{"id":1210,"date":"2009-12-01T12:55:59","date_gmt":"2009-12-01T11:55:59","guid":{"rendered":"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1210"},"modified":"2010-06-24T07:40:00","modified_gmt":"2010-06-24T06:40:00","slug":"the-nature-of-the-cs-triple-bond","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1210","title":{"rendered":"The nature of the C\u2261S triple bond"},"content":{"rendered":"<div class=\"kcite-section\" kcite-section-id=\"1210\">\n<p><a href=\"http:\/\/comporgchem.com\/blog\/?p=510\" target=\"_blank\">Steve Bachrach has just blogged<\/a> on a recent article (DOI: <a href=\"http:\/\/dx.doi.org\/10.1002\/anie.200903969\">10.1002\/anie.200903969<\/a>) claiming the isolation of a compound with a C\u2261S triple bond;<\/p>\n<div id=\"attachment_1211\" style=\"width: 211px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-1211\" class=\"size-full wp-image-1211\" title=\"CSCC\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/12\/CSCC.jpg\" alt=\"A compound with a CS triple bond\" width=\"201\" height=\"101\" \/><p id=\"caption-attachment-1211\" class=\"wp-caption-text\">A compound with a C\u2261S triple bond<\/p><\/div>\n<p>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 kitchen sink can be thrown at the analysis of the bonding. But one technique that was NOT applied is ELF (see the <a href=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1183\" target=\"_blank\">earlier post<\/a> using ELF to analyze the bonding in MgPh<sub>2<\/sub>). So here is such an analysis, computed for the CCSD\/cc-pVTZ wavefunction at the geometry reported in the publication (see also DOI: <a href=\"http:\/\/hdl.handle.net\/10042\/to-2980\" target=\"references\">10042\/to-2980<\/a>). The (centroids of the) synaptic basins are the small purple spheres.<\/p>\n<p><div id=\"attachment_1213\" style=\"width: 360px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-1213\" class=\"size-full wp-image-1213\" title=\"CSCC-elf\" onclick=\"jmolInitialize('..\/Jmol\/');jmolSetAppletColor('yellow');jmolApplet([450,450],'load wp-content\/uploads\/2009\/12\/CSCC-elf.mol;zoom 120;spin 3;set fontscaling TRUE; font label 14;select atomno=10;label %A 2.36;select atomno=11;label %A 2.0;');\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/12\/CSCC-elf.jpg\" alt=\"ELF analysis of the bonding in HOCCH. Click for 3D\" width=\"350\" height=\"238\" \/><p id=\"caption-attachment-1213\" class=\"wp-caption-text\">ELF analysis of the bonding in HOS\u2261CH. Click for 3D<\/p><\/div>The key (disynaptic) basin is labelled <strong>10<\/strong>, and it integrates to 2.36 electrons, rather far from the 6 electrons which might be expected for a triple bond! Its centroid is also significantly off-centre from the S-C bond. Basin <strong>11<\/strong> integrates to 2.01 electrons; it resembles a lone pair on the carbon, although the ELF analysis actually labels it a S-C disynaptic basin. It approximately maps to the HOMO orbital. Monosynaptic basin <strong>9<\/strong> encompases the two formal lone pairs on the sulfur, and it integrates to 3.59e (quite often, what we regard as separate, <em>rabbit-ear<\/em>, lone pairs on an atom manifest only as a single monosynaptic basin). Completing the analysis are two further monosynaptic basins <strong>6<\/strong> and <strong>7<\/strong>, which represent lone pairs on the oxygen (2.45e each) and the disynaptic basin <strong>8<\/strong> (1.1e).<\/p>\n<p>Bonding, much like the Humpty-Dumpty meaning, is very much what you want it to be! But in this case, one has to ask whether the description of the bonding in the C\u2261S region really is best described as a weak triple bond, or even a strong double bond, or whether the nominal six electrons of the triple bond split into two regions, one clearly bonding, the other more non-bonding.<\/p>\n<!-- kcite active, but no citations found -->\n<\/div> <!-- kcite-section 1210 -->","protected":false},"excerpt":{"rendered":"<p>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 kitchen sink can be thrown [&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":[2649,2648,161,20],"ppma_author":[2661],"class_list":["post-1210","post","type-post","status-publish","format-standard","hentry","category-hypervalency","category-interesting-chemistry","tag-hypervalency","tag-interesting-chemistry","tag-schreiner-and-co","tag-steve-bachrach"],"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 - 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=1210\" \/>\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 - Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"og:description\" content=\"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 kitchen sink can be thrown [&hellip;]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1210\" \/>\n<meta property=\"og:site_name\" content=\"Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"article:published_time\" content=\"2009-12-01T11:55:59+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2010-06-24T06:40:00+00:00\" \/>\n<meta property=\"og:image\" content=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/12\/CSCC.