{"id":27870,"date":"2024-10-03T17:50:25","date_gmt":"2024-10-03T16:50:25","guid":{"rendered":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=27870"},"modified":"2025-08-21T14:01:48","modified_gmt":"2025-08-21T13:01:48","slug":"the-one-electron-carbon-carbon-bond-hexafluoroethane-and-ethane-radical-cations","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=27870","title":{"rendered":"The one-electron  carbon-carbon bond: Hexafluoroethane and ethane radical cations."},"content":{"rendered":"<div class=\"kcite-section\" kcite-section-id=\"27870\">\n<p>In the previous post, I looked<span id=\"cite_ITEM-27870-0\" name=\"citation\"><a href=\"#ITEM-27870-0\">[1]<\/a><\/span> at the recently reported<span id=\"cite_ITEM-27870-1\" name=\"citation\"><a href=\"#ITEM-27870-1\">[2]<\/a><\/span> hexa-arylethane containing a carbon-carbon one-electron bond, its structure having been determined by x-ray diffraction (XRD). The measured C-C bond length was ~2.9a\u00c5 and my conclusion was that the C&#8230;C region represented more of a weak &#8220;interaction&#8221; than of a bond as such.\u00a0How about a much simpler system, hexafluoroethane? Here, the two-electron C-F bonds are much lower in energy than the C-C bond, so when the molecule is ionised, it escapes from the\u00a0C-C bond rather than any of the\u00a0C-F bonds. The below is the structure computed at the \u03c9B97XD\/Def2-TZVPP level, revealing a much shorter C-C bond of 2.149\u00c5. The computed C-C stretching vibrational frequency is 179 cm<sup>-1<\/sup> (FAIR data DOI: <span id=\"cite_ITEM-27870-2\" name=\"citation\"><a href=\"#ITEM-27870-2\">[3]<\/a><\/span>)<\/p>\n<p><img decoding=\"async\" onclick=\"jmolApplet([540,540],'load wp-content\/uploads\/2024\/10\/C2F6-radical-cation.log;frame 10;zoom 100;measure 1 2;spin 1;','c2');\" class=\"aligncenter size-full wp-image-27879\" src=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2024\/10\/C2F6-radical-cation.jpg\" alt=\"\" width=\"500\" \/><\/p>\n<p>An electron density\u00a0difference map, obtained by subtracting the computed density of the dication from that of the radical cation at the geometry of the former is shown below, confirming that the electron has been removed from the\u00a0C-C region, with a smaller removal from the\u00a0C-F bonds.<\/p>\n<p><img decoding=\"async\" onclick=\"jmolApplet([540,540],'load wp-content\/uploads\/2024\/10\/C2F6-dication_sub.xyz;isosurface wp-content\/uploads\/2024\/10\/C2F6-dication_sub.jvxl;zoom 140;measure 1 2;spin 1;','c1');\" class=\"aligncenter size-full wp-image-27872\" src=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2024\/10\/C2F6-dication_sub.jpg\" alt=\"\" width=\"500\" \/><\/p>\n<p>The Laplacian of the electron density is shown below contoured for negative values of this function.\u00a0Unlike the previous molecule, this now has a (small) negative value along the C-C region (contour -0.001).<\/p>\n<p><img decoding=\"async\" onclick=\"jmolApplet([540,540],'load wp-content\/uploads\/2024\/10\/C2F6-radical-cation_lap.xyz;isosurface wp-content\/uploads\/2024\/10\/C2F6-radical-cation_lap.jvxl;zoom 150;measure 1 2;spin 1;','c3');\" class=\"aligncenter size-full wp-image-27873\" src=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2024\/10\/C2F6-radical-cation_lap.jpg\" alt=\"\" width=\"500\" \/><\/p>\n<p>A calculation of the\u00a0NCI surface gave a null result! The parameters for computing a non-covalent analysis are thus: <strong>[0.5 1 0.0005 0.05 0.95 1.00]<\/strong>, being the ones used in the previous analysis. The value of <strong>0.05<\/strong> is the density cutoff used to remove covalent density and using this value, no non-covalent features are detected.\u00a0Or, put another way, only covalent features are present, as supported by the -ve Laplacian noted above.<\/p>\n<p>Whilst\u00a0C<sub>2<\/sub>F<sub>6<\/sub><sup>+.<\/sup> cannot be claimed to be typical of a molecule with a hypothetical &#8220;pure&#8221; one-electron C-C bond, it is certainly very different from the previous example.<span id=\"cite_ITEM-27870-0\" name=\"citation\"><a href=\"#ITEM-27870-0\">[1]<\/a><\/span>,<span id=\"cite_ITEM-27870-1\" name=\"citation\"><a href=\"#ITEM-27870-1\">[2]<\/a><\/span> Time to go all the way and try ethane itself, C<sub>2<\/sub>H<sub>6<\/sub><sup>+.<\/sup>. Again the same behavour is seen, whilst the calculated C-C length reduces to 1.933\u00c5. The C-C stretching vibrational frequency is elevated to 477 cm<sup>-1<\/sup>. We might take these last values as the natural ones for a one-electron C-C bond?