{"id":32506,"date":"2026-11-09T15:03:28","date_gmt":"2026-11-09T15:03:28","guid":{"rendered":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32506"},"modified":"2026-11-09T15:03:28","modified_gmt":"2026-11-09T15:03:28","slug":"molecules-of-the-year-2026-a-hydroxy%e2%80%90substituted-trialkyloxonium-ion-and-its-oxonium-alkoxide-zwitterion","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32506","title":{"rendered":"Molecules of the year: 2026 – “\u2018A Hydroxy\u2010Substituted Trialkyloxonium Ion and Its Oxonium Alkoxide Zwitterion”"},"content":{"rendered":"
\n

This candidate[1]<\/a><\/span> for “MOTY 2026” has the unusual feature of containing both a trialkyl oxonium cation and an alkoxide counterion present in the same species (11z<\/strong> below).<\/p>\n

\"\"<\/a>
\nEvidence for the presence of 11z\u00a0<\/strong>came from the 1<\/sup> NMR spectra of 11<\/strong> in the presence of the non-nucleophilic base t-butyl tetramethylguanidine (Barton’s base or BB) which showed shifts in the base consistent with its protonation and smaller but significant shifts (as well as changes in the coupling constants) in the oxatriquinane component, commensurate with the formation of the zwitterion 11z<\/strong>. These effects were not observed when 11<\/strong> was methylated (preventing deprotonation). The zwitterion 11z<\/strong> was however very unstable, decomposing at temperatures of above -60C.<\/p>\n

My interest in these species originates in the report of a “concerted triple H-tunneling mechanism”[2]<\/a><\/span> in which three protons move in concert as part of a cyclic transition state, or a related question of mine posed in 2011\u00a0– “Do electrons prefer to move in packs of 4, 6 or 8 during proton exchange in a calixarene?”[3]<\/a><\/span> This latter example has a set of four OH groups, exchanging protons in a cyclic manner and I found that in the very non-polar benzene as a solvent, the synchronous exchange of the four protons was comuted to not be a genuine transition state, (one negative force constant) but a higher order stationary point with three negative force constants.\u00a0Not noted at the time but worth pointing out now is the cyclic exchange of four protons is an 8-electron process which might be expected to be a \u03c3-antiaromatic system, and hence disfavoured.<\/p>\n

So what of the proton exchange in\u00a0the smaller ring 11<\/strong>. This is now a 6-electron process, nominally \u03c3-aromatic and hence more favoured? An \u03c9B97XD\/Def2-TZVPP\/CPCM=thf calculation[4]<\/a><\/span> shows that in contracts to the 8-electron homologue, this is a true concerted synchronous process (Figure 1, \u03bd 1875i<\/i> cm-1<\/sup>) as illustrated by an IRC (Figure 2).[5]<\/a><\/span>
\n\"\"
\nFigure 1.
\n\"\"<\/a>
\nFigure 2.<\/p>\n

One major difference between the tetradiol calixarene[6]<\/a><\/span> and the present tri-diol triquinane is the barrier to proton exchange, the latter being significantly higher (ΔG 24.88 kcal\/mol[7]<\/a><\/span>) than the former (ΔG ~14 kcal\/mol). This is probably due to the smaller and hence unfavourable H-O-H angles (83.8\u00b0) and non-linear O-H-O angles (154°) induced by the smaller ring size. One interesting aspect of this transition state is revealed by an\u00a0NCI (non-covalent-interaction) analysis (Figure 3, click on image to get 3D interactive model) showing weak dispersion-like stabilisations between the transferring protons and C-H hydrogens of the cage, as well as a mysterious attractive dispersion feature in the centre of the cage.<\/p>\n

\"\"
\nFigure 3.<\/p>\n

What is needed is some experimental verification of the above prediction, perhaps using a desymmetrised oxatriquinane 11<\/b> and perchance use of isotope effects to investigate any concerted nature for the process.<\/p>\n

