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Carbon nitride
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<h2 id="covalent-network-compounds">Covalent network compounds</h2> <p>These materials are <a href="/facts/Organic_semiconductor/WjP1RhKW">organic semiconductors</a>. Due to its hydrogen-bonding motifs and <a href="/facts/Electron-rich/GDzV1DXL">electron-rich</a> properties, this carbon material is considered a potential candidate for material applications in carbon supplementation.<a class="footnote-ref" id="fnref:1" href="#fn:1"><sup>1</sup></a> </p> <ul><li><a href="/facts/Beta_carbon_nitride/QSKqhyNC">Beta carbon nitride</a> - a solid with a formula β-C3N4, which is predicted to be harder than diamond.</li> <li><a href="/facts/Graphitic_carbon_nitride/f0xyLRsg">Graphitic carbon nitride</a> - g-C3N4, with important catalytic and sensor properties.<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a></li></ul> <ul><li>Dicyanodiazomethane (N≡C)2C=N+=N−, the only C3N4 isomer studied experimentally</li> <li>Tricyanamide N(C≡N)3 - C3N4 monomer (has never been prepared yet)</li> <li>Dicyanocarbodiimide N≡C−N=C=N−C≡N - another C3N4 monomer (was detected in products of photolysis of <a href="/facts/Cyanuric_triazide/j6W2dJym">triazido-s-triazine</a>).<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a></li></ul> <ul><li>C3N5 - a combined triazole and triazine framework.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a></li> <li>MCN-12 (C3N6) and MCN-13 (C3N7).<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a></li></ul> <h2 id="azafullerenes">Azafullerenes</h2> <ul><li><a href="/facts/Azafullerene/p0eo7P21">Azafullerenes</a> are a class of <a href="/facts/Heterofullerene/phzY87BG">heterofullerenes</a> in which the element substituting for carbon is nitrogen.<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a> Examples include (C59N)2 (biazafullerenyl),<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a> C58N2 (diaza[60]fullerene), C57N3 (triaza[60]fullerene) and C48N12.</li></ul> <h2 id="cyanofullerenes">Cyanofullerenes</h2> <ul><li>Cyanofullerenes are a class of modified <a href="/facts/Fullerene/LPdnl8ox">fullerenes</a> in which cyano- groups are attached to a fullerene skeleton. These have the formula C60(CN)2<i>n</i>, where <i>n</i> takes the values 1 to 9.</li></ul> <h2 id="cyanogen">Cyanogen</h2> <ul><li><a href="/facts/Cyanogen/nsKahJy2">Cyanogen</a> - C2N2 (N≡C−C≡N)</li> <li>Isocyanogen - C2N2 (−C≡N+−C≡N)</li> <li>Diisocyanogen - C2N2 (−C≡N+−+N≡C−)</li> <li><a href="/facts/Cyanogen/nsKahJy2">Paracyanogen</a> - a cyanogen polymer, (NCCN)<i>n</i></li> <li>Paraisocyanogen - a cyanogen polymer, (CNCN)<i>n</i></li></ul> <h2 id="percyanoalkynes--alkenes-and--alkanes">Percyanoalkynes, -alkenes and -alkanes</h2> <ul><li><a href="/facts/Dicyanoacetylene/m0lRY5bE">dicyanoacetylene</a> - C4N2 or N≡C−C≡C−C≡N, also called carbon subnitride or but-2-ynedinitrile</li> <li><a href="/facts/Tetracyanoethylene/NIepxg4e">tetracyanoethylene</a> - C6N4 or (N≡C−)2C=C(−C≡N)2</li> <li><a href="/facts/Tetracyanomethane/QjJ7yHUH">tetracyanomethane</a> - C5N4 or C(−C≡N)4</li> <li>2,2-diisocyanopropanedinitrile - C5N4 or (−C≡N+−)2C(−C≡N)2 also called dicyano(diisocyano)methane</li> <li>hexacyanoethane - C8N6 or (N≡C−)3C−C(−C≡N)3</li> <li>hexacyanocyclopropane - C9N6 or <i>cyclo</i>-C3(CN)6</li> <li>hexacyanobutadiene<a class="footnote-ref" id="fnref:8" href="#fn:8"><sup>8</sup></a> - C10N6 or (N≡C−)2C=C(−C≡N)−C(−C≡N)=C(−C≡N)2</li></ul> <h3>Dicyanopolyynes</h3> <p>Dicyanopolyynes are