{"id":1243,"date":"2009-12-05T14:11:14","date_gmt":"2009-12-05T13:11:14","guid":{"rendered":"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1243"},"modified":"2009-12-05T20:23:13","modified_gmt":"2009-12-05T19:23:13","slug":"the-nature-of-the-cs-triple-bond-part-2","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1243","title":{"rendered":"The nature of the C\u2261S Triple bond: Part 2"},"content":{"rendered":"<div class=\"kcite-section\" kcite-section-id=\"1243\">\n<p>In my <a href=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1210\" target=\"_blank\">first post on this theme<\/a>, an ELF (Electron localization function) analysis of the bonding in the molecule HO-S\u2261C-H (DOI: <a href=\"http:\/\/dx.doi.org\/10.1002\/anie.200903969\" target=\"references\">10.1002\/anie.200903969<\/a>) was presented. This analysis identified a lone pair of electrons localized on the carbon (integrating in fact to almost exactly 2.0) in addition to electrons in the CC region. This picture seems to indicate that the triple bond splits into two well defined regions of electron density (synaptic basins). In a comment to this post, I also <a href=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1210&amp;cpage=1#comment-1877\" target=\"_blank\">pointed out<\/a> that an NBO analysis showed a large interaction energy between the carbon lone pair and the S-O \u03c3<sup>*<\/sup> orbital, characteristic of <a href=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=745\" target=\"_blank\">anomeric effects<\/a> (in eg sugars). This latter observation gives us a handle on possibly tweaking the effect. Thus if the S-O \u03c3* orbital can be made a better electron acceptor, then its interaction with the lone pair could be enhanced.<\/p>\n<p>Accordingly, the analysis has been repeated for H-C\u2261S-OTf (OTf = triflate = trifluoromethane sulfonate), since the triflate would be expected to increase significantly the electron accepting properties of the S-O bond.<\/p>\n<p><div id=\"attachment_1244\" style=\"width: 466px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-1244\" class=\"size-full wp-image-1244\" title=\"CSOTf\" onclick=\"jmolInitialize('..\/Jmol\/');jmolSetAppletColor('cyan');jmolApplet([450,450],'load wp-content\/uploads\/2009\/12\/CS-OTF-elf.mol;zoom 120;spin 3;set fontscaling TRUE; font label 14;select atomno=15;label %A 2.56;select atomno=17;label %A 1.86;');\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/12\/CSOTf.jpg\" alt=\"ELF analysis for H-C\u2261S-OTf\" width=\"456\" height=\"279\" \/><p id=\"caption-attachment-1244\" class=\"wp-caption-text\">ELF analysis for H-C\u2261S-OTf. Click for 3D model<\/p><\/div>One dramatic change has indeed occurred. Previously, a well-defined ELF disynaptic basin had been identified in the S-O region, with an integration of 1.12e. If the OH group is replaced by OTf, this disynaptic basin can no longer be located. The electrons have instead moved into sulfur lone pairs, and the S-CF<sub>3<\/sub> bond, which is an expected consequence of the greater electronegativity of the triflate group. Point 15 (the S=C region) integrates to 2.56e (compared with 2.36 for the OH analogue), and the carbon lone pair decreases from 2.01 to 1.86e.<\/p>\n<p>Taken as a whole, these changes suggest that the CS bond has gotten stronger, resulting from transfer of electron density from the non-bonding carbon lone pair, to the CS bond itself. Indeed, its length is now 1.492\u00c5, a significant shrinkage compared to 1.544\u00c5 for the OH parent (B3LYP\/cc-pVTZ). Likewise, the C-S vibrational stretch of 1381 cm<sup>-1<\/sup> for the OTf derivative is an increase over 1215 cm<sup>-1<\/sup> for the OH system and 1304 cm<sup>-1<\/sup> for diatomic CS itself (B3LYP\/cc-pVTZ).<\/p>\n<p>These results suggest that the ELF procedure, combined with the insight from the NBO analysis, can be used as a tool to rationally design a variation to the original molecule which does appear to enhance the triple bond character of the CS region, and to fulfil further the ambition of the <a href=\"http:\/\/dx.doi.org\/10.1002\/anie.200903969\" target=\"_blank\">original article<\/a> by Schreiner and co-workers. As a triflate, it may even be susceptible to a simple preparation from the alcohol parent! Anyone up for it?<\/p>\n<p>It is also worth noting that the above system is headed off towards HC\u2261S<sup>+<\/sup>, the thioacylium cation (although crystal structures of the acylium ion are known, none have been reported for the thioacylium ion). Both N\u2261N and C\u2261O contract their bond lengths when protonated, so it should be no great surprise to find that CS does so as well (1.476\u00c5, \u03bd 1543 cm<sup>-1<\/sup>).<\/p>\n<!-- kcite active, but no citations found -->\n<\/div> <!-- kcite-section 1243 -->","protected":false},"excerpt":{"rendered":"<p>In my first post on this theme, an ELF (Electron localization function) analysis of the bonding in the molecule HO-S\u2261C-H (DOI: 10.1002\/anie.200903969) was presented. This analysis identified a lone pair of electrons localized on the carbon (integrating in fact to almost exactly 2.0) in addition to electrons in the CC region. This picture seems to [&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":false,"jetpack_social_options":{"image_generator_settings":{"template":"highway","default_image_id":0,"font":"","enabled":false},"version":2}},"categories":[7,4],"tags":[2649,2648,162],"ppma_author":[2661],"class_list":["post-1243","post","type-post","status-publish","format-standard","hentry","category-hypervalency","category-interesting-chemistry","tag-hypervalency","tag-interesting-chemistry","tag-large-interaction-energy"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.5 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>The nature of the C\u2261S Triple bond: Part 2 - 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=1243\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"The nature of the C\u2261S Triple bond: Part 2 - Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"og:description\" content=\"In my first post on this theme, an ELF (Electron localization function) analysis of the bonding in the molecule HO-S\u2261C-H (DOI: 10.1002\/anie.200903969) was presented. This analysis identified a lone pair of electrons localized on the carbon (integrating in fact to almost exactly 2.0) in addition to electrons in the CC region. This picture seems to [&hellip;]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1243\" \/>\n<meta property=\"og:site_name\" content=\"Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"article:published_time\" content=\"2009-12-05T13:11:14+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2009-12-05T19:23:13+00:00\" \/>\n<meta property=\"og:image\" content=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/12\/CSOTf.