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Double bond rule
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<h2 id="triple-bonds">Triple bonds</h2> Triple bonds for carbon and nearest neighbours<table><tbody><tr><th></th><th>B<a href="/facts/Boron/Pmwgd7Mf">boron</a>(<i>n</i>=2)</th><th>C<a href="/facts/Carbon/ukrgQexo">carbon</a>(<i>n</i>=2)</th><th>N<a href="/facts/Nitrogen/Nf1QpGDz">nitrogen</a>(<i>n</i>=2)</th><th>O<a href="/facts/Oxygen/acyn6o8r">oxygen</a>(<i>n</i>=2)</th><th>Si<a href="/facts/Silicon/cgWx0hdr">silicon</a>(<i>n</i>=3)</th><th>P<a href="/facts/Phosphorus/27xCeIqs">phosphorus</a>(<i>n</i>=3)</th><th>S<a href="/facts/Sulfur/IK0amTfM">sulfur</a>(<i>n</i>=3)</th><th>Ge<a href="/facts/Germanium/wtoALHGs">germanium</a>(<i>n</i>=4)</th><th>As<a href="/facts/Arsenic/k1c4f44D">arsenic</a>(<i>n</i>=4)</th></tr><tr><th>B</th><td><a href="/facts/Diboryne/EtkulPtk">diborynes</a></td><td>Borataalkynes have been observed<a class="footnote-ref" id="fnref:13" href="#fn:13"><sup>13</sup></a></td><td>Observed in (<a href="/facts/Tert-Butyl/fbTF0UkI"><i>t</i>-Bu</a>)BN(<i>t</i>-Bu) (an <a href="/facts/Iminoborane/GyKrdzgu">iminoborane</a>)</td><td colspan="6"></td></tr><tr><th>C</th><td></td><td><a href="/facts/Alkyne/VHI4N5Wo">alkynes</a></td><td><a href="/facts/Cyanide/t0o8FMKI">cyanides</a></td><td><a href="/facts/Carbon_monoxide/CKuLtEMJ">Carbon monoxide</a> (C≡O)</td><td><a href="/facts/Organosilicon/JvUwzDQ4">silynes</a></td><td><a href="/facts/Phosphaalkyne/j5a6bI11">phosphaalkynes</a></td><td><a href="/facts/Carbon_monosulfide/NmkhFybM">Carbon monosulfide</a> (C≡S)</td><td></td><td><a href="/facts/Arsaalkyne/QlWGGIdI">arsaalkynes</a></td></tr><tr><th>N</th><td colspan="2"></td><td><a href="/facts/Dinitrogen/Nf1QpGDz">Dinitrogen</a>, <a href="/facts/Diazonium/5pkN4G5s">Diazonium</a></td><td colspan="2"></td><td><a href="/facts/Phosphorus_mononitride/cYIpq4Lo">Phosphorus mononitride</a> (P≡N)</td><td colspan="2"></td><td>Arsa-<a href="/facts/Diazonium/5pkN4G5s">diazonium</a><a class="footnote-ref" id="fnref:14" href="#fn:14"><sup>14</sup></a></td></tr><tr><th>O</th><td colspan="4"></td><td><a href="/facts/Silicon_monoxide/Nxr2Q9om">Silicon monoxide</a> has some triple-bond character</td><td colspan="4"></td></tr><tr><th>Si</th><td colspan="4"></td><td><a href="/facts/Disilyne/sXkfm1Yg">disilynes</a></td><td colspan="4"></td></tr><tr><th>P</th><td colspan="5"></td><td><a href="/facts/Diphosphorus/crRKYqB9">Diphosphorus</a></td><td colspan="3"></td></tr><tr><th>S</th><td colspan="6"></td><td>Observed in (I2)2S2+2<a class="footnote-ref" id="fnref:15" href="#fn:15"><sup>15</sup></a></td><td colspan="2"></td></tr><tr><th>Ge</th><td colspan="7"></td><td><a href="/facts/Digermyne/WYKb55Me">Digermyne</a></td><td></td></tr><tr><th>As</th><td colspan="5"></td><td><a href="/facts/Arsenic_monophosphide/Pt8mymIV">Arsenic monophosphide</a> (As≡P)</td><td colspan="3"></td></tr></tbody></table> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Jutzi, Peter (1975). "New Element-Carbon (p-p)π Bonds". Angewandte Chemie International Edition in English. 14 (4): 232–245. doi:10.1002/anie.197502321. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Kutzelnigg, Werner (1984). "Chemical Bonding in Higher Main Group Elements". Angewandte Chemie International Edition. 23 (4): 272–295. doi:10.1002/anie.198402721. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>West, Robert (2002). "Multiple bonds to silicon: 20 years later". Polyhedron. 21 (5–6): 467–472. doi:10.1016/S0277-5387(01)01017-8. <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>Power, Philip P. (2020-12-14). "An Update on Multiple Bonding between Heavier Main Group Elements: The Importance of Pauli Repulsion, Charge-Shift Character, and London Dispersion Force Effects". Organometallics. 39 (23): 4127–4138. doi:10.1021/acs.organomet.0c00200. ISSN 0276-7333. <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>Some research has been done on isomerization of B=NH2 to triple-bonded iminoborane HBNH Rosas-Garcia, Victor M.; Crawford, T. Daniel (2003). "The aminoboranylidene–iminoborane isomerization". The Journal of Chemical Physics. 