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Arenium ion
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<h2 id="see-also">See also</h2> <ul><li><a href="/facts/Aryl_radical/5HU17jch">Aryl radical</a></li> <li><a href="/facts/Cyclopentadienyl_anion/11slGTQo">Cyclopentadienyl anion</a></li> <li><a href="/facts/Meisenheimer_complex/xVjBKcuv">Meisenheimer complex</a>, the analogous intermediate in nucleophilic aromatic substitution</li> <li><a href="/facts/Tropylium_cation/3vAk8fwQ">Tropylium cation</a></li></ul> <h2 id="some-historic-references">Some historic references</h2> <ul><li><a href="/facts/George_A._Olah/yn3favWM">Olah, G. A.</a> (1972). "Stable carbocations. CXVIII. General concept and structure of carbocations based on differentiation of trivalent (classical) carbenium ions from three-center bound penta- or tetracoordinated (nonclassical) carbonium ions. Role of carbocations in electrophilic reactions". <i>J. Am. Chem. Soc</i>. 94 (3): 808–820. <a href="/facts/Doi_(identifier)/muM9Etpq">doi</a>:<a href="https://doi.org/10.1021%2Fja00758a020">10.1021/ja00758a020</a>.</li> <li>Wheland, G. W. (1942). "A Quantum Mechanical Investigation of the Orientation of Substituents in Aromatic Molecules". <i>J. Am. Chem. Soc</i>. 64 (4): 900–908. <a href="/facts/Doi_(identifier)/muM9Etpq">doi</a>:<a href="https://doi.org/10.1021%2Fja01256a047">10.1021/ja01256a047</a>.</li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, p. 658, ISBN 978-0-471-72091-1 <a href="978-0-471-72091-1" target="_blank">978-0-471-72091-1</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Smith, Michael B. (18 October 2010). Organic Chemistry: An Acid—Base Approach. CRC Press. ISBN 9781439894620 – via Google Books. <a href="9781439894620" target="_blank">9781439894620</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>More commonly, sigma complex usually refers to a type of organometallic complex. <a href="/wiki/Sigma_complex" target="_blank">/wiki/Sigma_complex</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Sykes, Peter. A Guidebook to Mechanism in Organic Chemistry. pp. 130–133.[ISBN missing] <a href="/wiki/Peter_Sykes_(chemist)" target="_blank">/wiki/Peter_Sykes_(chemist)</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Reed, C. A.; Kim, K.; Stoyanov, E. S.; Stasko, D.; Tham, F. S.; Mueller, L. J.; Boyd, P. D. W. (2003). "Isolating Benzenium Ion Salts". J. Am. Chem. Soc. 125 (7): 1796–804. doi:10.1021/ja027336o. PMID 12580605. S2CID 8938028. <a href="http://www.escholarship.org/uc/item/5c0780qn" target="_blank">http://www.escholarship.org/uc/item/5c0780qn</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Poverenov, E.; Leitus, G.; Milstein, D. (2006). "Synthesis and Reactivity of the Methylene Arenium Form of a Benzyl Cation, Stabilized by Complexation". J. Am. Chem. Soc. (Communication). 128 (51): 16450–1. doi:10.1021/ja067298z. PMID 17177364. <a href="https://figshare.com/articles/journal_contribution/3038599" target="_blank">https://figshare.com/articles/journal_contribution/3038599</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> </ol>