Cyanogen is a carbon nitride.

In organic chemistry, carbon nitrides are compounds consisting only of carbon and nitrogen atoms. Carbon nitrides are also known as organic semiconductors with a band gap of 2.7 eV. Due to its hydrogen-bonding motifs and electron-rich properties, this carbon material is considered a potential candidate for material applications in carbon supplementation. [1]

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.[2]
  • C3N5 - a combined triazole and triazine framework.[3]
  • MCN-12 (C3N6) and MCN-13 (C3N7).[4]

Azafullerenes

  • Azafullerenes are a class of heterofullerenes in which the element substituting for carbon is nitrogen.[5] Examples include (C59N)2 (biazafullerenyl),[6] 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 (N≡C−C≡N)
  • Isocyanogen - C2N2 (−C≡N+−C≡N)
  • Diisocyanogen - C2N2 (−C≡N+−+N≡C−)
  • Paracyanogen - a cyanogen polymer, (NCCN)n
  • Paraisocyanogen - a cyanogen polymer, (CNCN)n

Percyanoalkynes, -alkenes and -alkanes

  • dicyanoacetylene - C4N2 or N≡C−C≡C−C≡N, also called carbon subnitride or but-2-ynedinitrile
  • tetracyanoethylene - C6N4 or (N≡C−)2C=C(−C≡N)2
  • tetracyanomethane - C5N4 or C(−C≡N)4
  • 2,2-diisocyanopropanedinitrile - C5N4 or (−C≡N+−)2C(−C≡N)2
  • hexacyanoethane - C8N6 or (N≡C−)3C−C(−C≡N)3
  • hexacyanocyclopropane - C9N6 or C3(CN)6
  • hexacyanobutadiene[7] - C10N6 or 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 (N≡C−C≡C−C≡N) otherwise fits within this series.

  • C6N2 or N≡C−C≡C−C≡C−C≡N, dicyanobutadiyne (dicyanodiacetylene)
  • C8N2 or N≡C−C≡C−C≡C−C≡C−C≡N, dicyanohexatriyne
  • C10N2 or N≡C−C≡C−C≡C−C≡C−C≡C−C≡N
  • C12N2 or N≡C−C≡C−C≡C−C≡C−C≡C−C≡C−C≡N
  • C14N2 or N≡C−C≡C−C≡C−C≡C−C≡C−C≡C−C≡C−C≡N
  • C16N2 or N≡C−C≡C−C≡C−C≡C−C≡C−C≡C−C≡C−C≡C−C≡N
  • C18N2 or N≡C−C≡C−C≡C−C≡C−C≡C−C≡C−C≡C−C≡C−C≡C−C≡N
  • C20N2 or N≡C−C≡C−C≡C−C≡C−C≡C−C≡C−C≡C−C≡C−C≡C−C≡C−C≡N
  • C22N2 or N≡C−C≡C−C≡C−C≡C−C≡C−C≡C−C≡C−C≡C−C≡C−C≡C−C≡C−C≡N

Perazidoalkynes, -alkenes and -alkanes

Percyanoheterocycles

Aromatic cyanocarbons

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

Other compounds

  • cyanonitrene - CN2 or [N≡C−N ⇌ −N=C=N+ ⇌ +N=C=N− ⇌ N−C≡N] (one of the nitrogens is univalent)
  • azodicarbonitrile - C2N4 or N≡C−N=N−C≡N, cis and trans isomers
  • cyanogen azide - CN4 or N≡C−N=N+=N−
  • 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 or N≡C−N=C(−C≡N)2
  • diazidodicyanoethylene - C4N8 or (−N=N+=N−)2C=C(−C≡N)2 and (−N=N+=N−)(N≡C−)C=C(−N=N+=N−)(−C≡N), cis and trans
  • dicyanodiazomethane - C3N4 or (N≡C−)2C=N+=N−
  • dicyanocarbene - C3N2 or CII(−C≡N)2 (and isomers cyanoisocyanocarbene −C≡N+−CII−C≡N, diisocyanocarbene −C≡N+−CII−+N≡C−, 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(−C≡N)3 and carbon bis(cyanamide) N≡C−N=C=N−C≡N, two formal monomers of polymeric C3N4

Anions and functional groups

  • cyanide - −C≡N ion, cyanide −C≡N and isocyanide −+N≡C− functional groups
  • dicyanamide - N(CN)−2 or −N(−C≡N)2
  • tricyanomethanide - C(CN)−3 or −C(−C≡N)3
  • pentacyanoethanide - C2(CN)−5 or (N≡C−)2C−−C(−C≡N)3
  • 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− or −C≡C−C≡N
  • cyanobutadiynylide - C5N− or −C≡C−C≡C−C≡N
  • cyanopolyynide anions - CnN− (n odd)

See also

References

  1. ↑ https://doi.org/10.1016/B978-0-12-823961-2.00008-2
  2. ↑ 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.
  3. ↑ I. Y. Kim, S. Kim, X. Jin, S. Premkumar, G. Chandra, N.-S. Lee, G. P. Mane, S.-J. Hwang, S. Umapathy, A. Vinu, Angew. Chem. Int. Ed. 2018, 57, 17135.
  4. ↑ Kim, I. Y., Kim, S., Premkumar, S., Yang, J.-H., Umapathy, S., Vinu, A., Thermodynamically Stable Mesoporous C3N7 and C3N6 with Ordered Structure and Their Excellent Performance for Oxygen Reduction Reaction. Small 2020, 16, 1903572.
  5. ↑ D.J. Harris, Discovery of Nitroballs: Research in Fullerene Chemistry, 1993 California State Science Fair, http://www.usc.edu/CSSF/History/1993/S05.html Archived 2016-03-04 at the Wayback Machine
  6. ↑ Hummelen et al, Isolation of the Heterofullerene C59N as Its Dimer (C59N)2, Science 269: 1554-1556 (1995)
  7. ↑ O.W.Webster, Hexacyanobutadiene, J. Am. Chem. Soc. 86(14): 2898–2902 (1964)
  8. 1 2 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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