{"id":2687,"date":"2010-10-23T21:50:50","date_gmt":"2010-10-23T20:50:50","guid":{"rendered":"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=2687"},"modified":"2012-07-26T08:06:20","modified_gmt":"2012-07-26T07:06:20","slug":"hypervalency-third-time-lucky","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=2687","title":{"rendered":"Hypervalency:  Third time lucky?"},"content":{"rendered":"<div class=\"kcite-section\" kcite-section-id=\"2687\">\n<p>One approach to reporting science which is perhaps better suited to the medium of a blog than a conventional journal article is the opportunity to follow ideas in unexpected, even unconventional directions. Thus my third attempt, like a dog worrying a bone, to explore hypervalency. I have, somewhat to my surprise, found myself contemplating the two molecules I<sub>8<\/sub> and At<sub>8<\/sub>. Perhaps it might be better to write them as I(I)<sub>7<\/sub> and At(At)<sub>7<\/sub>. This makes it easier to relate both to the known molecule I(F)<sub>7<\/sub>. What led to these (allotropes) of the halogens? Well, as I noted before, hypervalency is a concept rooted in covalency, albeit an excess of it! And bonds with the same atom at each end are less likely to be accused of ionicity. I earlier suggested that the nicely covalent IH<sub>7<\/sub> was not hypervalent, with all the electrons which might contribute to hypervalency actually to be found in the H&#8230;H regions. The next candidate, I(CN)<sub>7<\/sub> ultimately proved a little too ionic for comfort. So we arrive at II<sub>7<\/sub>. At the D<sub>5h<\/sub> geometry, it proves not to be a minimum, but a (degenerate) transition state for reductive elimination of I<sub>2<\/sub> (I note parabolically that the <a href=\"http:\/\/nobelprize.org\/nobel_prizes\/chemistry\/laureates\/2010\/\" target=\"_blank\">2010 Nobel prize for chemistry<\/a> was awarded for reactions which involve similar reductive elimination of Pd and other metals to form covalent C-C bonds). Thus I<sub>8<\/sub> is useful only as a thought experiment molecule, and not a species that could actually be made.<\/p>\n<div id=\"attachment_2690\" style=\"width: 288px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-2690\" class=\"size-full wp-image-2690\" title=\"I8\" onclick=\"jmolInitialize('..\/Jmol\/');jmolSetAppletColor('red');jmolApplet([600,600],'load wp-content\/uploads\/2010\/10\/I8.log;frame 23;set measurementUnits Angstroms;delay 5;vectors on;vectors 4;vectors scale 5.0; color vectors purple; vibration 15;animation mode loop;');\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2010\/10\/I8.jpg\" alt=\"\" width=\"278\" height=\"257\" \/><p id=\"caption-attachment-2690\" class=\"wp-caption-text\">I8, showing as a transition state for reductive elimination of iodine. Click for 3D<\/p><\/div>\n<p>The <a href=\"http:\/\/hdl.handle.net\/10042\/to-5238\" target=\"_blank\">Wiberg bond index<\/a>\u00a0(B3LYP\/Def2-TZVPP basis+pseudopotential)\u00a0of the central iodine comes out at 2.81; that of the two axial iodines is 1.05 and that of the five equatorial atoms is 1.50. Well, the axial iodines are clearly monovalent, the equatorial ones are higher because of I&#8230;I interactions around the 5-ring. The central iodine is clearly again, not hypervalent. The individual Wiberg bond orders radiating form the central atom are 0.47 for the axial and 0.374 for the equatorial atoms. The I&#8230;I bond orders between the five equatorial atoms are 0.336 for adjacent atoms. This latter observation matches with the frequency analysis, since any individual I-I bond is already 1\/3 formed, just asking to be eliminated.<\/p>\n<p>What of that other technique for finding electrons, ELF?<\/p>\n<div id=\"attachment_2691\" style=\"width: 286px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-2691\" class=\"size-full wp-image-2691\" title=\"I8-elf\" onclick=\"jmolInitialize('..\/Jmol\/');jmolSetAppletColor('green');jmolApplet([600,600],'load wp-content\/uploads\/2010\/10\/I8-elf.mol;');\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2010\/10\/I8-elf.jpg\" alt=\"\" width=\"276\" height=\"283\" \/><p id=\"caption-attachment-2691\" class=\"wp-caption-text\">ELF analysis for I8. Click for 3D<\/p><\/div>\n<p>All the I-I bonds radiating from the centre have well-defined disynaptic basins (the same is NOT true for e.g. IF<sub>7<\/sub>by the way, which comes out as ionic in ELF). The two axial covalent bonds have basins integrating to 1.35 electrons, and the five equatorial covalent bonds 0.77. The central iodine has a total of 6.55 electrons in bonds surrounding it. The five equatorial iodines have 7.7 electrons in two lone pairs, whilst the two axial iodines have 8.05 electrons in five monosynaptic basins. In summary, all eight iodines in this compound exhibit valence shells filled with an octet of electrons. Now, beyond any ambiguity, we can say this is NOT hypervalent.<\/p>\n<p>Oh, for good measure, <a href=\"http:\/\/hdl.handle.net\/10042\/to-5264\" target=\"_blank\">At8<\/a>. The Wiberg index at the central atom is 2.77, the bond index is 0.46 for axial and 0.37 for equatorial At. The ELF basin integrations are 0.65 for equatorial, and 1.61 for axial, the former decreasing and the latter increasing compared to iodine.<\/p>\n<div id=\"attachment_2692\" style=\"width: 299px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-2692\" class=\"size-full wp-image-2692\" title=\"At8-elf\" onclick=\"jmolInitialize('..\/Jmol\/');jmolSetAppletColor('green');jmolApplet([600,600],'load wp-content\/uploads\/2010\/10\/At8-elf.mol;');\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2010\/10\/At8-elf.jpg\" alt=\"\" width=\"289\" height=\"289\" \/><p id=\"caption-attachment-2692\" class=\"wp-caption-text\">ELF analysis for At8. Click for 3D.