{"id":16228,"date":"2016-04-15T16:12:11","date_gmt":"2016-04-15T15:12:11","guid":{"rendered":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=16228"},"modified":"2016-06-26T08:28:02","modified_gmt":"2016-06-26T07:28:02","slug":"oxane-oxide-a-tautomer-of-hydrogen-peroxide","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=16228","title":{"rendered":"Oxane oxide:  a tautomer of hydrogen peroxide."},"content":{"rendered":"<div class=\"kcite-section\" kcite-section-id=\"16228\">\n<p>\n\tIf <span style=\"color:#0000FF;\">H<sub>3<\/sub>N<sup>+<\/sup>-O<sup>&#8211;<\/sup><\/span>&nbsp;is viable compared with its tautomer <span style=\"color:#0000FF;\">H<sub>2<\/sub>N-OH<\/span> when carrying water bridges,&nbsp;then why not try&nbsp;<span style=\"color:#0000FF;\">H<sub>2<\/sub>O<sup>+<\/sup>-O<sup>&#8211;<\/sup><\/span> <em>vs<\/em> <span style=\"color:#0000FF;\">HO-OH<\/span>?\n<\/p>\n<p>\n\tThere are no examples to be found in crystal structures!&nbsp;The&nbsp;solvated structure of&nbsp;H<sub>2<\/sub>O<sup>+<\/sup>-O<sup>&#8211;<\/sup>&nbsp;is modified directly from that of&nbsp;H<sub>3<\/sub>N<sup>+<\/sup>-O<sup>&#8211; <\/sup>and the computed (&omega;B97XD\/6-311++G(d,p)\/SCRF=water) structure<span id=\"cite_ITEM-16228-0\" name=\"citation\"><a href=\"#ITEM-16228-0\">[1]<\/a><\/span> is&nbsp;shown below. Noteworthy is that the hydrogen bonds at&nbsp;the&nbsp;O<sup>+<\/sup>&nbsp;end are&nbsp;far stronger than those to at the O<sup>&#8211;<\/sup> end.\n<\/p>\n<p>\n\t<img decoding=\"async\" alt=\"NH3-8\" class=\"aligncenter size-full wp-image-15936\" onclick=\"jmolInitialize('..\/Jmol\/','JmolAppletSigned.jar');jmolSetAppletColor('white');jmolApplet([450,450],'load wp-content\/uploads\/2016\/04\/H2O2-839.401716.log; frame 2;spin 3;');\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/04\/oxane-oxide.jpg\" width=\"300\" \/>\n<\/p>\n<p>\n\tThe corresponding hydrated hydrogen peroxide is 16.3&nbsp;kcal\/mol lower in free energy; this compares favourably with the value for water itself and suggests that oxane oxide might also be capable of isolation inside a suitable hydrogen bond stabilising cavity.<\/p>\n<h2>References<\/h2>\n    <ol class=\"kcite-bibliography csl-bib-body\"><li id=\"ITEM-16228-0\">H.S. Rzepa, \"H20O11\", 2016. <a href=\"https:\/\/doi.org\/10.14469\/ch\/192005\">https:\/\/doi.org\/10.14469\/ch\/192005<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> <!-- kcite-section 16228 -->","protected":false},"excerpt":{"rendered":"<p>If H3N+-O&#8211;&nbsp;is viable compared with its tautomer H2N-OH when carrying water bridges,&nbsp;then why not try&nbsp;H2O+-O&#8211; vs HO-OH? There are no examples to be found in crystal structures!&nbsp;The&nbsp;solvated structure of&nbsp;H2O+-O&#8211;&nbsp;is modified directly from that of&nbsp;H3N+-O&#8211; and the computed (&omega;B97XD\/6-311++G(d,p)\/SCRF=water) structure is&nbsp;shown below. Noteworthy is that the hydrogen bonds at&nbsp;the&nbsp;O+&nbsp;end are&nbsp;far stronger than those to at the [&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":[1,4],"tags":[1713,1830,40,1449,1831,1798,1832,1433,1833,1715],"ppma_author":[2661],"class_list":["post-16228","post","type-post","status-publish","format-standard","hentry","category-general","category-interesting-chemistry","tag-ammonia","tag-anions","tag-free-energy","tag-hydrogen-bond","tag-hydrogen-peroxide","tag-inorganic-solvents","tag-oxide","tag-oxidizing-agents","tag-peroxide","tag-properties-of-water"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.5 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Oxane oxide: a tautomer of hydrogen peroxide. - 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=16228\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Oxane oxide: a tautomer of hydrogen peroxide. - Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"og:description\" content=\"If H3N+-O&#8211;&nbsp;is viable compared with its tautomer H2N-OH when carrying water bridges,&nbsp;then why not try&nbsp;H2O+-O&#8211; vs HO-OH? There are no examples to be found in crystal structures!&nbsp;The&nbsp;solvated structure of&nbsp;H2O+-O&#8211;&nbsp;is modified directly from that of&nbsp;H3N+-O&#8211; and the computed (&omega;B97XD\/6-311++G(d,p)\/SCRF=water) structure is&nbsp;shown below. Noteworthy is that the hydrogen bonds at&nbsp;the&nbsp;O+&nbsp;end are&nbsp;far stronger than those to at the [&hellip;]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=16228\" \/>\n<meta property=\"og:site_name\" content=\"Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"article:published_time\" content=\"2016-04-15T15:12:11+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2016-06-26T07:28:02+00:00\" \/>\n<meta property=\"og:image\" content=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/04\/oxane-oxide.jpg\" \/>\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":"Oxane oxide: a tautomer of hydrogen peroxide. - 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=16228","og_locale":"en_GB","og_type":"article","og_title":"Oxane oxide: a tautomer of hydrogen peroxide. - Henry Rzepa&#039;s Blog","og_description":"If H3N+-O&#8211;&nbsp;is viable compared with its tautomer H2N-OH when carrying water bridges,&nbsp;then why not try&nbsp;H2O+-O&#8211; vs HO-OH? There are no examples to be found in crystal structures!