{"id":3546,"date":"2011-03-01T19:46:17","date_gmt":"2011-03-01T19:46:17","guid":{"rendered":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=3546"},"modified":"2011-07-10T07:32:55","modified_gmt":"2011-07-10T07:32:55","slug":"triple-metal-delight","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=3546","title":{"rendered":"Triple metal delight"},"content":{"rendered":"<div class=\"kcite-section\" kcite-section-id=\"3546\">\n<p>Much like chocolate, some of us metallaholics cannot get enough. So WUQXIP proved an irresistible frolic (DOI: <a href=\"http:\/\/dx.doi.org\/10.1021\/om020789h\" target=\"_blank\">10.1021\/om020789h<\/a>). Let us start with benzene. \u00a0It can have metals added in two ways, whilst preserving its essential aromaticity.<\/p>\n<div id=\"attachment_3547\" style=\"width: 275px\" class=\"wp-caption aligncenter\"><a href=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/03\/metallocene.jpg\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-3547\" class=\"size-full wp-image-3547\" title=\"metallocene\" src=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/03\/metallocene.jpg\" alt=\"\" width=\"265\" height=\"322\" srcset=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/03\/metallocene.jpg 1059w, https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/03\/metallocene-247x300.jpg 247w, https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/03\/metallocene-843x1024.jpg 843w\" sizes=\"auto, (max-width: 265px) 100vw, 265px\" \/><\/a><p id=\"caption-attachment-3547\" class=\"wp-caption-text\">Triple metal delight.<\/p><\/div>\n<p>Making a metal sandwich is of course very well known, ferrocene being the first example where the bonding was identified. Replacing a carbon with a metal is a little more recent, having been suggested by Hoffmann in 1979. This is known as a metallabenzene. The compound below combines both features.<\/p>\n<p><div id=\"attachment_3548\" style=\"width: 310px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-3548\" class=\"size-full wp-image-3548\" title=\"WUQXIP\" onclick=\"jmolInitialize('..\/Jmol\/',true);jmolSetAppletColor('yellow');jmolApplet([600,600],'load wp-content\/uploads\/2011\/03\/WUQXIP.cif;zoom 90;measure 19 1;spin 2;');\" src=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/03\/WUQXIP.jpg\" alt=\"\" width=\"300\" height=\"283\" \/><p id=\"caption-attachment-3548\" class=\"wp-caption-text\">WUQXIP. Click for 3D<\/p><\/div>The metal is Ruthenium (coloured purple above)\u00a0in the same column of the periodic table as Iron. What of the triple delight? Well, the compound really is more than the sum of its parts. The original authors (Ulrike Effertz, Ulli Englert, Frank Podewils, Albrecht Salzer, Trixie Wagner and Martin Kaupp) speculated about whether there might be bonding between any of the Ru atoms. You see an apparent mutual attraction meant that they were rather closer than the sum of their van der Waals radii would suggest they should be. Their relative orientation (they could easily have avoided each other) was very suggestive. So a metal-metal bond would be our third delight! \u00a0To find out, the authors noted above did an ELF analysis. I have repeated this and the result is shown below.<\/p>\n<p><div id=\"attachment_3561\" style=\"width: 234px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-3561\" class=\"size-full wp-image-3561\" title=\"WUQXIP-elf\" onclick=\"jmolInitialize('..\/Jmol\/',true);jmolSetAppletColor('yellow');jmolApplet([600,600],'load wp-content\/uploads\/2011\/03\/WUQXIP_bas.mol2;select atomno=59;halo on;');\" src=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/03\/WUQXIP-elf.jpg\" alt=\"\" width=\"224\" height=\"221\" srcset=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/03\/WUQXIP-elf.jpg 673w, https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/03\/WUQXIP-elf-300x295.jpg 300w\" sizes=\"auto, (max-width: 224px) 100vw, 224px\" \/><p id=\"caption-attachment-3561\" class=\"wp-caption-text\">ELF basins for WUQXIP. Click for 3D<\/p><\/div>A <strong>trisynaptic<\/strong> basin is revealed between the three ruthenium atoms; a classic example of a three-centre bond. It integrates to 0.64 electrons (<a href=\"http:\/\/hdl.handle.net\/10042\/to-7392\" target=\"_blank\">B3PW91\/Dev-2<\/a>-pVDZ), so its fairly weak. But still strong enough to bring the three ruthenium atoms closer together. A true triple metal bonding delight!<\/p>\n<p>&nbsp;<\/p>\n<!-- kcite active, but no citations found -->\n<\/div> <!