{"id":19279,"date":"2017-12-23T19:09:07","date_gmt":"2017-12-23T19:09:07","guid":{"rendered":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=19279"},"modified":"2018-02-25T08:46:10","modified_gmt":"2018-02-25T08:46:10","slug":"can-any-hypervalence-in-diazomethanes-be-amplified","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=19279","title":{"rendered":"Can any hypervalence in diazomethanes be amplified?"},"content":{"rendered":"<div class=\"kcite-section\" kcite-section-id=\"19279\">\n<p>In the <a href=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=19251\">previous post<\/a>, I referred to a recently published review on hypervalency<span id=\"cite_ITEM-19279-0\" name=\"citation\"><a href=\"#ITEM-19279-0\">[1]<\/a><\/span> 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 with cyano and nitro groups.<sup>\u2021<\/sup><\/p>\n<p><img decoding=\"async\" class=\"aligncenter size-large wp-image-19293\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/dicyanodiazomethane-1.svg\" alt=\"\" width=\"450\" \/><\/p>\n<p>Firstly, dicyanodiazomethane. NBO analysis reveals the following atom bond indices;\u00a0C, 3.810; N 3.834; N 2.971. Compare these values to diazomethane itself,\u00a0C, 3.716; N 3.802; N 2.907 and you can see that the carbon bond index has increased slightly. The\u00a0ELF basin integrations (below) which also take into account the &#8220;lone pair&#8221; on carbon are: C, <strong>8.55<\/strong>, N, 6.65, N, 7.52 (DFT), again compared with diazomethane as\u00a0C, <strong>8.16<\/strong>; N, 6.59; N, 7.52. The CASSCF(14,14) result is very similar.<\/p>\n<p><img decoding=\"async\" class=\"aligncenter size-large wp-image-19289\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/dicyanodiazomethane_ELF-2-1024x962.jpg\" alt=\"\" width=\"400\" srcset=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/dicyanodiazomethane_ELF-2-1024x962.jpg 1024w, https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/dicyanodiazomethane_ELF-2-300x282.jpg 300w, https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/dicyanodiazomethane_ELF-2-768x722.jpg 768w, https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/dicyanodiazomethane_ELF-2.jpg 1817w\" sizes=\"(max-width: 1024px) 100vw, 1024px\" \/><\/p>\n<p><img decoding=\"async\" class=\"aligncenter size-large wp-image-19288\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/dicyanodiazomethane_CAS_ELF-1024x632.jpg\" alt=\"\" width=\"400\" srcset=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/dicyanodiazomethane_CAS_ELF-1024x632.jpg 1024w, https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/dicyanodiazomethane_CAS_ELF-300x185.jpg 300w, https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/dicyanodiazomethane_CAS_ELF-768x474.jpg 768w, https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/dicyanodiazomethane_CAS_ELF.jpg 1874w\" sizes=\"(max-width: 1024px) 100vw, 1024px\" \/><\/p>\n<p>So the<strong>\u00a0&#8220;<\/strong>\u03b3(C)&#8221;<sup>\u2020<\/sup> has increased from 8.2 to 8.55. Next, dinitrodiazomethane;<\/p>\n<p><img decoding=\"async\" class=\"aligncenter size-large wp-image-19294\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/dinitrodiazomethane1-1.svg\" alt=\"\" width=\"400\" \/><\/p>\n<p>The NBO bond indices are C, 3.8203; N 3.8255; N 2.9802 and ELF integrations C, <strong>8.82<\/strong>, N, 6.68, N, 7.49 (DFT).<\/p>\n<p><img decoding=\"async\" class=\"aligncenter size-large wp-image-19283\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/dinitrodiazomethane_ELF-1-947x1024.jpg\" alt=\"\" width=\"400\" srcset=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/dinitrodiazomethane_ELF-1-947x1024.jpg 947w, https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/dinitrodiazomethane_ELF-1-278x300.jpg 278w, https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/dinitrodiazomethane_ELF-1-768x830.jpg 768w, https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/12\/dinitrodiazomethane_ELF-1.jpg 1702w\" sizes=\"(max-width: 947px) 100vw, 947px\" \/><\/p>\n<p>So &#8220;\u03b3(C)&#8221;<sup>\u2020<\/sup> \u00a0increases along the series 8.16\u00a0\u2192 8.55\u00a0\u2192 8.82, whereas &#8220;\u03b3(N)&#8221; changes as 6.59\u00a0\u2192 6.65 \u2192 6.68, a smaller effect. Whilst 8.82 is still some way off the value of \u03b3(N)=10 quoted<span id=\"cite_ITEM-19279-0\" name=\"citation\"><a href=\"#ITEM-19279-0\">[1]<\/a><\/span> for diazomethane, dinitrodiazomethane is still a pretty good candidate for hypervalent carbon. The question now is whether even larger values of &#8220;\u03b3(C)&#8221; can be identified in other molecules.