<\/p>\n<p><img decoding=\"async\" onclick=\"jmolApplet([540,540],'load wp-content\/uploads\/2024\/10\/C2H6-radical-cation.log;frame 18;zoom 150;measure 1 2;spin 1;','c4');\" class=\"aligncenter size-full wp-image-27890\" src=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2024\/10\/ethane-radical-cation.jpg\" alt=\"\" width=\"500\" \/><\/p>\n<p><img decoding=\"async\" onclick=\"jmolApplet([540,540],'load wp-content\/uploads\/2024\/10\/C2H6-dication_sub.xyz;isosurface wp-content\/uploads\/2024\/10\/C2H6-dication_sub.jvxl;zoom 130;measure 1 2;spin 1;','c5');\" class=\"aligncenter size-full wp-image-27887\" src=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2024\/10\/C2H6-dication_sub.jpg\" alt=\"\" width=\"500\" \/><\/p>\n<p>This alternative subtraction involves the density difference between neutral ethane and its radical cation. The result is essentially the same.<\/p>\n<p><img decoding=\"async\" onclick=\"jmolApplet([540,540],'load wp-content\/uploads\/2024\/10\/C2H6-neutral_sub.xyz;isosurface wp-content\/uploads\/2024\/10\/C2H6-neutral_sub.jvxl;zoom 130;measure 1 2;spin 1;','c7');\" class=\"aligncenter size-full wp-image-27887\" src=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2024\/10\/C2H6-neutral_sub.jpg\" alt=\"\" width=\"500\" \/> <\/p>\n<p><img decoding=\"async\" onclick=\"jmolApplet([540,540],'load wp-content\/uploads\/2024\/10\/C2H6-dication_sub.xyz;isosurface wp-content\/uploads\/2024\/10\/C2H6-radical-cation_lap.jvxl;zoom 150;measure 1 2;spin 1;','c6');\" class=\"aligncenter size-full wp-image-27888\" src=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2024\/10\/C2H6-radical-cation_lap.jpg\" alt=\"\" width=\"500\" \/><\/p>\n<p>So these two ethane derivatives add some further context to the properties of a one-electron C-C bond. We have seen them range from a low of ~1.9&Aring; to a high of ~2.9&Aring; This variation of around 1&Aring; as a function of the substituents on the two carbons must be the largest ever seen for any kind of bond!<\/p>\n<h2>References<\/h2>\n    <ol class=\"kcite-bibliography csl-bib-body\"><li id=\"ITEM-27870-0\">H. Rzepa, \"A carbon-carbon one-electron bond! Or a weak carbon-carbon interaction?\", 2024. <a href=\"https:\/\/doi.org\/10.59350\/xp5a3-zsa24\">https:\/\/doi.org\/10.59350\/xp5a3-zsa24<\/a>\n\n<\/li>\n<li id=\"ITEM-27870-1\">G.N. Lewis, \"THE ATOM AND THE MOLECULE.\", <i>Journal of the American Chemical Society<\/i>, vol. 38, pp. 762-785, 1916. <a href=\"https:\/\/doi.org\/10.1021\/ja02261a002\">https:\/\/doi.org\/10.1021\/ja02261a002<\/a>\n\n<\/li>\n<li id=\"ITEM-27870-2\">H. Rzepa, \"A carbon-carbon one-electron bond! Or a weak carbon-carbon interaction?\", 2024. <a href=\"https:\/\/doi.org\/10.14469\/hpc\/14642\">https:\/\/doi.org\/10.14469\/hpc\/14642<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> <!-- kcite-section 27870 -->","protected":false},"excerpt":{"rendered":"<p>In the previous post, I looked at the recently reported hexa-arylethane containing a carbon-carbon one-electron bond, its structure having been determined by x-ray diffraction (XRD). The measured C-C bond length was ~2.9a\u00c5 and my conclusion was that the C&#8230;C region represented more of a weak &#8220;interaction&#8221; than of a bond as such.\u00a0How about a much [&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":[],"ppma_author":[2661],"class_list":["post-27870","post","type-post","status-publish","format-standard","hentry","category-interesting-chemistry"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.5 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>The one-electron carbon-carbon bond: Hexafluoroethane and ethane radical cations. - 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=27870\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"The one-electron carbon-carbon bond: Hexafluoroethane and ethane radical cations. - Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"og:description\" content=\"In the previous post, I looked at the recently reported hexa-arylethane containing a carbon-carbon one-electron bond, its structure having been determined by x-ray diffraction (XRD). The measured C-C bond length was ~2.9a\u00c5 and my conclusion was that the C&#8230;C region represented more of a weak &#8220;interaction&#8221; than of a bond as such.\u00a0How about a much [&hellip;]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=27870\" \/>\n<meta property=\"og:site_name\" content=\"Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"article:published_time\" content=\"2024-10-03T16:50:25+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2025-08-21T13:01:48+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=\"4 minutes\" \/>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"The one-electron carbon-carbon bond: Hexafluoroethane and ethane radical cations. - 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=27870","og_locale":"en_GB","og_type":"article","og_title":"The one-electron carbon-carbon bond: Hexafluoroethane and ethane radical cations. - Henry Rzepa&#039;s Blog","og_description":"In the previous post, I looked at the recently reported hexa-arylethane containing a carbon-carbon one-electron bond, its structure having been determined by x-ray diffraction (XRD). The measured C-C bond length was ~2.9a\u00c5 and my conclusion was that the C&#8230;C region represented more of a weak &#8220;interaction&#8221; than of a bond as such.