{"id":11757,"date":"2013-12-06T14:26:10","date_gmt":"2013-12-06T14:26:10","guid":{"rendered":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=11757"},"modified":"2014-03-02T06:38:18","modified_gmt":"2014-03-02T06:38:18","slug":"does-forming-a-wheland-intermediate-disrupt-all-aromaticity","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=11757","title":{"rendered":"Does forming a Wheland intermediate disrupt all aromaticity?"},"content":{"rendered":"
\n

Text books will announce that during aromatic electrophilic substitution, aromaticity is lost by the formation of a Wheland intermediate (and regained by eliminating a proton). Is that entirely true?\"wheland\"<\/a><\/p>\n

I will start by considering the simplest of all such intermediates[1]<\/a><\/span>,[2]<\/a><\/span> the NMR of which was first reported by Olah and which is shown below (red). The values in black are from a \u03c9B97XD\/6-311G(d,p) calculation (chloroform)[3]<\/a><\/span>. The discrepancy might be due to the difference in solvent (HF-SbF5<\/sub>\/SO2<\/sub>ClF-SO2F2<\/sub>) and my failure to include a counter-ion in the calculation.\u2021<\/sup>\u00a0Actually, this result is only obtained at -134\u00b0C; warming to -70\u00b0C increases the rate of [1,2] ring shifts<\/a> and only one “aromatic” peak at 8.09 ppm is observed.<\/p>\n

\"Click

Click for 3D to see vibrational modes<\/p><\/div>\n

\u00a0The computed MOs are shown below. MOs 21 and 15 are pretty much identical with those for benzene itself (the former because of symmetry), \u00a0so relatively little disruption of the conjugation there. An NBO analysis shows that each C-H bond from the sp3<\/sup> centre acts as a donor to the\u00a0\u03c0-system (E2 = 8.5 kcal\/mol), which we know in another guise as hyperconjugation or \u03c3-conjugation. In this sense, the two C-H bonds are acting as surrogates for a real p-AO on that carbon, and the E2 value is certainly not insignificant. Certainly they are nowhere near as good a donor as one real p-AO, but nonetheless, the two of them together are good enough to result in retention of a significant measure of cyclic\u00a0\u03c0-conjugation, and hence probably aromaticity. The C-H bonds are weakened as a result of their electron donation, which reduces their normal mode wavenumber down by about 200 cm-1<\/sup>. The so-called Kekule-mode<\/a>, which is depressed in benzene itself to about 1300 cm-1<\/sup> because of the effect termed \u03c0-distortivity[4]<\/a><\/span>, is actually increased to 1442 cm -1<\/sup> in the Wheland intermediate.[5]<\/a><\/span> This mode is normally elevated by any weakening of the distortive \u03c0-system (in my previous post<\/a>, I noted such an elevation induced by the quintet excited state of benzene) and so we many presume the same effect operates in the Wheland intermediate.<\/p>\n\n\n\n\n
\u00a0
\n
\"Click

MO 20 Click for 3D<\/p><\/div>\n<\/td>\n

\u00a0
\n
\"Click

MO 21 Click for 3D<\/p><\/div>\n<\/td>\n<\/tr>\n

\n
\"Click

MO 15 Click for 3D<\/p><\/div>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

To get a measure of any aromaticity deriving from a ring current, I computed the NICS(1) value from the ring centroid. This latter was itself obtained from the coordinates of the ring-critical-point<\/em> determined by a QTAIM analysis, and computed at that point and 1, 2 and 3\u00c5 above it. The NICS values are respectively -0.4, -6.1, -3.6 and -1.6 ppm. The maximum is indeed the NICS(1) point, and at that point, the value indicates modest, but real \u03c0-aromaticity.<\/p>\n

\"wheland-NICS\"<\/p>\n

So does forming a Wheland intermediate disrupt all aromaticity? The answer is a clear no! What might be interesting to compute (I have not tried doing so here) is an actual energy for the stabilisation resulting from the weak aromaticity present as a % of that present in benzene, so that the text-books can be amended.<\/p>\n