\u00a0<\/p>\n<hr \/>\n<p><sup>\u2021<\/sup>FAIR data for all calculations is available at DOI:\u00a0<a href=\"https:\/\/doi.org\/10.14469\/hpc\/3476\">10.14469\/hpc\/3476<\/a>. <sup>\u2020<\/sup>The quotes in &#8220;\u03b3(C)&#8221; indicate it is calculated here using ELF integrations rather than charge maps.<\/p>\n<h2>References<\/h2>\n    <ol class=\"kcite-bibliography csl-bib-body\"><li id=\"ITEM-19279-0\">M.C. Durrant, \"A quantitative definition of hypervalency\", <i>Chemical Science<\/i>, vol. 6, pp. 6614-6623, 2015. <a href=\"https:\/\/doi.org\/10.1039\/c5sc02076j\">https:\/\/doi.org\/10.1039\/c5sc02076j<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> <!-- kcite-section 19279 -->","protected":false},"excerpt":{"rendered":"<p>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 with cyano and nitro groups.\u2021 [&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":[7,4],"tags":[2374,557,1679,1630],"ppma_author":[2661],"class_list":["post-19279","post","type-post","status-publish","format-standard","hentry","category-hypervalency","category-interesting-chemistry","tag-candidate-for-hypervalent-carbon","tag-chemical-bonding","tag-hypervalent-molecule","tag-molecular-geometry"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.5 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Can any hypervalence in diazomethanes be amplified? - 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=19279\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Can any hypervalence in diazomethanes be amplified? - Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"og:description\" content=\"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. 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An attempt into more insight by more &#8220;tuning&#8221; with substituents.","author":"Henry Rzepa","date":"December 26, 2017","format":false,"excerpt":"Recollect the suggestion\u00a0that diazomethane has hypervalent character. When I looked into this, I came to the conclusion that it probably was mildly hypervalent, but on carbon and not nitrogen. Here I try some variations with substituents to see what light if any this casts. I have expanded the resonance forms\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\/2017\/12\/H2CNCCN_ELF-1024x258.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":19251,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=19251","url_meta":{"origin":19279,"position":1},"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":[]},{"id":15823,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=15823","url_meta":{"origin":19279,"position":2},"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":18975,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=18975","url_meta":{"origin":19279,"position":3},"title":"Hypervalence revisited. The odd case of hexamethyl selenium.","author":"Henry Rzepa","date":"November 7, 2017","format":false,"excerpt":"One thread that runs through this blog is that of hypervalency. It was therefore nice to come across a recent review of the concept which revisits the topic, and where a helpful summary is given of the evolving meanings over time of the term hypervalent. The key phrase \"it soon\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\/2017\/11\/165-1024x1008.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":19279,"position":4},"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":19279,"position":5},"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":[]}],"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\/19279","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=19279"}],"version-history":[{"count":14,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/19279\/revisions"}],"predecessor-version":[{"id":19305,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/19279\/revisions\/19305"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=19279"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=19279"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=19279"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=19279"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}