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. Beta carbon nitride – a solid with a formula , which is predicted to be harder than diamond. Graphitic carbon nitride – , with important catalytic and sensor properties. – a combined triazole and triazine framework.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. MCN-12 () and MCN-13 ().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.
Azafullerenes
Azafullerenes are a class of heterofullerenes in which the element substituting for carbon is nitrogen.D.J. Harris, Discovery of Nitroballs: Research in Fullerene Chemistry, 1993 California State Science Fair, http://www.usc.edu/CSSF/History/1993/S05.html Examples include (biazafullerenyl),Hummelen et al, "Isolation of the Heterofullerene C59N as Its Dimer (C59N)2", Science 269: 1554-1556 (1995). (diazafullerene), (triazafullerene) 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- hexacyanobutadieneO.W.Webster, Hexacyanobutadiene, J. Am. Chem. Soc. 86(14): 2898–2902 (1964) – or
Dicyanopolyynes
Dicyanopolyynes are compounds with the chemical formula (n = 2–10). They are composed of a chain of carbon atoms with alternating single and triple bonds, terminated by nitrogen atoms. Although not polyynes, cyanogen (n = 0) and dicyanoacetylene (n = 1) also fit within this series.
Perazidoalkynes, -alkenes and -alkanes
tetraazidomethane – or
Percyanoheterocycles
pentacyanopyridine – tetracyanopyrazine – tricyanotriazine – 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). tetracyano-bitriazine – dicyanotetrazine – hexacyanotrisimidazole – hexacyanohexaazatriphenylene –
Aromatic cyanocarbons
hexacyanobenzene – or octacyanonaphthalene – or decacyanoanthracene – or
Other compounds
cyanonitrene – or (one of the nitrogens is univalent) – or , cis and trans isomers cyanogen azide – or 1-diazidocarbamoyl-5-azidotetrazole – – – or (and isomers cyanoisocyanocarbene , diisocyanocarbene , 3-cyano-2H-azirenylidene and 3-isocyano-2H-azirenylidene) dicyanodiazomethane – or , the only isomer prepared in bulk tricyanamide (nitrogen tricyanide) – or , has never been prepared yet dicyanocarbodiimide (carbon bis(cyanamide)) – or , detected in photolysis products of triazido-s-triazineSato, 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. cyanuric triazide (triazido-s-triazine) – or (tricyanomethanimine) – or diazidodicyanoethylene – or and , cis and trans 2,5,8-triazido-s-heptazine – () 1,3,5-triazido-2,4,6-tricyanobenzene – or
Anions and functional groups
cyanide – ion, cyanide and isocyanide functional groups dicyanamide (dca−) – or . It forms coordination polymers with metal ions, where it acts as a bridging ligand. tricyanomethanide (tcm−) – or . It acts as a bridging ligand in coordination polymers. Its conjugate acid is cyanoform. pentacyanoethanide – or pentacyanopropenide (pentacyanoallyl anion) – or pentacyanocyclopentadienide – or 2-dicyanomethylene-1,1,3,3-tetracyanopropanediide (tcpd2−) – or . The anion is approximately D3 symmetric; each 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 . azidotetrazolate – or . It forms salts that are extremely sensitive primary explosives. 5-cyanotetrazolate (ctz−) – or . It acts as a bridging ligand in coordination polymers. tricyanomelaminate – or melonate – or anions – (n odd) and (n even). is particularly stable. The radical anion has also been prepared, though it is prone to dimerization to . cyanoacetylide – or . Its conjugate acid is cyanoacetylene. cyanopolyynide anions – or (n ≥ 1). Their conjugate acids are the cyanopolyynes.
See also Oxocarbon
References