compounds with the <a href="/facts/Chemical_formula/hghUtthl">chemical formula</a> N≡C(−C≡C−)<i>n</i>C≡N. They are composed of a chain of <a href="/facts/Carbon/ukrgQexo">carbon</a> atoms with alternating <a href="/facts/Single_bond/8qz02fEl">single</a> and <a href="/facts/Triple_bond/poDWRayX">triple bonds</a>, terminated by <a href="/facts/Nitrogen/Nf1QpGDz">nitrogen</a> atoms. Although not <a href="/facts/Polyyne/ReohbKe8">polyynes</a>, <a href="/facts/Cyanogen/nsKahJy2">cyanogen</a> N≡C−C≡N (<i>n</i> = 0) and <a href="/facts/Dicyanoacetylene/m0lRY5bE">dicyanoacetylene</a> N≡C−C≡C−C≡N (<i>n</i> = 1) fit within this series. </p> <ul><li>C6N2 or N≡C(−C≡C−)2C≡N, dicyanobutadiyne or dicyanodiacetylene</li> <li>C8N2 or N≡C(−C≡C−)3C≡N, dicyanohexatriyne or dicyanotriacetylene</li> <li>C10N2 or N≡C(−C≡C−)4C≡N, dicyanooxatetrayne or dicyanotetraacetylene</li> <li>C12N2 or N≡C(−C≡C−)5C≡N, dicyanodecapentayne or dicyanopentaacetylene</li> <li>C14N2 or N≡C(−C≡C−)6C≡N, dicyanododecahexayne or dicyanohexaacetylene</li> <li>C16N2 or N≡C(−C≡C−)7C≡N, dicyanotetradecaheptayne or dicyanoheptaacetylene</li> <li>C18N2 or N≡C(−C≡C−)8C≡N, dicyanohexadecaoctayne or dicyanooctaacetylene</li> <li>C20N2 or N≡C(−C≡C−)9C≡N, dicyanooctadecanonayne or dicyanononaacetylene</li> <li>C22N2 or N≡C(−C≡C−)10C≡N, dicyanoicosadecayne or dicyanodecaacetylene</li></ul> <h2 id="perazidoalkynes--alkenes-and--alkanes">Perazidoalkynes, -alkenes and -alkanes</h2> <ul><li><a href="/facts/Tetraazidomethane/6zA7Clvp">tetraazidomethane</a> - CN12 or C(−N=N+=N−)4</li></ul> <h2 id="percyanoheterocycles">Percyanoheterocycles</h2> <ul><li>pentacyano<a href="/facts/Pyridine/X817hCch">pyridine</a> - C10N6</li> <li>tetracyano<a href="/facts/Pyrazine/fxCa3uuI">pyrazine</a> - C8N6</li> <li>tricyano<a href="/facts/Triazine/IxQSQjk9">triazine</a> - C6N6<a class="footnote-ref" id="fnref:9" href="#fn:9"><sup>9</sup></a></li> <li>tetracyano-bitriazine - C10N10<a class="footnote-ref" id="fnref:10" href="#fn:10"><sup>10</sup></a></li> <li>dicyano<a href="/facts/Tetrazine/FxgrNJk3">tetrazine</a> - C4N6</li> <li>hexacyanotris<a href="/facts/Imidazole/5MybM6Hh">imidazole</a> - C15N12</li> <li>hexacyanohexaaza<a href="/facts/Triphenylene/nXUhGdpp">triphenylene</a> - C18N12</li></ul> <h2 id="aromatic-cyanocarbons">Aromatic cyanocarbons</h2> <ul><li>hexacyano<a href="/facts/Benzene/Fguue7nr">benzene</a> - C12N6 or C6(CN)6</li> <li>octacyano<a href="/facts/Naphthalene/RU2sV8mN">naphthalene</a> - C18N8 or C10(CN)8</li> <li>decacyano<a href="/facts/Anthracene/mV8Sblcq">anthracene</a> - C24N10 or C14(CN)10</li></ul> <h2 id="other-compounds">Other compounds</h2> <ul><li>cyano<a href="/facts/Nitrene/2J1DGmJD">nitrene</a> - CN2 or [N≡C−N ⇌ −N=C=N+ ⇌ +N=C=N− ⇌ N−C≡N] (one of the nitrogens is <a href="/facts/Valence_(chemistry)/ck7cHByj">univalent</a>)</li> <li>azodicarbonitrile - C2N4 or N≡C−N=N−C≡N, <a href="/facts/Cis%25E2%2580%2593trans_isomerism/vqlchJly"><i>cis</i></a> and <a href="/facts/Cis%25E2%2580%2593trans_isomerism/vqlchJly"><i>trans</i></a> <a href="/facts/Isomers/PXlvDVdg">isomers</a></li> <li><a href="/facts/Cyanogen_azide/bRJLPtbR">cyanogen azide</a> - CN4 or N≡C−N=N+=N−</li> <li><a href="/facts/1-diazidocarbamoyl-5-azidotetrazole/qLD3c5G9">1-diazidocarbamoyl-5-azidotetrazole</a> - C2N14</li> <li>2,2′-azobis(5-azidotetrazole) - C2N16</li> <li><a href="/facts/Triazidotriazine/j6W2dJym">triazidotriazine</a> (cyanuric triazide) - C3N12 (C3N3(N3)3)</li> <li>triazidoheptazine - C6N16 (C6N7(N3)3)</li> <li>tricyanomethanimine (dicyanomethylene-cyanamide) - C4N4 or