-5-2-4/q-1

| StdInChIKey = UKDLHLAPDXIAID-UHFFFAOYSA-N

| SMILES = C(=[N-])=NC#N

}}

|Section2={{Chembox Properties

| C=2|N=3|Formula_Charge = −

}}

|Section8={{Chembox Related

}}

}}

Dicyanamide, also known as dicyanamine, is an anion having the formula {{chem|C|2|N|3|−}}. It contains two cyanide groups bound to a central nitrogen anion. The chemical is formed by decomposition of 2-cyanoguanidine. It is used extensively as a counterion of organic and inorganic salts, and also as a reactant for the synthesis of various covalent organic structures.

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.{{cite journal |doi= 10.1021/ic00339a004 |title= A new ambient-pressure organic superconductor, κ-(ET)₂Cu[N(CN)₂]Br, with the highest transition temperature yet observed (inductive onset T_c= 11.6 K, resistive onset = 12.5 K) |first1= Aravinda M. |last1= Kini |first2= Urs |last2= Geiser |first3= Hau H. |last3= Wang |first4= K. Douglas |last4= Carlson |first5= Jack M. |last5= Williams |first6= W. K. |last6= Kwok |first7= K. G. |last7= Vandervoort |first8= James E. |last8= Thompson |first9= Daniel L. |last9= Stupka |journal= Inorganic Chemistry |year= 1990 |volume= 29 |issue = 14|pages= 2555–2557}} Dean Kenyon has examined the role of this chemical in reactions that can produce peptides.{{cite journal |last1= Steinman |first1= G. |last2= Kenyon |first2= D. H. |authorlink2= Dean H. Kenyon |last3= Calvin |first3= M. |title= The mechanism and protobiochemical relevance of dicyanamide-medicated peptide synthesis |journal= Biochim Biophys Acta |year= 1966 |volume= 124 |issue= 2 |pages= 339–350 |pmid= 5968904 |doi=10.1016/0304-4165(66)90197-8}} A co-worker then considered this reactive nature and examined the possible role dicyanamide may have had in primordial biogenesis.{{cite journal |journal= Proceedings of the National Academy of Sciences |year= 1967 |volume= 58 |issue= 2 |pages= 735–742 |title= Synthesis of biologically pertinent peptides under possible primordial conditions |last1= Steinman |first1= G. |last2= Cole |first2= M. N. |pmid= 5233470 |doi=10.1073/pnas.58.2.735 |pmc=335695|doi-access= free |bibcode= 1967PNAS...58..735S }}