<\/p><\/div>\n<!-- kcite active, but no citations found -->\n<\/div> <!-- kcite-section 2687 -->","protected":false},"excerpt":{"rendered":"<p>One approach to reporting science which is perhaps better suited to the medium of a blog than a conventional journal article is the opportunity to follow ideas in unexpected, even unconventional directions. Thus my third attempt, like a dog worrying a bone, to explore hypervalency. I have, somewhat to my surprise, found myself contemplating the [&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":"","footnotes":"","jetpack_publicize_message":"","jetpack_publicize_feature_enabled":true,"jetpack_social_post_already_shared":false,"jetpack_social_options":{"image_generator_settings":{"template":"highway","default_image_id":0,"font":"","enabled":false},"version":2},"jetpack_post_was_ever_published":false},"categories":[7],"tags":[2649,302],"ppma_author":[2661],"class_list":["post-2687","post","type-post","status-publish","format-standard","hentry","category-hypervalency","tag-hypervalency","tag-wiberg"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Hypervalency: Third time lucky? - 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=2687\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Hypervalency: Third time lucky? - Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"og:description\" content=\"One approach to reporting science which is perhaps better suited to the medium of a blog than a conventional journal article is the opportunity to follow ideas in unexpected, even unconventional directions. 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The latter is defined not so much by expanding the total valence shell of electrons surrounding the hypervalent\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":"YOCVIV: Crystal structure of hexacoordinate boron","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/10\/BBr.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":2619,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=2619","url_meta":{"origin":2687,"position":1},"title":"Hypervalency: I(CN)7 is not hypervalent!","author":"Henry Rzepa","date":"October 17, 2010","format":false,"excerpt":"In the last post, IH7 was examined to see if it might exhibit true hypervalency. The iodine, despite its high coordination, turned out not to be hypervalent, with its (s\/p) valence shell not exceeding eight electrons (and its d-shell still with 10, and the 6s\/6p shells largely unoccupied). Instead, 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":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2010\/10\/ICN7.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":2599,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=2599","url_meta":{"origin":2687,"position":2},"title":"Hypervalency: Is it real?","author":"Henry Rzepa","date":"October 16, 2010","format":false,"excerpt":"The Wikipedia page on hypervalent compounds reveals that the concept is almost as old as that of normally valent compounds. The definition there, \u00a0is \"a molecule that contains one or more\u00a0main group elements formally bearing more than eight\u00a0electrons in their\u00a0valence shells\" (although it could equally apply to e.g. transition elements\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":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2010\/10\/IH7.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":19499,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=19499","url_meta":{"origin":2687,"position":3},"title":"Never mind main group &#8220;hypervalency&#8221;, what about transition metal &#8220;hypervalency&#8221;?","author":"Henry Rzepa","date":"March 18, 2018","format":false,"excerpt":"I have posted often on the chemical phenomenon known as hypervalency, being careful to state that as defined it applies just to \"octet excess\" in main group elements. But what about the next valence shell, occurring in transition metals and known as the \"18-electron rule\"? You rarely hear the term\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":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2018\/03\/NiPP-987x1024.jpg?resize=350%2C200&ssl=1","width":350,"height":200},"classes":[]},{"id":19279,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=19279","url_meta":{"origin":2687,"position":4},"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":[]},{"id":936,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=936","url_meta":{"origin":2687,"position":5},"title":"Full circle with carbon hypervalencies","author":"Henry Rzepa","date":"October 2, 2009","format":false,"excerpt":"The previous post talked about making links or connections. And part of the purpose for presenting this chemistry as a blog is to expose how these connections are made, or or less as it happens in real time (and\u00a0not the chronologically sanitized version of discovery that most research papers are).\u00a0So\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":"C4-symmetric pentavalent carbon","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/10\/c4.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","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\/2687","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=2687"}],"version-history":[{"count":2,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/2687\/revisions"}],"predecessor-version":[{"id":7387,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/2687\/revisions\/7387"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=2687"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=2687"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=2687"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=2687"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}