{"id":31375,"date":"2026-05-14T09:23:39","date_gmt":"2026-05-14T08:23:39","guid":{"rendered":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=31375"},"modified":"2026-05-14T14:23:49","modified_gmt":"2026-05-14T13:23:49","slug":"a-breakthrough-in-molecular-solar-thermal-most-energy-storage-dewar-pyrimidone","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=31375","title":{"rendered":"A breakthrough in Molecular Solar Thermal (MOST) energy storage &#8211; Dewar Pyrimidone."},"content":{"rendered":"<div class=\"kcite-section\" kcite-section-id=\"31375\">\n<p><strong>MOST<\/strong> is a chemical method of converting photonic or light energy into storable thermal energy which can be released on demand. A recent breakthrough in such methods has been reported<span id=\"cite_ITEM-31375-0\" name=\"citation\"><a href=\"#ITEM-31375-0\">[1]<\/a><\/span> in which a pyrimidone molecule is efficiently converted by 310nm light into the isomeric Dewar pyrimidone. This molecule is thermally stable, but when protonated, rapidly releases thermal (enthalpic) energy in converting down to protonated pyrimidone &#8211; the energy release is sufficiently rapid that it can boil water and reaching energy storage levels previously inaccessible to MOST systems. The basic chemistry is shown below &#8211; treatment with base makes it fully cyclic.<br \/>\n<a href=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2026\/05\/pyrimidone.svg\"><img decoding=\"async\" class=\"aligncenter size-full wp-image-31377\" src=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2026\/05\/pyrimidone.svg\" alt=\"\" width=\"400\" \/><\/a><br \/>\nThe chemical reactions are interesting. The light catalysed step is a pericyclic electrocyclic reaction, allowed by the Woodward-Hoffmann rules with stereochemical disrotation <em>via<\/em> suprafacial bond formation. The acid catalysed thermal reaction however, in order to conform to these rules, would nominally need to be an\u00a0electrocycic ring opening with an antarafacial stereochemical component. This would require the bicyclic ring system to contain a <em>trans<\/em> rather than the<em>\u00a0cis <\/em>bridgehead stereochemistry shown above.This reaction was first studied many years ago<span id=\"cite_ITEM-31375-1\" name=\"citation\"><a href=\"#ITEM-31375-1\">[2]<\/a><\/span> when it was shown that the thermal ring opening of\u00a0a <em>cis<\/em> Dewar isomer indeed has a high barrier, due<em> to its &#8220;forbidden<\/em>&#8221; character. This imparts one of the desirable characteristics of a <strong>MOST<\/strong> system, namely the ability to store the high energy compound if necessary for long periods of time. The key step in the above is recognising that protonating the bicyclic nitrogen of the Dewar form should significantly reduce the barrier to ring opening. Here to illustrate these two reactions, I show intrinsic reaction coordinates (IRCs) for both steps.<\/p>\n<p><a href=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2026\/05\/pyrimidone-TS-E.svg\"><img decoding=\"async\" class=\"aligncenter size-full wp-image-31389\" src=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2026\/05\/pyrimidone-TS-E.svg\" alt=\"\" width=\"540\" \/><\/a><\/p>\n<p>The calculated free energy of activation \u0394G<sub>298<\/sub><sup>\u2021<\/sup> for ring opening of the neutral form is 32.9 kcal\/mol (\u03c9B97XD\/Def2-TZVPP\/SCRF=DMF).<span id=\"cite_ITEM-31375-2\" name=\"citation\"><a href=\"#ITEM-31375-2\">[3]<\/a><\/span> which corresponds to a very slow thermal reaction (= storable). This reaction has no biradical character along the entire IRC.<\/p>\n<p><a href=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2026\/05\/pyrimidone-TS-P-E.svg\"><img decoding=\"async\" class=\"aligncenter size-full wp-image-31392\" src=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2026\/05\/pyrimidone-TS-P-E.svg\" alt=\"\" width=\"540\" \/><\/a><br \/>\n\u0394G<sub>298<\/sub><sup>\u2021<\/sup> is reduced to 15.5 kcal\/mol for the protonated form (above), a very substantial reduction and corresponding to a rapid thermal and even more exothermic reaction. The &#8220;forbidden&#8221; nature of the electrocyclic ring opening is greatly reduced &#8211; perhaps it counts as one of lowest energy forbidden pericyclic reactions to ever have been observed? This example also nicely shows<span id=\"cite_ITEM-31375-0\" name=\"citation\"><a href=\"#ITEM-31375-0\">[1]<\/a><\/span> how the system can be quickly optimised by varying substituents using quantum DFT modelling for both its exothermic character and its neutral and protonated barriers to ring opening.<\/p>\n<h2>References<\/h2>\n    <ol class=\"kcite-bibliography csl-bib-body\"><li id=\"ITEM-31375-0\">H.P.Q. Nguyen, A.J. Maertens, B.A. Baker, N.M. Wu, Z. Ye, Q. Zhou, Q. Qiu, N. Kaur, D.B. Berkinsky, K.E. Shulenberger, K.N. Houk, and G.G.D. Han, \"Molecular solar thermal energy storage in Dewar pyrimidone beyond 1.6 megajoules per kilogram\", <i>Science<\/i>, vol. 392, 2026. <a href=\"https:\/\/doi.org\/10.1126\/science.aec6413\">https:\/\/doi.org\/10.1126\/science.aec6413<\/a>\n\n<\/li>\n<li id=\"ITEM-31375-1\">M.J.S. Dewar, G.P. Ford, and H.S. Rzepa, \"Electrocyclic ring opening of 1\u03b1,4\u03b1- and 1\u03b1,4\u03b2-bicyclo[2.2.0]hexa-2,5-dienes (cis and trans Dewar benzenes): MNDO (modified neglect of diatomic overlap) semiempirical molecular orbital calculations\", <i>J. Chem. Soc., Chem. Commun.