{"id":19194,"date":"2017-12-08T14:48:51","date_gmt":"2017-12-08T14:48:51","guid":{"rendered":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=19194"},"modified":"2017-12-08T21:10:39","modified_gmt":"2017-12-08T21:10:39","slug":"identification-of-a-simplest-hypervalent-hydrogen-fluoride-anion","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=19194","title":{"rendered":"Identification of a simplest hypervalent hydrogen fluoride anion."},"content":{"rendered":"<div class=\"kcite-section\" kcite-section-id=\"19194\">\n<p>An article with the title shown above in part recently appeared.<span id=\"cite_ITEM-19194-0\" name=\"citation\"><a href=\"#ITEM-19194-0\">[1]<\/a><\/span> Given the apparent similarity of HF<sup>1-<\/sup> to CH<sub>3<\/sub>F<sup>1-<\/sup> and CH<sub>3<\/sub>F<sup>2-<\/sup>, the latter of which I <a href=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=15823\">introduced on this blog previously,\u00a0<\/a>I thought it of interest to apply my analysis to HF<sup>1-<\/sup>.<\/p>\n<p>The authors<span id=\"cite_ITEM-19194-0\" name=\"citation\"><a href=\"#ITEM-19194-0\">[1]<\/a><\/span> conclude that &#8220;<em>the F atom of HF<sup>\u2212<\/sup> is negative and hypervalent and the bonding is more covalent than ionic<\/em>&#8220;.\u00a0So, firstly an NBO analysis. Shown below is the singly occupied NBO (\u03c9B97XD\/Def2-TZVPPD calculation, FAIR data DOI: <a href=\"https:\/\/doi.org\/10.14469\/hpc\/3274\">10.14469\/hpc\/3274)<\/a><\/p>\n<p><img decoding=\"async\" class=\"aligncenter size-full wp-image-19196\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/HF-NBO.jpg\" alt=\"\" width=\"300\" srcset=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/HF-NBO.jpg 801w, https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/HF-NBO-300x264.jpg 300w, https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/HF-NBO-768x677.jpg 768w\" sizes=\"(max-width: 801px) 100vw, 801px\" \/><\/p>\n<p>The nature of this orbital is that most of it is located beyond the hydrogen and a node is apparent between the F and H (it is H-F antibonding). The Wiberg bond index for both H and F is 0.48, as is the F-H bond order. This matches with the observation of one electron in an orbital which is H-F antibonding. NBO analysis also indicates that the atomic orbital contributions to F[core]2S(1.93)2p(5.77)3S(<span style=\"color: #ff0000;\">0.05<\/span>)3p(<span style=\"color: #ff0000;\">0.04<\/span>)3d(0.01) and H 1S(0.96)2S(<span style=\"color: #ff0000;\">0.12<\/span>)2p(<span style=\"color: #ff0000;\">0.10<\/span>) show modest Rydberg character on the hydrogen, less on the fluorine. By this criterion, it is the hydrogen and not the fluorine that is hypervalent!<\/p>\n<p>Next, the ELF analysis (respectively FAIR data DOI: DFT\u00a0<a href=\"https:\/\/doi.org\/10.14469\/hpc\/3377\">10.14469\/hpc\/3377<\/a>\u00a0 and CASSCF(7,8)\u00a0<a href=\"https:\/\/doi.org\/10.14469\/hpc\/3394\">10.14469\/hpc\/3394<\/a>).\u00a0<\/p>\n<table border=\"0\">\n<tbody>\n<tr>\n<th>DFT<\/th>\n<th>CASSCF(7,8)<\/th>\n<\/tr>\n<tr>\n<td><img decoding=\"async\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/HF-.jpg\" alt=\"\" width=\"150\" \/><\/td>\n<td><img decoding=\"async\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/HF-CAS.jpg\" alt=\"\" width=\"130\" \/><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p>Both these methods reveal a monosynaptic ELF basin located away from the H, with an integration of about 1 electron. The F lone pairs form a torus around the F and the total of electrons around the fluorine is &lt;8. So again no evidence from ELF that the fluorine is hypervalent.<\/p>\n<p>In fact this analysis resembles one feature of <a href=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=10801\">CLi6<\/a>. With nominally 12e apparently contributing to the shared C-Li shell, CLi<sub>6<\/sub> was described as hypervalent.<span id=\"cite_ITEM-19194-1\" name=\"citation\"><a href=\"#ITEM-19194-1\">[2]<\/a><\/span> In fact ~3e of these are &#8220;expelled&#8221; from the shared C-Li regions into Li-Li regions, where they contribute only to lithium valency and not to the carbon valency. With\u00a0HF<sup>1-<\/sup>, the additional electron apparently responsible for the <i>hypervalency <\/i>contributes only to the H, but <strong>not<\/strong> to the F valencies. With\u00a0CH<sub>3<\/sub>F<sup>2-<\/sup>, the two injected electrons do appear to contribute to the C-F bond, making it a true <strong>hyperbond<\/strong>.<\/p>\n<p>So based on the above, I cannot entirely agree with the assertion that &#8220;<em>the F atom of HF<sup>\u2212<\/sup> is negative and hypervalent&#8221;<\/em><span id=\"cite_ITEM-19194-0\" name=\"citation\"><a href=\"#ITEM-19194-0\">[1]<\/a><\/span>, but I might suggest that something more unusual is happening, the <strong>hydrogen<\/strong> is (mildly) hypervalent!\u00a0<\/p>\n<h2>References<\/h2>\n    <ol class=\"kcite-bibliography csl-bib-body\"><li id=\"ITEM-19194-0\">M. Liu, H. Chen, C. Chin, T. Huang, Y. Chen, and Y. Wu, \"Identification of a Simplest Hypervalent Hydrogen Fluoride Anion in Solid Argon\", <i>Scientific Reports<\/i>, vol. 7, 2017. <a href=\"https:\/\/doi.org\/10.1038\/s41598-017-02687-z\">https:\/\/doi.org\/10.1038\/s41598-017-02687-z<\/a>\n\n<\/li>\n<li id=\"ITEM-19194-1\">H. Kudo, \"Observation of hypervalent CLi6 by Knudsen-effusion mass spectrometry\", <i>Nature<\/i>, vol. 355, pp. 432-434, 1992. <a href=\"https:\/\/doi.org\/10.1038\/355432a0\">https:\/\/doi.org\/10.1038\/355432a0<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> <!