N≡C−N=C(−C≡N)2</li> <li>diazidodicyanoethylene - C4N8 or (−N=N+=N−)2C=C(−C≡N)2 and (−N=N+=N−)(N≡C−)C=C(−N=N+=N−)(−C≡N), <i>cis</i> and <i>trans</i></li> <li>dicyanodiazomethane - C3N4 or (N≡C−)2C=N+=N−</li> <li>dicyanocarbene - C3N2 or CII(−C≡N)2 (and isomers cyanoisocyanocarbene −C≡N+−CII−C≡N, diisocyanocarbene −C≡N+−CII−+N≡C−, 3-cyano-2<i>H</i>-azirenylidene and 3-isocyano-2<i>H</i>-azirenylidene)</li> <li>1,3,5-triazido-2,4,6-tricyanobenzene - C9N12 (C6(CN)3(N3)3)</li> <li>nitrogen tricyanide N(−C≡N)3 and carbon bis(cyanamide) N≡C−N=C=N−C≡N, two formal monomers of polymeric C3N4</li></ul> <h2 id="anions-and-functional-groups">Anions and functional groups</h2> <ul><li><a href="/facts/Cyanide/t0o8FMKI">cyanide</a> - −C≡N ion, <a href="/facts/Nitrile/Gz7RCnC6">cyanide</a> −C≡N and <a href="/facts/Isocyanide/VmkIBMKR">isocyanide</a> −+N≡C− functional groups</li> <li><a href="/facts/Dicyanamide/laMq7kMK">dicyanamide</a> - N(CN)−2 or −N(−C≡N)2</li> <li>tricyanomethanide - C(CN)−3 or −C(−C≡N)3</li> <li>pentacyanoethanide - C2(CN)−5 or (N≡C−)2C−−C(−C≡N)3</li> <li>pentacyanopropenide (pentacyanoallyl anion) - C3(CN)−5</li> <li>2-dicyanomethylene-1,1,3,3-tetracyanopropanediide C10N2−6</li> <li>tricyanomelaminate anion - C3N3(NCN)3−3</li> <li>melonate - C6N7(NCN)3−3</li> <li>cyanofullerene anions - C60(CN)<i>n</i>− (<i>n</i> odd) and C60(CN)<i>n</i>2− (<i>n</i> even)</li> <li>cyanoacetlyide - C3N− or −C≡C−C≡N</li> <li>cyanobutadiynylide - C5N− or −C≡C−C≡C−C≡N</li> <li>cyanopolyynide anions - C<i>n</i>N− (<i>n</i> odd)</li></ul> <h2 id="see-also">See also</h2> <ul><li><a href="/facts/Oxocarbon/LtfIXVv5">Oxocarbon</a></li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>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. <a href="978-0-12-823961-2" target="_blank">978-0-12-823961-2</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>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. <a href="https://doi.org/10.1016%2Fj.snb.2017.10.053" target="_blank">https://doi.org/10.1016%2Fj.snb.2017.10.053</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>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 <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>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 <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>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 <a href="https://onlinelibrary.wiley.com/doi/am-pdf/10.1002/smll.201903572" target="_blank">https://onlinelibrary.wiley.com/doi/am-pdf/10.1002/smll.201903572</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>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 <a href="http://www.usc.edu/CSSF/History/1993/S05.html" target="_blank">http://www.usc.edu/CSSF/History/1993/S05.html</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>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 <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> <li id="fn:8"><p>O.W.Webster, Hexacyanobutadiene, J. Am. Chem. Soc. 86(14): 2898–2902 (1964) <a href="http://pubs.acs.org/doi/abs/10.1021/ja01068a026?journalCode=jacsat" target="_blank">http://pubs.acs.org/doi/abs/10.1021/ja01068a026?journalCode=jacsat</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li> <li id="fn:9"><p>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 <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:9" class="footnote-back-ref">↩</a></p></li> <li id="fn:10"><p>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 <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:10" class="footnote-back-ref">↩</a></p></li> </ol>