{"id":19569,"date":"2018-04-18T07:58:23","date_gmt":"2018-04-18T06:58:23","guid":{"rendered":"https:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=19569"},"modified":"2018-08-13T14:15:15","modified_gmt":"2018-08-13T13:15:15","slug":"aromaticity-induced-basicity","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=19569","title":{"rendered":"Aromaticity-induced basicity."},"content":{"rendered":"<div class=\"kcite-section\" kcite-section-id=\"19569\">\n<p>The molecules below were discussed in the previous post as examples of highly polar but formally neutral molecules, a property induced by aromatisation of up to three rings. Since <em>e.g.<\/em> compound <strong>3<\/strong> is known only in its protonated phenolic form, here I take a look at the basicity of the oxygen in these systems to see if deprotonation of the ionic phenol form to the neutral polar form is viable.<\/p>\n<p><a href=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2018\/04\/sb1-page001.svg\"><img decoding=\"async\" class=\"aligncenter size-large wp-image-19561\" src=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2018\/04\/sb1-page001.svg\" alt=\"\" width=\"350\" \/><\/a><\/p>\n<p>The equilibrium being considered is shown below for compound <strong>2<\/strong>:<a href=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2018\/04\/sb3-page001.svg\"><img decoding=\"async\" class=\"aligncenter size-large wp-image-19573\" src=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2018\/04\/sb3-page001.svg\" alt=\"\" width=\"300\" \/><\/a><\/p>\n<p>The energetics of this equilibrium shown below, computed at the \u03c9B97XD\/Def2-TZVPPD\/SCRF=water level and for which the FAIR data DOI is\u00a0<a href=\"https:\/\/doi.org\/10.14469\/hpc\/4073\">10.14469\/hpc\/4073<\/a><\/p>\n<p>For <strong>1: X=Cl<\/strong>, the energy is shown below as a function of the O&#8230;.H distance. Proton abstraction from HCl is exothermic by ~25 kcal\/mol.<\/p>\n<p><a href=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2018\/04\/OHCl.svg\"><img decoding=\"async\" class=\"aligncenter size-large wp-image-19570\" src=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2018\/04\/OHCl.svg\" alt=\"\" width=\"450\" \/><\/a> For <strong>2: X=Cl<\/strong>, the exothermicity increases by only ~5 kcal\/mol , despite the apparent aromatisation of a further ring. It is also worth noting that this is greater basicity than that of <strong>e.g.<\/strong> water, where around 4-5 water molecules acting in concert <a href=\"https:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=15924\">are required<\/a> to deprotonate HCl.<a href=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2018\/04\/2_HCl.svg\"><img decoding=\"async\" class=\"aligncenter size-large wp-image-19585\" src=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2018\/04\/2_HCl.svg\" alt=\"\" width=\"450\" \/><\/a>For <strong>1: X=OH<\/strong>, the proton abstraction from water is mildly endothermic by about 13 kcal\/mol; indeed there is no energy minimum for carbonyl protonation and instead a relatively strong hydrogen bond to the water is formed instead.<br \/>\n <a href=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2018\/04\/HOH.svg\"><img decoding=\"async\" class=\"aligncenter size-large wp-image-19579\" src=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2018\/04\/HOH.svg\" alt=\"\" width=\"450\" \/><\/a><\/p>\n<p>For <strong>2: X=OH<\/strong> the endothermicity is reduced to ~9 kcal\/mol.<a href=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2018\/04\/2_HOH.svg\"><img decoding=\"async\" class=\"aligncenter size-large wp-image-19587\" src=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2018\/04\/2_HOH.svg\" alt=\"\" width=\"450\" \/><\/a><\/p>\n<p>For <strong>1: X=CH<sub>3<\/sub><\/strong>, deprotonation of methane is now strongly endothermic by ~40 kcal\/mol.<\/p>\n<p><img decoding=\"async\" class=\"aligncenter size-large wp-image-19571\" src=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2018\/04\/OHCH3.svg\" alt=\"\" width=\"450\" \/><\/p>\n<p>So the molecules <strong>1 &#8211; 2<\/strong> above are clearly not superbases,\u00a0which perhaps augers well for being able to deprotonate the ionic phenols into these neutral but highly polar molecules.<\/p>\n<!-- kcite active, but no citations found -->\n<\/div> <!-- kcite-section 19569 -->","protected":false},"excerpt":{"rendered":"<p>The molecules below were discussed in the previous post as examples of highly polar but formally neutral molecules, a property induced by aromatisation of up to three rings. Since e.g. compound 3 is known only in its protonated phenolic form, here I take a look at the basicity of the oxygen in these systems to [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"jetpack_post_was_ever_published":false,"_jetpack_newsletter_access":"","_jetpack_dont_email_post_to_subs":false,"_jetpack_newsletter_tier_id":0,"_jetpack_memberships_contains_paywalled_content":false,"_jetpack_memberships_contains_paid_content":false,"activitypub_content_warning":"","activitypub_content_visibility":"","activitypub_max_image_attachments":5,"activitypub_interaction_policy_quote":"anyone","activitypub_status":"","footnotes":"","jetpack_publicize_message":"","jetpack_publicize_feature_enabled":true,"jetpack_social_post_already_shared":true,"jetpack_social_options":{"image_generator_settings":{"template":"highway","default_image_id":0,"font":"","enabled":false},"version":2}},"categories":[4],"tags":[2460,2117,1395,24,2462,1960,1966,2461,1473],"ppma_author":[2661],"class_list":["post-19569","post","type-post","status-publish","format-standard","hentry","category-interesting-chemistry","tag-antiseptics","tag-aromatization","tag-chemistry","tag-energy","tag-energy-minimum","tag-hydrogen","tag-molecule","tag-neurotoxins","tag-science"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.5 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Aromaticity-induced basicity. - Henry Rzepa&#039;s Blog<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=19569\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Aromaticity-induced basicity. - Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"og:description\" content=\"The molecules below were discussed in the previous post as examples of highly polar but formally neutral molecules, a property induced by aromatisation of up to three rings. Since e.g. compound 3 is