Chemistry:Dicyanamide

From HandWiki

Dicyanamide, also known as dicyanamine, is an anion having the formula C2N3. It contains two cyanide groups bound to a central nitrogen anion. Dicyanamide is formed by decomposition of 2-cyanoguanidine. 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 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.[2]

Dean Kenyon examined the role of this chemical in reactions that can produce peptides,[3] and a co-worker examined dicyanamide's possible role in primordial biogenesis.[4]

References

  1. Shkrob, Ilya A.; Wishart, James F. (2012). "Free radical chemistry in room-temperature ionic liquids". Encyclopedia of Radicals in Chemistry, Biology and Materials. Wiley. doi:10.1002/9781119953678.rad013. 
  2. Kini, Aravinda M.; Geiser, Urs; Wang, Hau H.; Carlson, K. Douglas; Williams, Jack M.; Kwok, W. K.; Vandervoort, K. G.; Thompson, James E. et al. (1990). "A new ambient-pressure organic superconductor, κ-(ET)2Cu[N(CN)2]Br, with the highest transition temperature yet observed (inductive onset Tc= 11.6 K, resistive onset = 12.5 K)". Inorganic Chemistry 29 (14): 2555–2557. doi:10.1021/ic00339a004. 
  3. Steinman, G.; Kenyon, D. H.; Calvin, M. (1966). "The mechanism and protobiochemical relevance of dicyanamide-medicated peptide synthesis". Biochim Biophys Acta 124 (2): 339–350. doi:10.1016/0304-4165(66)90197-8. PMID 5968904. 
  4. Steinman, G.; Cole, M. N. (1967). "Synthesis of biologically pertinent peptides under possible primordial conditions". Proceedings of the National Academy of Sciences 58 (2): 735–742. doi:10.1073/pnas.58.2.735. PMID 5233470. Bibcode1967PNAS...58..735S.