References<\/h2>\n
  1. A.L. Otsuki, G.A. Alkan, S. Manabe, W.T. Shewa, G. Gunbas, J.C. Fettinger, M. Mascal, and N. Hafezi, \"A Hydroxy\u2010Substituted Trialkyloxonium Ion and Its Oxonium Alkoxide Zwitterion\", Angewandte Chemie International Edition<\/i>, vol. 65, 2026. https:\/\/doi.org\/10.1002\/anie.2727232<\/a>\n\n<\/li>\n
  2. H. Rzepa, \"Reinvestigating the reported transition state structure of a concerted triple H-tunneling mechanism.\", 2025. https:\/\/doi.org\/10.59350\/qgwfn-rsc92<\/a>\n\n<\/li>\n
  3. H. Rzepa, \"Do electrons prefer to move in packs of 4, 6 or 8 during proton exchange in a calixarene?\", 2011. https:\/\/doi.org\/10.59350\/9xed3-sy403<\/a>\n\n<\/li>\n
  4. H. Rzepa, \"Oxonium cation, 11 G = -652.500883\", 2026. https:\/\/doi.org\/10.5281\/zenodo.23921575<\/a>\n\n<\/li>\n
  5. H. Rzepa, \"Oxonium cation, 11 IRC\", 2026. https:\/\/doi.org\/10.5281\/zenodo.23919051<\/a>\n\n<\/li>\n
  6. H. Rzepa, \"Oxonium cation, 11 IRC => starting state G = -652.540534\", 2026. https:\/\/doi.org\/10.5281\/zenodo.24086130<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> ","protected":false},"excerpt":{"rendered":"

