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Not to be confused with Dicyandiamide.

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]

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 [wd] HN=C=N−C≡N, which is predicted to be slightly more stable than the symmetric tautomer dicyanimide [wd] 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]

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. p. 5. doi:10.1002/9781119953678.rad013.
  2. ^ Nichols, Charles M.; Wang, Zhe-Chen; Yang, Zhibo; Lineberger, W. Carl; Bierbaum, Veronica M. (25 February 2016). “Experimental and Theoretical Studies of the Reactivity and Thermochemistry of Dicyanamide: N(CN)2–“. The Journal of Physical Chemistry A. 120 (7): 992–999. doi:10.1021/acs.jpca.5b12496.
  3. ^ Kini, Aravinda M.; Geiser, Urs; Wang, Hau H.; Carlson, K. Douglas; Williams, Jack M.; Kwok, W. K.; Vandervoort, K. G.; Thompson, James E.; Stupka, Daniel L. (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.
  4. ^ 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.
  5. ^ 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. Bibcode:1967PNAS…58..735S. doi:10.1073/pnas.58.2.735. PMC 335695. PMID 5233470.