Carbon nitride
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Chemical compound made of only carbon and nitrogen
Carbon nitrides are organic compounds consisting only of carbon and nitrogen atoms.
Covalent network compounds
[edit ]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]
Azafullerenes
[edit ]- 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
[edit ]- 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
[edit ]- 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
[edit ]- 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
[edit ]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
[edit ]- tetraazidomethane - CN12 or C(−N=N+=N−)4
Percyanoheterocycles
[edit ]- pentacyanopyridine - C10N6
- tetracyanopyrazine - C8N6
- tricyanotriazine - C6N6[9]
- tetracyano-bitriazine - C10N10[9]
- dicyanotetrazine - C4N6
- hexacyanotrisimidazole - C15N12
- hexacyanohexaazatriphenylene - C18N12
Aromatic cyanocarbons
[edit ]- hexacyanobenzene - C12N6 or C6(CN)6
- octacyanonaphthalene - C18N8 or C10(CN)8
- decacyanoanthracene - C24N10 or C14(CN)10
Other compounds
[edit ]- 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 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
[edit ]- 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
[edit ]References
[edit ]- ^ 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.
- ^ 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年10月05日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
- ^ 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
- ^ 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
- ^ 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年03月04日 at the Wayback Machine
- ^ 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
- ^ O.W.Webster, Hexacyanobutadiene, J. Am. Chem. Soc. 86(14): 2898–2902 (1964)
- ^ a b 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