119 (20): 10647–10652. Bibcode:2003JChPh.11910647R. doi:10.1063/1.1620498. <a href="/wiki/Isomerization" target="_blank">/wiki/Isomerization</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Vidovic, Dragoslav; Moore, Jennifer A.; Jones, Jamie N.; Cowley, Alan H. (2005). "Synthesis and Characterization of a Coordinated Oxoborane: Lewis Acid Stabilization of a Boron−Oxygen Double Bond". Journal of the American Chemical Society. 127 (13): 4566–4567. Bibcode:2005JAChS.127.4566V. doi:10.1021/ja0507564. PMID 15796509. <a href="/wiki/Bibcode_(identifier)" target="_blank">/wiki/Bibcode_(identifier)</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>Franz, Daniel; Szilvási, Tibor; Pöthig, Alexander; Inoue, Shigeyoshi (2019). "Isolation of an N-Heterocyclic Carbene Complex of a Borasilene". Chemistry – A European Journal. 25 (47): 11036–11041. doi:10.1002/chem.201902877. PMID 31241215. S2CID 195660396. <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>Example: Ar*P=B(TMP)2, where Ar* is 2,6-dimesityl-phenyl and TMP is 2,2,6,6-tetramethylpiperidine; see Rivard, Eric; Merrill, W. Alexander; Fettinger, James C.; Wolf, Robert; Spikes, Geoffrey H.; Power, Philip P. (2007). "Boron−Pnictogen Multiple Bonds: Donor-Stabilized PB and AsB Bonds and a Hindered Iminoborane with a B−N Triple Bond". Inorganic Chemistry. 46 (8): 2971–2978. doi:10.1021/ic062076n. PMID 17338516. <a href="/wiki/Mesityl" target="_blank">/wiki/Mesityl</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li> <li id="fn:9"><p>Tokitoh, Norihiro; Ito, Mitsuhiro; Okazaki, Renji (1996). "Formation and reactions of a thioxoborane, a novel boron–sulfur double-bond compound". Tetrahedron Letters. 37 (29): 5145–5148. doi:10.1016/0040-4039(96)01039-8. <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>Zigler, Steven S.; West, Robert; Michl, Josef (1986). "Observation of a Silanimine in an Inert Matrix and in Solution at Low Temperature". Chemistry Letters. 15 (6): 1025–1028. doi:10.1246/cl.1986.1025. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:10" class="footnote-back-ref">↩</a></p></li> <li id="fn:11"><p>Example: Ar*tBuSi=PAr*, where Ar* is 2,4,6-trisiopropylphenyl and tBu is tert-butyl; see Driess, M.; Rell, S.; Merz, K. (1999). "Ungewöhnliche Reaktivität der Silicium-Phosphor-Doppelbindung in einem Silyliden(fluorsilyl)phosphan: Intramolekulare C,H-Inserierung und seine Umwandlung in ein neues Silyliden(silyl)phosphan". Zeitschrift für Anorganische und Allgemeine Chemie. 625 (7): 1119–1123. doi:10.1002/(SICI)1521-3749(199907)625:7<1119::AID-ZAAC1119>3.0.CO;2-1. <a href="/wiki/Tert-butyl" target="_blank">/wiki/Tert-butyl</a> <a href="#fnref:11" class="footnote-back-ref">↩</a></p></li> <li id="fn:12"><p>Suzuki, Hiroyuki; Tokitoh, Norihiro; Nagase, Shigeru; Okazaki, Renji (1994). "The First Genuine Silicon-Sulfur Double-Bond Compound: Synthesis and Crystal Structure of a Kinetically Stabilized Silanethione". Journal of the American Chemical Society. 116 (25): 11578–11579. Bibcode:1994JAChS.11611578S. doi:10.1021/ja00104a052. <a href="/wiki/Bibcode_(identifier)" target="_blank">/wiki/Bibcode_(identifier)</a> <a href="#fnref:12" class="footnote-back-ref">↩</a></p></li> <li id="fn:13"><p>Allwohn, Jürgen; Pilz, Monika; Hunold, Ralf; Massa, Werner; Berndt, Armin (1990). "Compounds with a Boron–Carbon Triple Bond". Angew. Chem. Int. Ed. Engl. 29 (9): 1032–1033. doi:10.1002/anie.199010321. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:13" class="footnote-back-ref">↩</a></p></li> <li id="fn:14"><p>Kuprat, Marcus; Schulz, Axel (2013). "Arsa-Diazonium Salts With an Arsenic–Nitrogen Triple Bond". Angew. Chem. Int. Ed. Engl. 52 (28): 7126–7130. doi:10.1002/anie.201302725. PMID 23740867. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:14" class="footnote-back-ref">↩</a></p></li> <li id="fn:15"><p>Ritter, Stephen K. (March 21, 2005). "Sulfur's Turn for Multiple Bonds". Chemical & Engineering News. <a href="https://cen.acs.org/articles/83/i12/SULFURS-TURN-MULTIPLE-BONDS.html" target="_blank">https://cen.acs.org/articles/83/i12/SULFURS-TURN-MULTIPLE-BONDS.html</a> <a href="#fnref:15" class="footnote-back-ref">↩</a></p></li> </ol>