\u00a0How about a much [&hellip;]","og_url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=27870","og_site_name":"Henry Rzepa&#039;s Blog","article_published_time":"2024-10-03T16:50:25+00:00","article_modified_time":"2025-08-21T13:01:48+00:00","author":"Henry Rzepa","twitter_card":"summary_large_image","twitter_misc":{"Written by":"Henry Rzepa","Estimated reading time":"4 minutes"},"schema":{"@context":"https:\/\/schema.org","@graph":[{"@type":"Article","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=27870#article","isPartOf":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=27870"},"author":{"name":"Henry Rzepa","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/#\/schema\/person\/2b40f7b9c872a4dc1547e040a11b6281"},"headline":"The one-electron carbon-carbon bond: Hexafluoroethane and ethane radical cations.","datePublished":"2024-10-03T16:50:25+00:00","dateModified":"2025-08-21T13:01:48+00:00","mainEntityOfPage":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=27870"},"wordCount":455,"commentCount":6,"image":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=27870#primaryimage"},"thumbnailUrl":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2024\/10\/C2F6-radical-cation.jpg","articleSection":["Interesting chemistry"],"inLanguage":"en-GB","potentialAction":[{"@type":"CommentAction","name":"Comment","target":["https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=27870#respond"]}]},{"@type":"WebPage","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=27870","url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=27870","name":"The one-electron carbon-carbon bond: Hexafluoroethane and ethane radical cations. - 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=27870#primaryimage"},"image":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=27870#primaryimage"},"thumbnailUrl":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2024\/10\/C2F6-radical-cation.jpg","datePublished":"2024-10-03T16:50:25+00:00","dateModified":"2025-08-21T13:01:48+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=27870#breadcrumb"},"inLanguage":"en-GB","potentialAction":[{"@type":"ReadAction","target":["https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=27870"]}]},{"@type":"ImageObject","inLanguage":"en-GB","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=27870#primaryimage","url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2024\/10\/C2F6-radical-cation.jpg","contentUrl":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2024\/10\/C2F6-radical-cation.jpg","width":2578,"height":1810},{"@type":"BreadcrumbList","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=27870#breadcrumb","itemListElement":[{"@type":"ListItem","position":1,"name":"Home","item":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog"},{"@type":"ListItem","position":2,"name":"The one-electron carbon-carbon bond: Hexafluoroethane and ethane radical cations."}]},{"@type":"WebSite","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/#website","url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/","name":"Henry Rzepa&#039;s Blog","description":"Chemistry with a twist","potentialAction":[{"@type":"SearchAction","target":{"@type":"EntryPoint","urlTemplate":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?s={search_term_string}"},"query-input":{"@type":"PropertyValueSpecification","valueRequired":true,"valueName":"search_term_string"}}],"inLanguage":"en-GB"},{"@type":"Person","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/#\/schema\/person\/2b40f7b9c872a4dc1547e040a11b6281","name":"Henry Rzepa","image":{"@type":"ImageObject","inLanguage":"en-GB","@id":"https:\/\/secure.gravatar.com\/avatar\/897b6740f7f599bca7942cdf7d7914af5988937ae0e3869ab09aebb87f26a731?s=96&d=blank&r=g370be3a7397865e4fd161aefeb0a5a85","url":"https:\/\/secure.gravatar.com\/avatar\/897b6740f7f599bca7942cdf7d7914af5988937ae0e3869ab09aebb87f26a731?s=96&d=blank&r=g","contentUrl":"https:\/\/secure.gravatar.com\/avatar\/897b6740f7f599bca7942cdf7d7914af5988937ae0e3869ab09aebb87f26a731?s=96&d=blank&r=g","caption":"Henry Rzepa"},"description":"Henry Rzepa is Emeritus Professor of Computational Chemistry at Imperial College London.","sameAs":["https:\/\/orcid.org\/0000-0002-8635-8390"],"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?author=1"}]}},"jetpack_publicize_connections":[],"jetpack_featured_media_url":"","jetpack_sharing_enabled":true,"jetpack_shortlink":"https:\/\/wp.me\/pDef7-7fw","jetpack-related-posts":[{"id":27788,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=27788","url_meta":{"origin":27870,"position":0},"title":"A carbon-carbon one-electron bond!  