Carbon nitride
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]
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
- tetraazidomethane - CN12 or C(−N=N+=N−)4
Percyanoheterocycles
- pentacyanopyridine - C10N6
- tetracyanopyrazine - C8N6
- tricyanotriazine - C6N6[8]
- tetracyano-bitriazine - C10N10[8]
- dicyanotetrazine - C4N6
- hexacyanotrisimidazole - C15N12
- hexacyanohexaazatriphenylene - C18N12
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, 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
- ISBN 978-0-12-823961-2.
- .
- ^ 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
- ^ O.W.Webster, Hexacyanobutadiene, J. Am. Chem. Soc. 86(14): 2898–2902 (1964)
- ^