known only in its protonated phenolic form, here I take a look at the basicity of the oxygen in these systems to [&hellip;]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=19569\" \/>\n<meta property=\"og:site_name\" content=\"Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"article:published_time\" content=\"2018-04-18T06:58:23+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2018-08-13T13:15:15+00:00\" \/>\n<meta property=\"og:image\" content=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2018\/04\/sb1-page001.svg\" \/>\n<meta name=\"author\" content=\"Henry Rzepa\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"Henry Rzepa\" \/>\n\t<meta name=\"twitter:label2\" content=\"Estimated reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"1 minute\" \/>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"Aromaticity-induced basicity. - Henry Rzepa&#039;s Blog","robots":{"index":"index","follow":"follow","max-snippet":"max-snippet:-1","max-image-preview":"max-image-preview:large","max-video-preview":"max-video-preview:-1"},"canonical":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=19569","og_locale":"en_GB","og_type":"article","og_title":"Aromaticity-induced basicity. - Henry Rzepa&#039;s Blog","og_description":"The molecules below were discussed in the previous post as examples of highly polar but formally neutral molecules, a property induced by aromatisation of up to three rings. 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The energetic outcome of my\u00a0model matched the known equilbrium in water as favouring the unprotonated form (pKb ~4.75). I add here two amines for which\u00a0R=Me3Si and R=CN. The idea is that the first will assist\u2026","rel":"","context":"In &quot;General&quot;","block_context":{"text":"General","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=1"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]},{"id":19550,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=19550","url_meta":{"origin":19569,"position":1},"title":"A record polarity for a neutral compound?","author":"Henry Rzepa","date":"April 13, 2018","format":false,"excerpt":"In several posts a year or so ago I considered various suggestions for the most polar neutral molecules, as measured by the dipole moment. A record had been claimed for a synthesized molecule of ~14.1\u00b10.7D. I pushed this to a calculated 21.7D for an admittedly hypothetical and unsynthesized molecule. Here\u2026","rel":"","context":"In &quot;Interesting chemistry&quot;","block_context":{"text":"Interesting chemistry","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=4"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]},{"id":21472,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=21472","url_meta":{"origin":19569,"position":2},"title":"The Structure of Tetrodotoxin as a free base &#8211; with a better solvation model.","author":"Henry Rzepa","date":"November 26, 2019","format":false,"excerpt":"In the previous post, I discussed the structure of the free base form of tetrodotoxin, often represented as originally suggested by Woodward below in an ionic form: Quantum calculations suggested that this form was higher in energy than neutral forms devoid of the zwitterionic charge separation in a relatively non\u2026","rel":"","context":"In &quot;Interesting chemistry&quot;","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\/2019\/11\/zw3H2O-1024x770.jpg?resize=350%2C200&ssl=1","width":350,"height":200},"classes":[]},{"id":18058,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=18058","url_meta":{"origin":19569,"position":3},"title":"Cyclopropenium cyclopentadienide: a strangely neutral ion-pair?","author":"Henry Rzepa","date":"April 9, 2017","format":false,"excerpt":"Both the cyclopropenium cation and the cyclopentadienide anion are well-known 4n+2-type aromatic ions, but could the two together form an ion-pair? A search of the Cambridge structure database reveals 52 instances of the cyclopropenium cation with a variety of counter-anions, 77 cyclopentadienide\u00a0anions with a variety of counter-cations and one (SOWMOG,\u2026","rel":"","context":"In &quot;crystal_structure_mining&quot;","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\/04\/SOWMOG-1002x1024.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":17349,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=17349","url_meta":{"origin":19569,"position":4},"title":"Forming a stabilized m-benzyne.","author":"Henry Rzepa","date":"January 20, 2017","format":false,"excerpt":"The story so far. Inspired by the report of the most polar neutral compound yet made, I suggested some candidates based on the azulene ring system that if made might be even more polar. This then led to considering a smaller \u03c0-analogue of azulene, m-benzyne. Here I ponder how a\u2026","rel":"","context":"In &quot;Interesting chemistry&quot;","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\/2017\/01\/polar-Cla.gif?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":24027,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=24027","url_meta":{"origin":19569,"position":5},"title":"Molecules with very large dipole moments: cyclopropenium acetylide","author":"Henry Rzepa","date":"July 11, 2021","format":false,"excerpt":"Occasionally, someone comments about an old post here, asking a question. Such was the case here, when a question about the dipole moment of cyclopropenylidene arose. It turned out to be 3.5D, but this question sparked a thought about the related molecule below. Of the two resonance forms show above,\u2026","rel":"","context":"In &quot;Interesting chemistry&quot;","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\/2021\/07\/C5H5-esp-1024x690.jpg?resize=350%2C200&ssl=1","width":350,"height":200},"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\/19569","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=19569"}],"version-history":[{"count":18,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/19569\/revisions"}],"predecessor-version":[{"id":19593,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/19569\/revisions\/19593"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=19569"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=19569"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=19569"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=19569"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}