Carbon_nitride

Carbon nitride

Carbon nitride

Chemical compound made of carbon and nitrogen

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]

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.[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

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    Vinodh, Rajangam; Atchudan, Raji; Yi, Moonsuk; Kim, Hee-Je (2022). "Synthesis and properties of carbon nitride materials". Nanostructured Carbon Nitrides for Sustainable Energy and Environmental Applications. pp. 1–18. doi:10.1016/B978-0-12-823961-2.00008-2. ISBN 978-0-12-823961-2.
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    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.
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    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. doi:10.1002/smll.201903572
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    D.J. Harris, Discovery of Nitroballs: Research in Fullerene Chemistry, 1993 California State Science Fair, http://www.usc.edu/CSSF/History/1993/S05.doc Archived 2016-03-04 at the Wayback Machine
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    Hummelen et al, "Isolation of the Heterofullerene C59N as Its Dimer (C59N)2", Science 269: 1554-1556 (1995). doi:10.1126/science.269.5230.1554
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    O.W.Webster, Hexacyanobutadiene, J. Am. Chem. Soc. 86(14): 2898–2902 (1964)
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    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). doi:10.1021/JO025833H
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