Carbon nitride

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

Cyanogen is a carbon nitride.

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-C₃N₄, which is predicted to be harder than diamond.
• Graphitic carbon nitride - g-C₃N₄, with important catalytic and sensor properties.^[2]

• Dicyanodiazomethane (NC)₂C=N=N, the only C₃N₄ isomer studied experimentally
• Tricyanamide N(CN)₃ - C₃N₄ monomer (has never been prepared yet)
• Dicyanocarbodiimide NC−N=C=N−CN - another C₃N₄ monomer (was detected in products of photolysis of triazido-s-triazine).^[3]

• C₃N₅ - a combined triazole and triazine framework.^[4]
• MCN-12 (C₃N₆) and MCN-13 (C₃N₇).^[5]

Azafullerenes

• Azafullerenes are a class of heterofullerenes in which the element substituting for carbon is nitrogen.^[6] Examples include (C₅₉N)₂ (biazafullerenyl),^[7] 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 also called dicyano(diisocyano)methane
• hexacyanoethane - C₈N₆ or (N≡C−)₃C−C(−C≡N)₃
• hexacyanocyclopropane - C₉N₆ or cyclo-C₃(CN)₆
• hexacyanobutadiene^[8] - C₁₀N₆ or (N≡C−)₂C=C(−C≡N)−C(−C≡N)=C(−C≡N)₂

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) fits within this series.

• C₆N₂ or N≡C(−C≡C−)₂C≡N, dicyanobutadiyne or dicyanodiacetylene
• C₈N₂ or N≡C(−C≡C−)₃C≡N, dicyanohexatriyne or dicyanotriacetylene
• C₁₀N₂ or N≡C(−C≡C−)₄C≡N, dicyanooxatetrayne or dicyanotetraacetylene
• C₁₂N₂ or N≡C(−C≡C−)₅C≡N, dicyanodecapentayne or dicyanopentaacetylene
• C₁₄N₂ or N≡C(−C≡C−)₆C≡N, dicyanododecahexayne or dicyanohexaacetylene
• C₁₆N₂ or N≡C(−C≡C−)₇C≡N, dicyanotetradecaheptayne or dicyanoheptaacetylene
• C₁₈N₂ or N≡C(−C≡C−)₈C≡N, dicyanohexadecaoctayne or dicyanooctaacetylene
• C₂₀N₂ or N≡C(−C≡C−)₉C≡N, dicyanooctadecanonayne or dicyanononaacetylene
• C₂₂N₂ or N≡C(−C≡C−)₁₀C≡N, dicyanoicosadecayne or dicyanodecaacetylene

Perazidoalkynes, -alkenes and -alkanes

• tetraazidomethane - CN₁₂ or C(−N=N⁺=N⁻)₄

Percyanoheterocycles

• pentacyanopyridine - C₁₀N₆
• tetracyanopyrazine - C₈N₆
• tricyanotriazine - C₆N₆^[9]
• tetracyano-bitriazine - C₁₀N₁₀^[9]
• dicyanotetrazine - C₄N₆
• hexacyanotrisimidazole - C₁₅N₁₂
• hexacyanohexaazatriphenylene - C₁₈N₁₂

Aromatic cyanocarbons

• hexacyanobenzene - C₁₂N₆ or C₆(CN)₆
• octacyanonaphthalene - C₁₈N₈ or C₁₀(CN)₈
• decacyanoanthracene - C₂₄N₁₀ or C₁₄(CN)₁₀

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 C^II(−C≡N)₂ (and isomers cyanoisocyanocarbene ⁻C≡N⁺−C^II−C≡N, diisocyanocarbene ⁻C≡N⁺−C^II−⁺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 - C_nN⁻ (n odd)

See also

• Oxocarbon

References

1. 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.
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. 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.doi:10.1002/anie.200351879
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. doi:10.1002/anie.201811061
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. doi:10.1002/smll.201903572
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 Archived 2016-03-04 at the Wayback Machine
7. 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
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). doi:10.1021/JO025833H