Carbon nitride explained

Carbon nitrides are organic compounds consisting only of carbon and nitrogen atoms.

Covalent network compounds

These materials are organic semiconductors. 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]

• Beta carbon nitride - a solid with a formula β-, which is predicted to be harder than diamond.
• Graphitic carbon nitride - g-, with important catalytic and sensor properties.^[2]
• Dicyanodiazomethane =N=N, the only isomer studied experimentally
• Tricyanamide - monomer (has never been prepared yet)
• Dicyanocarbodiimide NC-N=C=N-CN - another monomer (was detected in products of photolysis of triazido-s-triazine).^[3]
• - a combined triazole and triazine framework.^[4]
• MCN-12 and MCN-13 .^[5]

Azafullerenes

• Azafullerenes are a class of heterofullerenes in which the element substituting for carbon is nitrogen.^[6] Examples include (biazafullerenyl),^[7] (diaza[60]fullerene), (triaza[60]fullerene) and .

Cyanofullerenes

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

Cyanogen

• Cyanogen -
• Isocyanogen -
• Diisocyanogen -
• Paracyanogen - a cyanogen polymer,
• Paraisocyanogen - a cyanogen polymer,

Percyanoalkynes, -alkenes and -alkanes

• dicyanoacetylene - or, also called carbon subnitride or but-2-ynedinitrile
• tetracyanoethylene - or
• tetracyanomethane - or
• 2,2-diisocyanopropanedinitrile - or also called dicyano(diisocyano)methane
• hexacyanoethane - or
• hexacyanocyclopropane - or cyclo-
• hexacyanobutadiene^[8] - or

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 fits within this series.

• or, dicyanobutadiyne or dicyanodiacetylene
• or, dicyanohexatriyne or dicyanotriacetylene
• or, dicyanooxatetrayne or dicyanotetraacetylene
• or, dicyanodecapentayne or dicyanopentaacetylene
• or, dicyanododecahexayne or dicyanohexaacetylene
• or, dicyanotetradecaheptayne or dicyanoheptaacetylene
• or, dicyanohexadecaoctayne or dicyanooctaacetylene
• or, dicyanooctadecanonayne or dicyanononaacetylene
• or, dicyanoicosadecayne or dicyanodecaacetylene

Perazidoalkynes, -alkenes and -alkanes

• tetraazidomethane - or

Percyanoheterocycles

• pentacyanopyridine -
• tetracyanopyrazine -
• tricyanotriazine - ^[9]
• tetracyano-bitriazine - ^[9]
• dicyanotetrazine -
• hexacyanotrisimidazole -
• hexacyanohexaazatriphenylene -

Aromatic cyanocarbons

• hexacyanobenzene - or
• octacyanonaphthalene - or
• decacyanoanthracene - or

Other compounds

• cyanonitrene - or (one of the nitrogens is univalent)
• azodicarbonitrile - or, cis and trans isomers
• cyanogen azide - or
• 1-diazidocarbamoyl-5-azidotetrazole -
• 2,2′-azobis(5-azidotetrazole) -
• triazidotriazine (cyanuric triazide) -
• triazidoheptazine -
• tricyanomethanimine (dicyanomethylene-cyanamide) - or
• diazidodicyanoethylene - or and, cis and trans
• dicyanodiazomethane - or
• - or (and isomers cyanoisocyanocarbene, diisocyanocarbene, 3-cyano-2H-azirenylidene and 3-isocyano-2H-azirenylidene)
• 1,3,5-triazido-2,4,6-tricyanobenzene -
• nitrogen tricyanide and carbon bis(cyanamide), two formal monomers of polymeric

Anions and functional groups

• cyanide - ion, cyanide and isocyanide functional groups
• dicyanamide - or
• tricyanomethanide - or
• pentacyanoethanide - or
• pentacyanopropenide (pentacyanoallyl anion) -
• 2-dicyanomethylene-1,1,3,3-tetracyanopropanediide
• tricyanomelaminate anion -
• melonate -
• anions - (n odd) and (n even)
• cyanoacetlyide - or
• cyanobutadiynylide - or
• cyanopolyynide anions - (n odd)

See also

• Oxocarbon

Notes and References

1. Book: Vinodh, Rajangam . Nanostructured Carbon Nitrides for Sustainable Energy and Environmental Applications . Atchudan . Raji . Yi . Moonsuk . Kim . Hee-Je . 2022 . 978-0-12-823961-2 . 1–18 . Synthesis and properties of carbon nitride materials . 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 . 10.1016/j.snb.2017.10.053 . free.
3. Sato, T., Narazaki, A., Kawaguchi, Y., Niino, H. and Bucher, G. (2003), Dicyanocarbodiimide and Trinitreno-s-triazine Generated by Consecutive Photolysis of Triazido-s-triazine in a Low-Temperature Nitrogen Matrix†. Angewandte Chemie International Edition, 42: 5206-5209.
4. 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.
5. 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.
6. D.J. Harris, Discovery of Nitroballs: Research in Fullerene Chemistry, 1993 California State Science Fair, http://www.usc.edu/CSSF/History/1993/S05.html
7. Hummelen et al, "Isolation of the Heterofullerene C59N as Its Dimer (C59N)2", Science 269: 1554-1556 (1995).
8. O.W.Webster, Hexacyanobutadiene, J. Am. Chem. Soc. 86(14): 2898–2902 (1964)
9. 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).