<\/i>, pp. 728-730, 1977. <a href=\"https:\/\/doi.org\/10.1039\/c39770000728\">https:\/\/doi.org\/10.1039\/c39770000728<\/a>\n\n<\/li>\n<li id=\"ITEM-31375-2\">H. Rzepa, \"A breakthrough in Molecular Solar Thermal (MOST) energy storage - Dewar Pyrimidone.\", 2026. <a href=\"https:\/\/doi.org\/10.14469\/hpc\/15935\">https:\/\/doi.org\/10.14469\/hpc\/15935<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> <!-- kcite-section 31375 -->","protected":false},"excerpt":{"rendered":"<p>MOST is a chemical method of converting photonic or light energy into storable thermal energy which can be released on demand. A recent breakthrough in such methods has been reported in which a pyrimidone molecule is efficiently converted by 310nm light into the isomeric Dewar pyrimidone. This molecule is thermally stable, but when protonated, rapidly [&hellip;]<\/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_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},"categories":[4],"tags":[],"ppma_author":[2661],"class_list":["post-31375","post","type-post","status-publish","format-standard","hentry","category-interesting-chemistry"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.6 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>A breakthrough in Molecular Solar Thermal (MOST) energy storage - Dewar Pyrimidone. - 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=31375\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"A breakthrough in Molecular Solar Thermal (MOST) energy storage - Dewar Pyrimidone. - Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"og:description\" content=\"MOST is a chemical method of converting photonic or light energy into storable thermal energy which can be released on demand. A recent breakthrough in such methods has been reported in which a pyrimidone molecule is efficiently converted by 310nm light into the isomeric Dewar pyrimidone. This molecule is thermally stable, but when protonated, rapidly [&hellip;]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=31375\" \/>\n<meta property=\"og:site_name\" content=\"Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"article:published_time\" content=\"2026-05-14T08:23:39+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2026-05-14T13:23:49+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":"A breakthrough in Molecular Solar Thermal (MOST) energy storage - Dewar Pyrimidone. - 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=31375","og_locale":"en_GB","og_type":"article","og_title":"A breakthrough in Molecular Solar Thermal (MOST) energy storage - Dewar Pyrimidone. - Henry Rzepa&#039;s Blog","og_description":"MOST is a chemical method of converting photonic or light energy into storable thermal energy which can be released on demand. 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This molecule is thermally stable, but when protonated, rapidly [&hellip;]","og_url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=31375","og_site_name":"Henry Rzepa&#039;s Blog","article_published_time":"2026-05-14T08:23:39+00:00","article_modified_time":"2026-05-14T13:23:49+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=31375#article","isPartOf":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=31375"},"author":{"name":"Henry Rzepa","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/#\/schema\/person\/2b40f7b9c872a4dc1547e040a11b6281"},"headline":"A breakthrough in Molecular Solar Thermal (MOST) energy storage &#8211; Dewar Pyrimidone.","datePublished":"2026-05-14T08:23:39+00:00","dateModified":"2026-05-14T13:23:49+00:00","mainEntityOfPage":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=31375"},"wordCount":427,"commentCount":0,"image":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=31375#primaryimage"},"thumbnailUrl":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2026\/05\/pyrimidone.svg","articleSection":["Interesting chemistry"],"inLanguage":"en-GB","potentialAction":[{"@type":"CommentAction","name":"Comment","target":["https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=31375#respond"]}]},{"@type":"WebPage","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=31375","url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=31375","name":"A breakthrough in Molecular Solar Thermal (MOST) energy storage - Dewar Pyrimidone. - Henry Rzepa&#039;s