-- kcite-section 19194 -->","protected":false},"excerpt":{"rendered":"<p>An article with the title shown above in part recently appeared. Given the apparent similarity of HF1- to CH3F1- and CH3F2-, the latter of which I introduced on this blog previously,\u00a0I thought it of interest to apply my analysis to HF1-. The authors conclude that &#8220;the F atom of HF\u2212 is negative and hypervalent and [&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":[7],"tags":[],"ppma_author":[2661],"class_list":["post-19194","post","type-post","status-publish","format-standard","hentry","category-hypervalency"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.5 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Identification of a simplest hypervalent hydrogen fluoride anion. - 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=19194\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Identification of a simplest hypervalent hydrogen fluoride anion. - Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"og:description\" content=\"An article with the title shown above in part recently appeared. Given the apparent similarity of HF1- to CH3F1- and CH3F2-, the latter of which I introduced on this blog previously,\u00a0I thought it of interest to apply my analysis to HF1-. The authors conclude that &#8220;the F atom of HF\u2212 is negative and hypervalent and [&hellip;]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=19194\" \/>\n<meta property=\"og:site_name\" content=\"Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"article:published_time\" content=\"2017-12-08T14:48:51+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2017-12-08T21:10:39+00:00\" \/>\n<meta property=\"og:image\" content=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/HF-NBO.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=\"2 minutes\" \/>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"Identification of a simplest hypervalent hydrogen fluoride anion. - 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=19194","og_locale":"en_GB","og_type":"article","og_title":"Identification of a simplest hypervalent hydrogen fluoride anion. - Henry Rzepa&#039;s Blog","og_description":"An article with the title shown above in part recently appeared. Given the apparent similarity of HF1- to CH3F1- and CH3F2-, the latter of which I introduced on this blog previously,\u00a0I thought it of interest to apply my analysis to HF1-. 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It was a very rare computed example of a system where the added two electrons populate the higher valence shells known as Rydberg orbitals as an alternative to populating the C-F antibonding \u03c3-orbital to produce CH3- and F-. The net\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":[]},{"id":19383,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=19383","url_meta":{"origin":19194,"position":1},"title":"Hypervalent  Helium &#8211; not!","author":"Henry Rzepa","date":"February 16, 2018","format":false,"excerpt":"Last year, this article attracted a lot of attention as the first example of molecular helium in the form of Na2He. In fact, the helium in this species has a calculated\u2021 bond index of only 0.15 and it is better classified as a sodium electride with the ionisation induced by\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":[]},{"id":10801,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=10801","url_meta":{"origin":19194,"position":2},"title":"Is  CLi6 hypervalent?","author":"Henry Rzepa","date":"July 5, 2013","format":false,"excerpt":"A comment made on the previous post on the topic of hexa-coordinate carbon cited an article entitled \"Observation of hypervalent CLi6\u00a0by Knudsen-effusion mass spectrometry\" by Kudo as a amongst the earliest of evidence that such species can exist (in the gas phase). It was a spectacular vindication of the earlier\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":"Click for  3D","src":"https:\/\/i0.wp.com\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/07\/CLi6-Lp.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":15823,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=15823","url_meta":{"origin":19194,"position":3},"title":"Real hypervalency in a small molecule.","author":"Henry Rzepa","date":"February 21, 2016","format":false,"excerpt":"Hypervalency is defined as a molecule\u00a0that contains one or more main group elements formally bearing more than eight\u00a0 electrons in their\u00a0 valence shell. One example of a molecule so characterised was CLi6 where the description \"\u201ccarbon can expand its octet of electrons to form this relatively stable molecule\u201c was used.\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":"CH4","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/02\/CH4.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":10839,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=10839","url_meta":{"origin":19194,"position":4},"title":"Hexacoordinate hydrogen.","author":"Henry Rzepa","date":"July 8, 2013","format":false,"excerpt":"A feature of a blog which is quite different from a journal article is how rapidly a topic might evolve.\u00a0Thus I started a few days ago with the theme of dicarbon (C2), identifying a metal carbide that showed C2 as a ligand, but which also entrapped a single carbon in\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":"Click for  3D.","src":"https:\/\/i0.wp.com\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/07\/6-H.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":19279,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=19279","url_meta":{"origin":19194,"position":5},"title":"Can any hypervalence in diazomethanes be amplified?","author":"Henry Rzepa","date":"December 23, 2017","format":false,"excerpt":"In the previous post, I referred to a recently published review on hypervalency which introduced a very simple way (the\u00a0valence electron equivalent \u03b3)\u00a0of quantifying the effect.\u00a0Diazomethane was cited as one example of a small molecule exhibiting hypervalency (on nitrogen) by this measure. Here I explore the effect of substituting diazomethane\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\/19194","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=19194"}],"version-history":[{"count":8,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/19194\/revisions"}],"predecessor-version":[{"id":19206,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/19194\/revisions\/19206"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=19194"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=19194"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=19194"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=19194"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}