    This candidate for “MOTY 2026” has the unusual feature of containing both a trialkyl oxonium cation and an alkoxide counterion present in the same species (11z below). Evidence for the presence of 11z\u00a0came from the 1 NMR spectra of 11 in the presence of the non-nucleophilic base t-butyl tetramethylguanidine (Barton’s base or BB) which showed […]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_jetpack_newsletter_access":"","_jetpack_dont_email_post_to_subs":false,"_jetpack_newsletter_tier_id":0,"_jetpack_memberships_contains_paywalled_content":false,"_jetpack_hide_featured_image":false,"_jetpack_featured_image_duplicate_dismissed":0,"_jetpack_feature_clip_id":0,"_jetpack_memberships_contains_paid_content":false,"activitypub_content_warning":"","activitypub_content_visibility":"","activitypub_max_image_attachments":5,"activitypub_interaction_policy_quote":"anyone","activitypub_status":"federated","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},"jetpack_post_was_ever_published":false,"_ppma_block_editor_authors":""},"categories":[4],"tags":[],"ppma_author":[2661],"class_list":["post-32506","post","type-post","status-publish","format-standard","hentry","category-interesting-chemistry"],"yoast_head":"\nMolecules of the year: 2026 - "\u2018A Hydroxy\u2010Substituted Trialkyloxonium Ion and Its Oxonium Alkoxide Zwitterion" - Henry Rzepa'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=32506\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Molecules of the year: 2026 - "\u2018A Hydroxy\u2010Substituted Trialkyloxonium Ion and Its Oxonium Alkoxide Zwitterion" - Henry Rzepa's Blog\" \/>\n<meta property=\"og:description\" content=\"This candidate for “MOTY 2026” has the unusual feature of containing both a trialkyl oxonium cation and an alkoxide counterion present in the same species (11z below). Evidence for the presence of 11z\u00a0came from the 1 NMR spectra of 11 in the presence of the non-nucleophilic base t-butyl tetramethylguanidine (Barton’s base or BB) which showed […]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32506\" \/>\n<meta property=\"og:site_name\" content=\"Henry Rzepa's Blog\" \/>\n<meta property=\"article:published_time\" content=\"2026-11-09T15:03:28+00:00\" \/>\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=\"3 minutes\" \/>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"Molecules of the year: 2026 - \"\u2018A Hydroxy\u2010Substituted Trialkyloxonium Ion and Its Oxonium Alkoxide Zwitterion\" - Henry Rzepa'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=32506","og_locale":"en_GB","og_type":"article","og_title":"Molecules of the year: 2026 - \"\u2018A Hydroxy\u2010Substituted Trialkyloxonium Ion and Its Oxonium Alkoxide Zwitterion\" - Henry Rzepa's Blog","og_description":"This candidate for “MOTY 2026” has the unusual feature of containing both a trialkyl oxonium cation and an alkoxide counterion present in the same species (11z below). Evidence for the presence of 11z\u00a0came from the 1 NMR spectra of 11 in the presence of the non-nucleophilic base t-butyl tetramethylguanidine (Barton’s base or BB) which showed […]","og_url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32506","og_site_name":"Henry Rzepa's Blog","article_published_time":"2026-11-09T15:03:28+00:00","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=32506#article","isPartOf":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32506"},"author":{"name":"Henry Rzepa","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/#\/schema\/person\/2b40f7b9c872a4dc1547e040a11b6281"},"headline":"Molecules of the year: 2026 – “\u2018A Hydroxy\u2010Substituted Trialkyloxonium Ion and Its Oxonium Alkoxide Zwitterion”","datePublished":"2026-11-09T15:03:28+00:00","mainEntityOfPage":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32506"},"wordCount":490,"commentCount":0,"image":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32506#primaryimage"},"thumbnailUrl":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2026\/11\/11.svg","articleSection":["Interesting chemistry"],"inLanguage":"en-GB","potentialAction":[{"@type":"CommentAction","name":"Comment","target":["https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32506#respond"]}]},{"@type":"WebPage","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32506","url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32506","name":"Molecules of the year: 2026 - 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This is an application of Hammond's postulate[ in extrapolating the properties of a\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\/05\/hidden-intermediate-1.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":21436,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=21436","url_meta":{"origin":32506,"position":1},"title":"The Structure of Tetrodotoxin as a free base.","author":"Henry Rzepa","date":"November 9, 2019","format":false,"excerpt":"The notorious neurotoxin Tetrodotoxin is often chemically represented as a zwitterion, shown below as 1. This idea seems to originate from a famous article written in 1964 by the legendary organic chemist, Robert Burns Woodward. This structure has propagated on to Wikipedia and is found in many other sources. With\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\/2019\/11\/MEP-1024x749.jpg?resize=350%2C200&ssl=1","width":350,"height":200},"classes":[]},{"id":10367,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=10367","url_meta":{"origin":32506,"position":2},"title":"Transition states for the (base) catalysed ring opening of propene epoxide.","author":"Henry Rzepa","date":"May 8, 2013","format":false,"excerpt":"The previous post described how the acid catalysed ring opening of propene epoxide by an alcohol (methanol) is preceded by pre-protonation of the epoxide oxygen to form a \"hidden intermediate\" on the concerted intrinsic reaction pathway to ring opening. Here I take a look at the mechanism where a strong\u2026","rel":"","context":"In \"Reaction Mechanism\"","block_context":{"text":"Reaction Mechanism","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?tag=reaction-mechanism"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]},{"id":17279,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=17279","url_meta":{"origin":32506,"position":3},"title":"The dipole moments of highly polar molecules: glycine zwitterion.","author":"Henry Rzepa","date":"December 24, 2016","format":false,"excerpt":"The previous posts produced discussion about the dipole moments of highly polar molecules. Here to produce some reference points for further discussion I look at the dipole moment of glycine, the classic\u00a0zwitterion (an internal ion-pair). Dielectric relaxation studies of glycine-water mixtures yield values that range from\u00a015.7D to 11.9D although these\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\/2016\/12\/051.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":32470,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32470","url_meta":{"origin":32506,"position":4},"title":"Molecules of the year: 2026 – vote!","author":"Henry Rzepa","date":"October 29, 2026","format":false,"excerpt":"The annual C&E News poll on \"molecules of the year\" is under way and you are encouraged to vote for one. Having taken a quick look at each of the candidates, I normally see if I can add any \"value\" to the originals by performing appropriate calculations (e.g. and many\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":"","width":0,"height":0},"classes":[]},{"id":3392,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=3392","url_meta":{"origin":32506,"position":5},"title":"Do electrons prefer to move in packs of 4, 6 or 8 during proton exchange in a calixarene?","author":"Henry Rzepa","date":"January 7, 2011","format":false,"excerpt":"This story starts with a calixarene, a molecule (suitably adorned with substituents) frequently used as a host to entrap a guest and perchance make the guest do something interesting. Such a calixarene was at the heart of a recent story where an attempt was made to induce it to capture\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\/2011\/01\/calixarene.jpg?resize=350%2C200","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","avatar_alt":"","avatar_decorative":"","author_category":"1","first_name":"Henry","last_name":"Rzepa","user_url":"https:\/\/orcid.org\/0000-0002-8635-8390","job_title":"","description":"Emeritus Professor of Computational Chemistry at Imperial College London."}],"jetpack_featured_media_url":"","_links":{"self":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/32506","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=32506"}],"version-history":[{"count":49,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/32506\/revisions"}],"predecessor-version":[{"id":32568,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/32506\/revisions\/32568"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=32506"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=32506"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=32506"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=32506"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}