\n

\u2021<\/sup> It might also be that the exchange in the measured NMR spectrum was not entirely suppressed, and so some residual averaging of the peak positions remains.<\/p>\n

References<\/h2>\n
  1. G.A. Olah, R.H. Schlosberg, D.P. Kelly, and G.D. Mateescu, \"Stable carbonium ions. IC. Benzenonium ion (C6H7+) and its degenerate rearrangement\", Journal of the American Chemical Society<\/i>, vol. 92, pp. 2546-2548, 1970. https:\/\/doi.org\/10.1021\/ja00711a057<\/a>\n\n<\/li>\n
  2. G.A. Olah, R.H. Schlosberg, R.D. Porter, Y.K. Mo, D.P. Kelly, and G.D. Mateescu, \"Stable carbocations. CXXIV. Benzenium ion and monoalkylbenzenium ions\", Journal of the American Chemical Society<\/i>, vol. 94, pp. 2034-2043, 1972. https:\/\/doi.org\/10.1021\/ja00761a041<\/a>\n\n<\/li>\n
  3. S. Shaik, A. Shurki, D. Danovich, and P.C. Hiberty, \"A Different Story of \u03c0-DelocalizationThe Distortivity of \u03c0-Electrons and Its Chemical Manifestations\", Chemical Reviews<\/i>, vol. 101, pp. 1501-1540, 2001. https:\/\/doi.org\/10.1021\/cr990363l<\/a>\n\n<\/li>\n
  4. H.S. Rzepa, \"Gaussian Job Archive for C6H7(1+)\", 2013. https:\/\/doi.org\/10.6084\/m9.figshare.870473<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> ","protected":false},"excerpt":{"rendered":"