&nbsp;The&nbsp;solvated structure of&nbsp;H2O+-O&#8211;&nbsp;is modified directly from that of&nbsp;H3N+-O&#8211; and the computed (&omega;B97XD\/6-311++G(d,p)\/SCRF=water) structure is&nbsp;shown below. Noteworthy is that the hydrogen bonds at&nbsp;the&nbsp;O+&nbsp;end are&nbsp;far stronger than those to at the [&hellip;]","og_url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=16228","og_site_name":"Henry Rzepa&#039;s Blog","article_published_time":"2016-04-15T15:12:11+00:00","article_modified_time":"2016-06-26T07:28:02+00:00","og_image":[{"url":"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/04\/oxane-oxide.jpg","type":"","width":"","height":""}],"author":"Henry Rzepa","twitter_card":"summary_large_image","twitter_misc":{"Written by":"Henry Rzepa","Estimated reading time":"1 minute"},"schema":{"@context":"https:\/\/schema.org","@graph":[{"@type":"Article","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=16228#article","isPartOf":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=16228"},"author":{"name":"Henry Rzepa","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/#\/schema\/person\/2b40f7b9c872a4dc1547e040a11b6281"},"headline":"Oxane oxide: a tautomer of hydrogen peroxide.","datePublished":"2016-04-15T15:12:11+00:00","dateModified":"2016-06-26T07:28:02+00:00","mainEntityOfPage":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=16228"},"wordCount":150,"commentCount":0,"image":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=16228#primaryimage"},"thumbnailUrl":"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/04\/oxane-oxide.jpg","keywords":["Ammonia","Anions","free energy","Hydrogen bond","Hydrogen peroxide","Inorganic solvents","Oxide","Oxidizing agents","Peroxide","Properties of water"],"articleSection":["General","Interesting chemistry"],"inLanguage":"en-GB","potentialAction":[{"@type":"CommentAction","name":"Comment","target":["https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=16228#respond"]}]},{"@type":"WebPage","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=16228","url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=16228","name":"Oxane oxide: a tautomer of hydrogen peroxide. - 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Here I explore azane oxide or H3N+-O-,\u2021\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":23410,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=23410","url_meta":{"origin":16228,"position":1},"title":"The small-molecule antiviral compound Molnupiravir: an exploration of its tautomers.","author":"Henry Rzepa","date":"March 14, 2021","format":false,"excerpt":"For obvious reasons, anti-viral molecules are very much in the news at the moment. Thus Derek Lowe highlights Molnupiravir which is shown as a hydroxylamine, the representation originating from the Wikipedia page on the molecule. I like stereocentres more clearly identified using eg R\/S notation and so I went to\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\/03\/molnupiravir-1024x639.jpg?resize=350%2C200&ssl=1","width":350,"height":200},"classes":[]},{"id":17279,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=17279","url_meta":{"origin":16228,"position":2},"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 &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\/2016\/12\/051.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":18351,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=18351","url_meta":{"origin":16228,"position":3},"title":"Tautomeric polymorphism.","author":"Henry Rzepa","date":"June 1, 2017","format":false,"excerpt":"Conformational polymorphism occurs when a compound crystallises in two polymorphs differing only in the relative orientations of flexible groups (e.g. Ritonavir). At the Beilstein conference, Ian Bruno mentioned another type; \u00a0tautomeric polymorphism, where a compound can crystallise in two forms differing in the position of acidic protons. Here I explore\u2026","rel":"","context":"In &quot;Chemical IT&quot;","block_context":{"text":"Chemical IT","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=2"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/06\/109-1024x537.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":16320,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=16320","url_meta":{"origin":16228,"position":4},"title":"Autoionization of hydrogen fluoride.","author":"Henry Rzepa","date":"April 24, 2016","format":false,"excerpt":"The autoionization of water involves two molecules transfering a proton to give hydronium hydroxide, a process for which the free energy of reaction is well known. Here I ask what might happen with the next element along in the periodic table, F. I have been unable to find much about\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":16118,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=16118","url_meta":{"origin":16228,"position":5},"title":"Hydronium hydroxide: the why of pH 7.","author":"Henry Rzepa","date":"April 14, 2016","format":false,"excerpt":"Ammonium hydroxide (NH4+...OH-) can be characterised quantum mechanically when stabilised by water bridges connecting the ion-pairs. It is a small step from there to hydronium hydroxide, or H3O+...OH-. The measured concentrations [H3O+] \u2261 [OH-]\u00a0give\u00a0rise of course to the well-known\u00a0pH 7 of pure water, and converting this ionization constant to a\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":[]}],"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\/16228","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=16228"}],"version-history":[{"count":23,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/16228\/revisions"}],"predecessor-version":[{"id":16302,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/16228\/revisions\/16302"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=16228"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=16228"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=16228"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=16228"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}