Blog","isPartOf":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/#website"},"primaryImageOfPage":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=31375#primaryimage"},"image":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=31375#primaryimage"},"thumbnailUrl":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2026\/05\/pyrimidone.svg","datePublished":"2026-05-14T08:23:39+00:00","dateModified":"2026-05-14T13:23:49+00:00","author":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/#\/schema\/person\/2b40f7b9c872a4dc1547e040a11b6281"},"breadcrumb":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=31375#breadcrumb"},"inLanguage":"en-GB","potentialAction":[{"@type":"ReadAction","target":["https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=31375"]}]},{"@type":"ImageObject","inLanguage":"en-GB","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=31375#primaryimage","url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2026\/05\/pyrimidone.svg","contentUrl":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2026\/05\/pyrimidone.svg"},{"@type":"BreadcrumbList","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=31375#breadcrumb","itemListElement":[{"@type":"ListItem","position":1,"name":"Home","item":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog"},{"@type":"ListItem","position":2,"name":"A breakthrough in Molecular Solar Thermal (MOST) energy storage &#8211; 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It has now been detected in the atmosphere of Titan, one of Saturn's moons and joins benzene, another aromatic molecule together with the protonated version of cyclopropenylidene, C3H3+ also\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":5991,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=5991","url_meta":{"origin":31375,"position":1},"title":"Violations. There are none!  Part 2.","author":"Henry Rzepa","date":"December 26, 2011","format":false,"excerpt":"I left the story of the molecule below on the precipice of a cliff. I had shaved off the four benzo groups (blue) in the time honoured computational tradition of clearing away distractions. Unfortunately, it became clear as the story unfolded that the benzo groups had a distractingly critical role\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":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/12\/86-dibenzo.svg","width":350,"height":200},"classes":[]},{"id":22571,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=22571","url_meta":{"origin":31375,"position":2},"title":"Question for the day &#8211; Einstein, special relativity and atomic weights.","author":"Henry Rzepa","date":"July 25, 2020","format":false,"excerpt":"Sometimes a (scientific) thought just pops into one's mind. Most are probably best not shared with anyone, but since its the summer silly season, I thought I might with this one. Famously, according to Einstein, m \u00a0= E\/c^^2, the equivalence of energy to mass. Consider a typical exoenergic chemical reaction:\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":10237,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=10237","url_meta":{"origin":31375,"position":3},"title":"How to predict the regioselectivity of epoxide ring opening.","author":"Henry Rzepa","date":"April 28, 2013","format":false,"excerpt":"I recently got an email from a student asking about the best way of rationalising epoxide ring opening using some form of molecule orbitals. This reminded me of the famous experiment involving propene epoxide. In the presence of 0.3% NaOH, propene epoxide reacts with ethanol at the unsubstituted carbon (~82%\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":9135,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=9135","url_meta":{"origin":31375,"position":4},"title":"Why is N,O-diphenyl hydroxylamine (PhNHOPh) unknown?","author":"Henry Rzepa","date":"January 16, 2013","format":false,"excerpt":"If you search e.g. Scifinder for N,O-diphenyl hydroxylamine (RN\u00a024928-98-1) there is just one literature citation, to a 1962 patent. Nothing else; not even a calculation (an increasing proportion of the molecules reported in Chemical Abstracts have now only ever been subjected to calculation, not synthesis).\u00a0A search of Reaxys also offers\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":14740,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=14740","url_meta":{"origin":31375,"position":5},"title":"How to stop (some) acetals hydrolysing.","author":"Henry Rzepa","date":"November 12, 2015","format":false,"excerpt":"Derek Lowe has a recent post entitled \"Another Funny-Looking Structure Comes Through\". He cites a recent medchem article in which the following acetal sub-structure appears in a promising drug candidate (blue component below). His point is that orally taken drugs have to survive acid (green below) encountered in the stomach,\u2026","rel":"","context":"In &quot;reaction mechanism&quot;","block_context":{"text":"reaction mechanism","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=1086"},"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\/31375","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=31375"}],"version-history":[{"count":18,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/31375\/revisions"}],"predecessor-version":[{"id":31409,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/31375\/revisions\/31409"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=31375"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=31375"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=31375"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=31375"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}