Carbon nitride

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-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 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

Dicyanopolyynes

See also: Cyanopolyyne

Dicyanopolyynes are compounds with the chemical formula N≡C(−C≡C−)nC≡N (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≡C−C≡N (n = 0) and dicyanoacetylene N≡C−C≡C−C≡N (n = 1) also fit within this series.

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 or C6(CN)6
  • octacyanonaphthalene - C18N8 or C10(CN)8
  • decacyanoanthracene - C24N10 or C14(CN)10

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, cis and trans isomers
  • cyanogen azide - CN4 or N≡C−N=N+=N−
  • 1-diazidocarbamoyl-5-azidotetrazole - C2N14
  • 2,2′-azobis(5-azidotetrazole) - C2N16
  • dicyanocarbene[9] - 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)
  • 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 (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

Anions and functional groups

  • 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 - C2n+3N− or −C≡C−(C≡C−)nC≡N (n ≥ 1). Their conjugate acids are the cyanopolyynes.

See also

References

  1. ^ 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.
  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.
  3. ^ 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
  4. ^ 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
  5. ^ 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
  6. ^ 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
  7. ^ O.W.Webster, Hexacyanobutadiene, J. Am. Chem. Soc. 86(14): 2898–2902 (1964)
  8. ^ 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
  9. ^ Ciganek, Engelbert (May 1966). "Dicyanocarbene". Journal of the American Chemical Society. 88 (9): 1979–1988. doi:10.1021/ja00961a023.
  10. ^ Ciganek, Engelbert (December 1965). "Dicyanodiazomethane". The Journal of Organic Chemistry. 30 (12): 4198–4204. doi:10.1021/jo01023a050.
  11. ^ 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
  12. ^ a b Hall, H. K. Jr.; Ramezanian, M.; Saeva, F. D. (January 1988). "A new azacyanocarbon, C4N4: tricyanomethanimine". Tetrahedron Letters. 29 (11): 1235–1238. doi:10.1016/S0040-4039(00)80264-6.
  13. ^ Miller, Dale R.; Swenson, Dale C.; Gillan, Edward G. (1 May 2004). "Synthesis and Structure of 2,5,8-Triazido-s-Heptazine: An Energetic and Luminescent Precursor to Nitrogen-Rich Carbon Nitrides". Journal of the American Chemical Society. 126 (17): 5372–5373. doi:10.1021/ja048939y.
  14. ^ Becker, Martin; Voss, Karsten; Villinger, Alexander; Schulz, Axel (1 June 2012). "An Efficient Route to 1,3,5-Triazido-2,4,6-tricyanobenzene". Zeitschrift für Naturforschung B. 67 (6): 643–649. doi:10.5560/znb.2012-0092.
  15. ^ a b Batten, Stuart R; Murray, Keith S (November 2003). "Structure and magnetism of coordination polymers containing dicyanamide and tricyanomethanide". Coordination Chemistry Reviews. 246 (1–2): 103–130. doi:10.1016/S0010-8545(03)00119-X.
  16. ^ Thétiot, F.; Triki, S.; Pala, J. Sala; Gómez-García, C.J. (September 2005). "Polynitrile anions as ligands: synthesis, structure and magnetic properties of a new three-dimensional coordination polymer with the 2-dicyanomethylene-1,1,3,3-tetracyanopropanediide (tcpd2−) bridging ligand". Synthetic Metals. 153 (1–3): 481–484. doi:10.1016/j.synthmet.2005.07.297.
  17. ^ Klapötke, Thomas M.; Stierstorfer, Jörg (28 January 2009). "The CN7− Anion". Journal of the American Chemical Society. 131 (3): 1122–1134. doi:10.1021/ja8077522.
  18. ^ Szafranowska, Barbara; Beck, Johannes (12 June 2013). "5‐Cyanotetrazolate as a Ligand and Linker in Copper(II) Complexes and Coordination Polymers". European Journal of Inorganic Chemistry. 2013 (18): 3167–3177. doi:10.1002/ejic.201201483.
  19. ^ a b Konarev, Dmitry V; Lyubovskaya, Rimma N (30 April 2012). "Molecular design, study of the structures and properties of ionic fullerene compounds". Russian Chemical Reviews. 81 (4): 336–366. doi:10.1070/RC2012v081n04ABEH004273.
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