    Text books will announce that during aromatic electrophilic substitution, aromaticity is lost by the formation of a Wheland intermediate (and regained by eliminating a proton). Is that entirely true? I will start by considering the simplest of all such intermediates, the NMR of which was first reported by Olah and which is shown below (red). 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Is that entirely true? I will start by considering the simplest of all such intermediates, the NMR of which was first reported by Olah and which is shown below (red). […]","og_url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=11757","og_site_name":"Henry Rzepa's Blog","article_published_time":"2013-12-06T14:26:10+00:00","article_modified_time":"2014-03-02T06:38:18+00:00","og_image":[{"url":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/12\/wheland.svg","type":"","width":"","height":""}],"author":"Henry Rzepa","twitter_card":"summary_large_image","twitter_misc":{"Written by":"Henry Rzepa","Estimated reading time":"3 minutes"},"schema":{"@context":"https:\/\/schema.org","@graph":[{"@type":"Article","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=11757#article","isPartOf":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=11757"},"author":{"name":"Henry Rzepa","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/#\/schema\/person\/2b40f7b9c872a4dc1547e040a11b6281"},"headline":"Does forming a Wheland intermediate disrupt all aromaticity?","datePublished":"2013-12-06T14:26:10+00:00","dateModified":"2014-03-02T06:38:18+00:00","mainEntityOfPage":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=11757"},"wordCount":575,"commentCount":25,"image":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=11757#primaryimage"},"thumbnailUrl":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/12\/wheland.svg","keywords":["actual energy"],"articleSection":["Interesting chemistry"],"inLanguage":"en-GB","potentialAction":[{"@type":"CommentAction","name":"Comment","target":["https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=11757#respond"]}]},{"@type":"WebPage","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=11757","url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=11757","name":"Does forming a Wheland intermediate disrupt all aromaticity? 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Hence electronic\u00a0arrow pushing as a term. But here I argue that the true origin of this immensely powerful technique in chemistry goes back to the 19th century.\u2026","rel":"","context":"In "Interesting chemistry"","block_context":{"text":"Interesting chemistry","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=4"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2010\/09\/wheland.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":9917,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=9917","url_meta":{"origin":11757,"position":1},"title":"Concerted vs stepwise (Meisenheimer) mechanisms for aromatic nucleophilic substitution.","author":"Henry Rzepa","date":"March 25, 2013","format":false,"excerpt":"My two previous explorations of aromatic substitutions have involved an electrophile (NO+ or Li+). Time now to look at a nucleophile, representing nucleophilic aromatic substitution. The mechanism of this is thought to pass through an intermediate analogous to the Wheland for an electrophile, this time known as the Meisenheimer complex.\u2026","rel":"","context":"In "Interesting chemistry"","block_context":{"text":"Interesting chemistry","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=4"},"img":{"alt_text":"Click for 3D.","src":"https:\/\/i0.wp.com\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/03\/trinitro.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":12056,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=12056","url_meta":{"origin":11757,"position":2},"title":"The mechanism of diazo coupling: more hidden mechanistic intermediates.","author":"Henry Rzepa","date":"March 8, 2014","format":false,"excerpt":"The diazo-coupling reaction dates back to the 1850s (and a close association with Imperial College via the first professor of chemistry there, August von Hofmann) and its mechanism was much studied in the heyday of physical organic chemistry. Nick Greeves, purveyor of the excellent ChemTube3D site, contacted me about the\u2026","rel":"","context":"In "reaction mechanism"","block_context":{"text":"reaction mechanism","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=1086"},"img":{"alt_text":"cis-diazo","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2014\/03\/cis-diazo.gif?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":17805,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=17805","url_meta":{"origin":11757,"position":3},"title":"Silyl cations?","author":"Henry Rzepa","date":"March 23, 2017","format":false,"excerpt":"It is not only the non-classical norbornyl cation that has proved controversial in the past. A colleague mentioned at lunch (thanks Paul!) that tri-coordinate group 14 cations such as R3Si+ have also had an interesting history. Here I take a brief look at some of these systems. Their initial characterisations,\u2026","rel":"","context":"In "crystal_structure_mining"","block_context":{"text":"crystal_structure_mining","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=1745"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/03\/164-1024x748.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":12115,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=12115","url_meta":{"origin":11757,"position":4},"title":"Aromatic electrophilic substitution. A different light on the bromination of benzene.","author":"Henry Rzepa","date":"March 12, 2014","format":false,"excerpt":"My previous post related to the aromatic electrophilic substitution of benzene using as electrophile phenyl diazonium chloride. Another prototypical reaction, and again one where benzene is too inactive for the reaction to occur easily, is the catalyst-free bromination of benzene to give bromobenzene and HBr.\u00a0 The \"text-book\" mechanism involves nucleophilic\u2026","rel":"","context":"In "Interesting chemistry"","block_context":{"text":"Interesting chemistry","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=4"},"img":{"alt_text":"br2+benzene","src":"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2014\/03\/br2+benzene.svg","width":350,"height":200},"classes":[]},{"id":15048,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=15048","url_meta":{"origin":11757,"position":5},"title":"I’ve started so I’ll finish. The mechanism of diazo coupling to indoles – forty (three) years on!","author":"Henry Rzepa","date":"December 24, 2015","format":false,"excerpt":"The BBC TV quiz series Mastermind\u00a0was first broadcast in the UK in 1972,\u00a0the same time\u00a0I was starting to investigate\u00a0the mechanism of diazocoupling to substituted indoles as part of my Ph.D. researches. The BBC program became known\u00a0for the\u00a0catch phrase\u00a0I've started so I'll finish;\u00a0here I will try to follow this precept with\u2026","rel":"","context":"In "Historical"","block_context":{"text":"Historical","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=565"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]}],"jetpack_likes_enabled":false,"authors":[{"term_id":2661,"user_id":1,"is_guest":0,"slug":"admin","display_name":"Henry Rzepa","avatar_url":"https:\/\/secure.gravatar.com\/avatar\/897b6740f7f599bca7942cdf7d7914af5988937ae0e3869ab09aebb87f26a731?s=96&d=blank&r=g","0":null,"1":"","2":"","3":"","4":"","5":"","6":"","7":"","8":""}],"_links":{"self":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/11757","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcomments&post=11757"}],"version-history":[{"count":28,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/11757\/revisions"}],"predecessor-version":[{"id":12020,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/11757\/revisions\/12020"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=11757"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=11757"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=11757"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=11757"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}