Or a weak carbon-carbon interaction?","author":"Henry Rzepa","date":"October 1, 2024","format":false,"excerpt":"More than 100 years ago, before the quantum mechanical treatment of molecules had been formulated, G. N. Lewis proposed a simple model for chemical bonding that is still taught today. This is the idea of the three categories of bond we know as single, double and triple, comprising respectively two,\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":27944,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=27944","url_meta":{"origin":27870,"position":1},"title":"A one-electron bond in methyl-\u03bb1-borane.","author":"Henry Rzepa","date":"October 9, 2024","format":false,"excerpt":"In exploring one-electron carbon-carbon bonds, I had noted previously that both hexafluoroethane and ethane itself could each lose an electron to produce such species. A discussion developed in which a molecule isoelectronic with ethane radical cation, namely the methyl-\u03bb1-borane radical (H3B-CH3) was proposed by Jacob. The optimised structure at the\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":17829,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=17829","url_meta":{"origin":27870,"position":2},"title":"First, hexacoordinate carbon &#8211; now pentacoordinate nitrogen?","author":"Henry Rzepa","date":"March 25, 2017","format":false,"excerpt":"A few years back I followed a train of thought here which ended with hexacoordinate carbon, then a hypothesis rather than a demonstrated reality. That reality was recently confirmed via a crystal structure,\u00a0DOI:10.5517\/CCDC.CSD.CC1M71QM. Here is a\u00a0similar proposal for\u00a0penta-coordinate nitrogen. First, a search of the CSD (Cambridge structure database) for such\u00a0nitrogen.\u2026","rel":"","context":"In &quot;Bond slam&quot;","block_context":{"text":"Bond slam","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=2237"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]},{"id":17122,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=17122","url_meta":{"origin":27870,"position":3},"title":"Long C=C bonds.","author":"Henry Rzepa","date":"December 1, 2016","format":false,"excerpt":"Following on from a search for long C-C bonds, here is the same repeated for C=C double bonds. The query restricts the search to each carbon having just two non-metallic substituents. To avoid conjugation with these, they each are 4-coordinated; the carbons themselves are three-coordinated. Further constraints are the usual\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":"sq","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/12\/sq-1024x415.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":25581,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=25581","url_meta":{"origin":27870,"position":4},"title":"Examples of inverted or hemispherical carbon?","author":"Henry Rzepa","date":"September 15, 2022","format":false,"excerpt":"In previously asking what the largest angle subtended at four-coordinate carbon might be, I noted that as the angle increases beyond 180\u00b0, the carbon becomes inverted, or hemispherical (all four ligands in one hemisphere). So what does a search for this situation reveal in the CSD? The query can be\u2026","rel":"","context":"With 2 comments","block_context":{"text":"With 2 comments","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=25581#comments"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2022\/09\/111-nbo.jpg?resize=350%2C200&ssl=1","width":350,"height":200,"srcset":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2022\/09\/111-nbo.jpg?resize=350%2C200&ssl=1 1x, https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2022\/09\/111-nbo.jpg?resize=525%2C300&ssl=1 1.5x, https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2022\/09\/111-nbo.jpg?resize=700%2C400&ssl=1 2x"},"classes":[]},{"id":19251,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=19251","url_meta":{"origin":27870,"position":5},"title":"Are diazomethanes hypervalent molecules? Probably, but in an unexpected way!","author":"Henry Rzepa","date":"December 23, 2017","format":false,"excerpt":"A recently published review on hypervalency introduced a very simple way of quantifying the effect. One of the molecules which was suggested to be hypervalent using this method was diazomethane. Here I take a closer look. The new method is called the valence electron equivalent \u03b3. It is defined as\u00a0\"the\u2026","rel":"","context":"In &quot;Hypervalency&quot;","block_context":{"text":"Hypervalency","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=7"},"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\/27870","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=27870"}],"version-history":[{"count":40,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/27870\/revisions"}],"predecessor-version":[{"id":27932,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/27870\/revisions\/27932"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=27870"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=27870"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=27870"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=27870"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}