Chemistry:Carbon nitride
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Short description: Chemical compound made of only carbon and nitrogen
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.[1]
- Beta carbon nitride - a solid with a formula β-C
3N
4, which is predicted to be harder than diamond. - Graphitic carbon nitride - g-C
3N
4, with important catalytic and sensor properties.[2]
- Dicyanodiazomethane (N≡C)
2C=N+
=N−
, the only C
3N
4 isomer studied experimentally - Tricyanamide N(C≡N)
3 - C
3N
4 monomer (has never been prepared yet) - Dicyanocarbodiimide N≡C–N=C=N–C≡N - another C
3N
4 monomer (was detected in products of photolysis of triazido-s-triazine).[3]
Azafullerenes
- Azafullerenes are a class of heterofullerenes in which the element substituting for carbon is nitrogen.[6] Examples include (C
59N)
2 (biazafullerenyl),[7] C
58N
2 (diaza[60]fullerene), C
57N
3 (triaza[60]fullerene) and C
48N
12.
Cyanofullerenes
- Cyanofullerenes are a class of modified fullerenes in which cyano- groups are attached to a fullerene skeleton. These have the formula C
60(CN)
2n, where n takes the values 1 to 9.
Cyanogen
- Cyanogen - C
2N
2 (N≡C–C≡N) - Isocyanogen - C
2N
2 (−
C≡N+
–C≡N) - Diisocyanogen - C
2N
2 (−
C≡N+
–+
N≡C−
) - Paracyanogen - a cyanogen polymer, (NCCN)
n - Paraisocyanogen - a cyanogen polymer, (CNCN)
n
Percyanoalkynes, -alkenes and -alkanes
- dicyanoacetylene - C
4N
2 or N≡C–C≡C–C≡N, also called carbon subnitride or but-2-ynedinitrile - tetracyanoethylene - C
6N
4 or (N≡C–)
2C=C(–C≡N)
2 - tetracyanomethane - C
5N
4 or C(–C≡N)
4 - 2,2-diisocyanopropanedinitrile - C
5N
4 or (−
C≡N+
–)
2C(–C≡N)
2 also called dicyano(diisocyano)methane - hexacyanoethane - C
8N
6 or (N≡C–)
3C–C(–C≡N)
3 - hexacyanocyclopropane - C
9N
6 or cyclo-C
3(CN)
6 - hexacyanobutadiene[8] - C
10N
6 or (N≡C–)
2C=C(–C≡N)–C(–C≡N)=C(–C≡N)
2
Dicyanopolyynes
Dicyanopolyynes are compounds with the chemical formula N≡C(–C≡C–)
nC≡N. They are composed of a chain of carbon atoms with alternating single and triple bonds, terminated by nitrogen atoms. Although not polyynes, cyanogen N≡C–C≡N (n = 0) and dicyanoacetylene N≡C–C≡C–C≡N (n = 1) fit within this series.
- C
6N
2 or N≡C(–C≡C–)
2C≡N, dicyanobutadiyne or dicyanodiacetylene - C
8N
2 or N≡C(–C≡C–)
3C≡N, dicyanohexatriyne or dicyanotriacetylene - C
10N
2 or N≡C(–C≡C–)
4C≡N, dicyanooxatetrayne or dicyanotetraacetylene - C
12N
2 or N≡C(–C≡C–)
5C≡N, dicyanodecapentayne or dicyanopentaacetylene - C
14N
2 or N≡C(–C≡C–)
6C≡N, dicyanododecahexayne or dicyanohexaacetylene - C
16N
2 or N≡C(–C≡C–)
7C≡N, dicyanotetradecaheptayne or dicyanoheptaacetylene - C
18N
2 or N≡C(–C≡C–)
8C≡N, dicyanohexadecaoctayne or dicyanooctaacetylene - C
20N
2 or N≡C(–C≡C–)
9C≡N, dicyanooctadecanonayne or dicyanononaacetylene - C
22N
2 or N≡C(–C≡C–)
10C≡N, dicyanoicosadecayne or dicyanodecaacetylene
Perazidoalkynes, -alkenes and -alkanes
- tetraazidomethane - CN
12 or C(–N=N+
=N−
)
4
Percyanoheterocycles
- pentacyanopyridine - C
10N
6 - tetracyanopyrazine - C
8N
6 - tricyanotriazine - C
6N
6[9] - tetracyano-bitriazine - C
10N
10[9] - dicyanotetrazine - C
4N
6 - hexacyanotrisimidazole - C
15N
12 - hexacyanohexaazatriphenylene - C
18N
12
Aromatic cyanocarbons
- hexacyanobenzene - C
12N
6 or C
6(CN)
6 - octacyanonaphthalene - C
18N
8 or C
10(CN)
8 - decacyanoanthracene - C
24N
10 or C
14(CN)
10
Other compounds
- cyanonitrene - CN
2 or [N≡C–N ⇌ −
N=C=N+
⇌ +
N=C=N−
⇌ N–C≡N] (one of the nitrogens is univalent) - azodicarbonitrile - C
2N
4 or N≡C–N=N–C≡N, cis and trans isomers - cyanogen azide - CN
4 or N≡C–N=N+
=N− - 1-diazidocarbamoyl-5-azidotetrazole - C
2N
14 - 2,2′-azobis(5-azidotetrazole) - C
2N
16 - triazidotriazine (cyanuric triazide) - C
3N
12 (C
3N
3(N
3)
3) - triazidoheptazine - C
6N
16 (C
6N
7(N
3)
3) - tricyanomethanimine (dicyanomethylene-cyanamide) - C
4N
4 or N≡C–N=C(–C≡N)
2 - diazidodicyanoethylene - C
4N
8 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 - C
3N
4 or (N≡C–)
2C=N+
=N− - dicyanocarbene - C
3N
2 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 - C
9N
12 (C
6(CN)
3(N
3)
3) - nitrogen tricyanide N(–C≡N)
3 and carbon bis(cyanamide) N≡C–N=C=N–C≡N, two formal monomers of polymeric C
3N
4
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 - C
2(CN)−
5 or (N≡C–)
2C−
–C(–C≡N)
3 - pentacyanopropenide (pentacyanoallyl anion) - C
3(CN)−
5 - 2-dicyanomethylene-1,1,3,3-tetracyanopropanediide C
10N2−
6 - tricyanomelaminate anion - C
3N
3(NCN)3−
3 - melonate - C
6N
7(NCN)3−
3 - cyanofullerene anions - C
60(CN)
n−
(n odd) and C
60(CN)
n2− (n even) - cyanoacetlyide - C
3N−
or −
C≡C–C≡N - cyanobutadiynylide - C
5N−
or −
C≡C–C≡C–C≡N - cyanopolyynide anions - C
nN−
(n odd)
See also
References
- ↑ 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.2017.10.053.
- ↑ 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
- ↑ 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)
- ↑ 9.0 9.1 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
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