Carbon nitride

In organic chemistry, carbon nitrides are compounds consisting only of carbon and nitrogen atoms.

Cyanogen is a carbon nitride.

Covalent network compounds
  • Beta carbon nitride - a solid with a formula β-C3N4, which is predicted to be harder than diamond.
  • Graphitic carbon nitride - g-C3N4, with important catalytic and sensor properties.[1]

Azafullerenes
  • Azafullerenes are a class of heterofullerenes in which the element substituting for carbon is nitrogen.[2] Examples include (C59N)2 (biazafullerenyl),[3] C58N2 (diaza[60]fullerene), C57N3 (triaza[60]fullerene) and C48N12.

Cyanofullerenes
  • Cyanofullerenes are a class of modified fullerenes in which cyano- groups are attached to a fullerene skeleton. These have the formula C60(CN)2n, where n takes the values 1 to 9.

Cyanogen
  • Cyanogen - C2N2 (NCCN)
  • Isocyanogen - C2N2 (CNCN)
  • Diisocyanogen - C2N2 (CNNC)
  • Paracyanogen - a cyanogen polymer, (NCCN)n
  • Paraisocyanogen - a cyanogen polymer, (CNCN)n

Percyanoalkynes, -alkenes and -alkanes
  • dicyanoacetylene - C4N2 (C2(CN)2), also called carbon subnitride or but-2-ynedinitrile
  • tetracyanoethylene - C6N4 (C2(CN)4)
  • tetracyanomethane - C5N4 (C(CN)4)
  • 2,2-diisocyanopropanedinitrile - C5N4 (C(CN)2(NC)2)
  • hexacyanoethane - C8N6 (C2(CN)6)
  • hexacyanocyclopropane - C9N6 (C3(CN)6)
  • hexacyanobutadiene[4] - C10N6 (C4(CN)6)

Dicyanopolyynes

Dicyanopolyynes are composed of a chain of carbon atoms with alternating single and triple bonds, terminated by nitrogen atoms. Although not a polyyne dicyanoacetylene otherwise fits within this series.

  • dicyanobutadiyne (dicyanodiacetylene) - C6N2
  • dicyanohexatriyne - C8N2
  • C10N2
  • C12N2
  • C14N2
  • C16N2
  • C18N2
  • C20N2
  • C22N2

Perazidoalkynes, -alkenes and -alkanes

Percyanoheterocycles

Aromatic cyanocarbons
  • hexacyanobenzene - C12N6
  • octacyanonaphthalene - C18N8
  • decacyanoanthracene - C24N10

Other compounds
  • cyanonitrene - CN2 (NCN)
  • azodicarbonitrile - C2N4 ((NCN)2)
  • cyanogen azide - CN4 (NC.N3)
  • 1-diazidocarbamoyl-5-azidotetrazole - C2N14
  • 2,2′-azobis(5-azidotetrazole) - C2N16
  • triazidotriazine (cyanuric triazide) - C3N12 (C3N3(N3)3)
  • triazidoheptazine - C6N16 (C6N7(N3)3)
  • tricyanomethanimine (Dicyanomethylene-cyanamide) - C4N4 ((CN).N.C(CN)2)
  • diazidodicyanoethylene - C4N8 ((N3)2.C.C(CN)2)
  • dicyanodiazomethane - C3N4 ((CN)2.C.N2)
  • dicyanocarbene - C3N2 (and isomers cyanoisocyanocarbene, diisocyanocarbene, 3-cyano-2H-azirenylidene and 3-isocyano-2H-azirenylidene)
  • 1,3,5-triazido-2,4,6-tricyanobenzene - C9N12 (C6(CN)3(N3)3)
  • nitrogen tricyanide N(CN)3 and carbon bis(cyanamide) NCN=C=NCN, two formal monomers of polymeric C3N4

Anions
  • cyanide and isocyanide - CN− and NC−
  • dicyanamide - N(CN)−2
  • tricyanomethanide - C(CN)−3
  • pentacyanoethanide - C2(CN)−5
  • pentacyanopropenide (pentacyanoallyl anion) - C3(CN)−5
  • 2-dicyanomethylene-1,1,3,3-tetracyanopropanediide C10N2−6
  • tricyanomelaminate anion - C3N3(NCN)3−3
  • melonate - C6N7(NCN)3−3
  • cyanofullerene anions - C60(CN)n− (n odd) and C60(CN)n2− (n even)
  • cyanoacetlyide - C3N−
  • cyanobutadiynylide - C5N−
  • cyanopolyynide anions - CnN− (n odd)

See also

References
  1. Lv, Hongying; Teng, Zhenyuan; Wang, Sicong; Feng, Ke; Wang, Xiaoli; Wang, Chengyin; Wang, Guoxiu (March 2018). "Voltammetric simultaneous ion flux measurements platform for Cu2+, Pb2+ and Hg2+ near rice root surface: Utilizing carbon nitride heterojunction film modified carbon fiber microelectrode". Sensors and Actuators B: Chemical. 256: 98–106. doi:10.1016/j.snb.2017.10.053.
  2. D.J. Harris, Discovery of Nitroballs: Research in Fullerene Chemistry, 1993 California State Science Fair, http://www.usc.edu/CSSF/History/1993/S05.html
  3. Hummelen et al, Isolation of the Heterofullerene C59N as Its Dimer (C59N)2, Science 269: 1554-1556 (1995)
  4. O.W.Webster, Hexacyanobutadiene, J. Am. Chem. Soc. 86(14): 2898–2902 (1964)
  5. Sesto et al, Chemical Reduction of 2,4,6-Tricyano-1,3,5-triazine and 1,3,5-Tricyanobenzene. Formation of Novel 4,4',6,6'-Tetracyano-2,2'-bitriazine and Its Radical Anion, J. Org. Chem. 68: 3367-3379 (2003)
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