Carbon nitride

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

• 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 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 – 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

• 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^[7] – C₁₀N₆ or (N≡C−)₂C=C(−C≡N)−C(−C≡N)=C(−C≡N)₂

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

• pentacyanopyridine – C₁₀N₆
• tetracyanopyrazine – C₈N₆
• tricyanotriazine – C₆N₆^[8]
• tetracyano-bitriazine – C₁₀N₁₀^[8]
• dicyanotetrazine – C₄N₆
• hexacyanotrisimidazole – C₁₅N₁₂
• hexacyanohexaazatriphenylene – C₁₈N₁₂

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

• cyanonitrene – CN₂ or [N≡C−N ⇌ ⁻N=C=N⁺ ⇌ ⁺N=C=N⁻ ⇌ N−C≡N] (one of the nitrogens is univalent)
• azodicarbonitrile [de] – 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) [wd] – C₂N₁₆
• dicyanocarbene^[9] – 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)
• dicyanodiazomethane^[10] – C₃N₄ or (N≡C−)₂C=N⁺=N⁻, the only C₃N₄ isomer prepared in bulk
• tricyanamide (nitrogen tricyanide) – C₃N₄ or N(−C≡N)₃, has never been prepared yet
• dicyanocarbodiimide (carbon bis(cyanamide)) – C₃N₄ or N≡C−N=C=N−C≡N, detected in photolysis products of triazido-s-triazine^[11]
• cyanuric triazide (triazido-s-triazine) – C₃N₁₂ or C₃N₃(N₃)₃
• dicyanomethylenecyanamide [wd] (tricyanomethanimine)^[12] – C₄N₄ or N≡C−N=C(−C≡N)₂
• diazidodicyanoethylene – C₄N₈ or (⁻N=N⁺=N−)₂C=C(−C≡N)₂^[12]: 1235 and (⁻N=N⁺=N−)(N≡C−)C=C(−N=N⁺=N⁻)(−C≡N), cis and trans
• 2,5,8-triazido-s-heptazine^[13] – C₆N₁₆ (C₆N₇(N₃)₃)
• 1,3,5-triazido-2,4,6-tricyanobenzene^[14] – C₉N₁₂ or C₆(CN)₃(N₃)₃

• cyanide – ⁻C≡N ion, cyanide −C≡N and isocyanide −⁺N≡C⁻ functional groups
• dicyanamide (dca⁻) – N(CN)−2 or ⁻N(−C≡N)₂. It forms coordination polymers with metal ions, where it acts as a bridging ligand.^[15]
• tricyanomethanide (tcm⁻) – C(CN)−3 or ⁻C(−C≡N)₃. It acts as a bridging ligand in coordination polymers.^[15] Its conjugate acid is cyanoform.
• pentacyanoethanide – C₂(CN)−5 or (N≡C−)₂C⁻−C(−C≡N)₃
• pentacyanopropenide (pentacyanoallyl anion) – C₃(CN)−5 or (N≡C)−C(C(CN)₂)−2
• pentacyanocyclopentadienide – C₁₀N−5 or C₅(CN)−5
• 2-dicyanomethylene-1,1,3,3-tetracyanopropanediide (tcpd²⁻) – C₁₀N2−6 or C(C(CN)₂)2−3. The anion is approximately D₃ symmetric; each C(CN)₂ group is coplanar with the central carbon atom but tilted with respect to the other groups, in order to relieve steric repulsion between adjacent groups. It acts as a tetradentate bridging ligand in the three-dimensional coordination polymer Cu(tn)(tcpd).^[16]
• azidotetrazolate – CN−7 or N₃−CN₄⁻. It forms salts that are extremely sensitive primary explosives.^[17]
• 5-cyanotetrazolate (ctz⁻) – C₂N−5 or N≡C−CN−4. It acts as a bridging ligand in coordination polymers.^[18]
• tricyanomelaminate – C₆N3−9 or C₃N₃(NCN)3−3
• melonate – C₉N3−13 or C₆N₇(NCN)3−3
• cyanofullerene anions – C₆₀(CN)^–
  _n (n odd) and C₆₀(CN)^2–
  _n (n even). C₆₀(CN)−5 is particularly stable.^[19]: 338 The radical anion C₆₀(CN)^•–
  ₂ has also been prepared, though it is prone to dimerization to [C₆₀(CN)₂]2−2.^[19]: 352
• cyanoacetylide – C₃N⁻ or ⁻C≡C−C≡N. Its conjugate acid is cyanoacetylene.
• cyanopolyynide anions – C_2n+3N⁻ or ⁻C≡C−(C≡C−)_nC≡N (n ≥ 1). Their conjugate acids are the cyanopolyynes.

• Oxocarbon