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 - 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=1210","og_locale":"en_GB","og_type":"article","og_title":"The nature of the C\u2261S triple bond - Henry Rzepa&#039;s Blog","og_description":"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 kitchen sink can be thrown [&hellip;]","og_url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1210","og_site_name":"Henry Rzepa&#039;s Blog","article_published_time":"2009-12-01T11:55:59+00:00","article_modified_time":"2010-06-24T06:40:00+00:00","og_image":[{"url":"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/12\/CSCC.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=1210#article","isPartOf":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1210"},"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","datePublished":"2009-12-01T11:55:59+00:00","dateModified":"2010-06-24T06:40:00+00:00","mainEntityOfPage":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1210"},"wordCount":353,"commentCount":9,"image":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1210#primaryimage"},"thumbnailUrl":"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/12\/CSCC.jpg","keywords":["Hypervalency","Interesting chemistry","Schreiner and co","Steve Bachrach"],"articleSection":["Hypervalency","Interesting chemistry"],"inLanguage":"en-GB","potentialAction":[{"@type":"CommentAction","name":"Comment","target":["https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1210#respond"]}]},{"@type":"WebPage","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1210","url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1210","name":"The nature of the C\u2261S triple bond - 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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\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":"ELF analysis for H-C\u2261S-OTf","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/12\/CSOTf.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":1210,"position":1},"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":1103,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1103","url_meta":{"origin":1210,"position":2},"title":"Hypervalency: a reality check","author":"Henry Rzepa","date":"October 5, 2009","format":false,"excerpt":"We have seen in the series of posts on the topic of hypervalency\u00a0how the first row main group elements such as\u00a0Be, B, C and N can sustain apparent hypercoordination and arguably hypervalency. 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":3546,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=3546","url_meta":{"origin":1210,"position":3},"title":"Triple metal delight","author":"Henry Rzepa","date":"March 1, 2011","format":false,"excerpt":"Much like chocolate, some of us metallaholics cannot get enough. So WUQXIP proved an irresistible frolic (DOI: 10.1021\/om020789h). Let us start with benzene. \u00a0It can have metals added in two ways, whilst preserving its essential aromaticity. Making a metal sandwich is of course very well known, ferrocene being the first\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.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/03\/metallocene.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":1546,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1546","url_meta":{"origin":1210,"position":4},"title":"Blisteringly bent (quadruple) bonds","author":"Henry Rzepa","date":"January 23, 2010","format":false,"excerpt":"So ingrained is the habit to think of a bond as a simple straight line connecting two atoms, that we rarely ask ourselves if they are bent, and if so, by how much (and indeed, does it matter?). Well Hursthouse, Malik, and Sales, as long ago as 1978, asked just\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\/01\/Cr-Cr.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":1423,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1423","url_meta":{"origin":1210,"position":5},"title":"Contriving aromaticity from S\u2261C Triple bonds","author":"Henry Rzepa","date":"January 1, 2010","format":false,"excerpt":"In the previous post, the molecule F3S-C\u2261SF3 was found to exhibit a valence bond isomerism, one of the S-C bonds being single, the other triple, and with a large barrier (~31 kcal\/mol, \u03bd 284i cm-1) to interconversion of the two valence-bond forms. So an interesting extension of this phenomenon is\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\/01\/S3C3F6.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\/1210","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=1210"}],"version-history":[{"count":0,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/1210\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=1210"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=1210"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=1210"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=1210"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}