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":"The nature of the C\u2261S Triple bond: Part 2 - 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=1243","og_locale":"en_GB","og_type":"article","og_title":"The nature of the C\u2261S Triple bond: Part 2 - Henry Rzepa&#039;s Blog","og_description":"In my first post on this theme, an ELF (Electron localization function) analysis of the bonding in the molecule HO-S\u2261C-H (DOI: 10.1002\/anie.200903969) was presented. This analysis identified a lone pair of electrons localized on the carbon (integrating in fact to almost exactly 2.0) in addition to electrons in the CC region. This picture seems to [&hellip;]","og_url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1243","og_site_name":"Henry Rzepa&#039;s Blog","article_published_time":"2009-12-05T13:11:14+00:00","article_modified_time":"2009-12-05T19:23:13+00:00","og_image":[{"url":"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/12\/CSOTf.jpg","type":"","width":"","height":""}],"author":"Henry Rzepa","twitter_card":"summary_large_image","twitter_misc":{"Written by":"Henry Rzepa","Estimated reading time":"2 minutes"},"schema":{"@context":"https:\/\/schema.org","@graph":[{"@type":"Article","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1243#article","isPartOf":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1243"},"author":{"name":"Henry Rzepa","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/#\/schema\/person\/2b40f7b9c872a4dc1547e040a11b6281"},"headline":"The nature of the C\u2261S Triple bond: Part 2","datePublished":"2009-12-05T13:11:14+00:00","dateModified":"2009-12-05T19:23:13+00:00","mainEntityOfPage":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1243"},"wordCount":502,"commentCount":3,"image":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1243#primaryimage"},"thumbnailUrl":"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/12\/CSOTf.jpg","keywords":["Hypervalency","Interesting chemistry","large interaction energy"],"articleSection":["Hypervalency","Interesting chemistry"],"inLanguage":"en-GB","potentialAction":[{"@type":"CommentAction","name":"Comment","target":["https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1243#respond"]}]},{"@type":"WebPage","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1243","url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1243","name":"The nature of the C\u2261S Triple bond: Part 2 - 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By replacing the HO group by one with greater \u03c3-electron withdrawing propensity, the stereo-electronic effect between\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":"The H2BSCH molecule. Click for 3D.","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/12\/CSBH2.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":1210,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1210","url_meta":{"origin":1243,"position":1},"title":"The nature of the C\u2261S triple bond","author":"Henry Rzepa","date":"December 1, 2009","format":false,"excerpt":"Steve Bachrach has just blogged on a recent article (DOI: 10.1002\/anie.200903969) claiming the isolation of a compound with a C\u2261S triple bond; Steve notes that Schreiner and co claim a \u201cstructure with a rather strong CS double bond or a weak triple bond\u201d. With this size of molecule, the proverbial\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":"A compound with a CS triple bond","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/12\/CSCC.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":1347,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1347","url_meta":{"origin":1243,"position":2},"title":"M\u00e9nage \u00e0 deux: Non-classical SC bonds.","author":"Henry Rzepa","date":"December 30, 2009","format":false,"excerpt":"A previous post posed the question; during the transformation of one molecule to another, what is the maximum number of electron pairs that can simultaneously move either to or from any one atom-pair bond as part of the reaction? A rather artificial example (atom-swapping between three nitrosonium cations) was used\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\/2009\/12\/SF3.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":23588,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=23588","url_meta":{"origin":1243,"position":3},"title":"Two new reality-based suggestions for molecules with a metal M\u2a78C quadruple bond.","author":"Henry Rzepa","date":"May 8, 2021","format":false,"excerpt":"Following from much discussion over the last decade about the nature of C2, a diatomic molecule which some have suggested sustains a quadruple bond between the two carbon atoms, new ideas are now appearing for molecules in which such a bond may also exist between carbon and a transition metal\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\/2021\/05\/Screenshot-702-300x63.jpg?resize=350%2C200&ssl=1","width":350,"height":200},"classes":[]},{"id":19251,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=19251","url_meta":{"origin":1243,"position":4},"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":10801,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=10801","url_meta":{"origin":1243,"position":5},"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":[]}],"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\/1243","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=1243"}],"version-history":[{"count":0,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/1243\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=1243"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=1243"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=1243"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=1243"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}