-- kcite-section 3546 -->","protected":false},"excerpt":{"rendered":"<p>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 example where the bonding was [&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_feature_clip_id":0,"_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":[459,455,460,157,463,465,461,422,420,421,462,464,458,456,457],"ppma_author":[2661],"class_list":["post-3546","post","type-post","status-publish","format-standard","hentry","category-hypervalency","tag-albrecht-salzer","tag-frank-podewils","tag-martin-kaupp","tag-metal","tag-metal-delight","tag-metal-sandwich","tag-metal-metal-bond","tag-metallabenzene","tag-metallocene","tag-three-centre-bonding","tag-triple-metal-bonding-delight","tag-triple-metal-delight","tag-trixie-wagner","tag-ulli-englert","tag-ulrike-effertz"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.9 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Triple metal delight - 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=3546\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Triple metal delight - Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"og:description\" content=\"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. 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Making a metal sandwich is of course very well known, ferrocene being the first example where the bonding was [&hellip;]","og_url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=3546","og_site_name":"Henry Rzepa&#039;s Blog","article_published_time":"2011-03-01T19:46:17+00:00","article_modified_time":"2011-07-10T07:32:55+00:00","og_image":[{"url":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/03\/metallocene.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=3546#article","isPartOf":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=3546"},"author":{"name":"Henry Rzepa","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/#\/schema\/person\/2b40f7b9c872a4dc1547e040a11b6281"},"headline":"Triple metal delight","datePublished":"2011-03-01T19:46:17+00:00","dateModified":"2011-07-10T07:32:55+00:00","mainEntityOfPage":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=3546"},"wordCount":307,"commentCount":0,"image":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=3546#primaryimage"},"thumbnailUrl":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/03\/metallocene.jpg","keywords":["Albrecht Salzer","Frank Podewils","Martin Kaupp","metal","metal delight","metal sandwich","metal-metal bond","metallabenzene","metallocene","three-centre bonding","triple metal bonding delight","Triple metal delight","Trixie Wagner","Ulli Englert","Ulrike Effertz"],"articleSection":["Hypervalency"],"inLanguage":"en-GB","potentialAction":[{"@type":"CommentAction","name":"Comment","target":["https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=3546#respond"]}]},{"@type":"WebPage","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=3546","url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=3546","name":"Triple metal delight - 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I had previously mooted that the Fe\u2a78C combination might be\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-703-1024x818.jpg?resize=350%2C200&ssl=1","width":350,"height":200},"classes":[]},{"id":16518,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=16518","url_meta":{"origin":3546,"position":2},"title":"A wider look at \u03c0-complex metal-alkene (and alkyne) compounds.","author":"Henry Rzepa","date":"June 13, 2016","format":false,"excerpt":"Previously, I looked at the historic origins of the so-called \u03c0-complex theory of metal-alkene complexes. Here I follow this up with some data mining of the crystal structure database for such structures. Alkene-metal \"\u03c0-complexes\" have what might be called a representational problem; they do not happily fit into the standard\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":"","width":0,"height":0},"classes":[]},{"id":30548,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=30548","url_meta":{"origin":3546,"position":3},"title":"Molecules of the year 2025: Benzene-busting inverted sandwich.","author":"Henry Rzepa","date":"January 1, 2026","format":false,"excerpt":"Sandwich compounds are the colloquial term used for molecules where a metal atom such as an iron dication is \"sandwiched\" between two carbon-based rings as ligands, most commonly cyclopentadienyl anion (the \"bread\") as in e.g. Ferrocene - a molecule first discovered in 1951. An \"inverted\" sandwich is where the carbon\u2026","rel":"","context":"In &quot;Interesting chemistry&quot;","block_context":{"text":"Interesting chemistry","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=4"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]},{"id":1183,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1183","url_meta":{"origin":3546,"position":4},"title":"Multi-centre bonding in  the Grignard Reagent","author":"Henry Rzepa","date":"December 1, 2009","format":false,"excerpt":"The Grignard reaction is encountered early on in most chemistry courses, and most labs include the preparation of this reagent, typically by the following reaction: 2PhBr + 2Mg \u2192 2PhMgBr\u00a0\u2194 MgBr2 + Ph2Mg The reagent itself exists as part of an equilibrium, named after Schlenk, in which a significant concentration\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 crystal structure of a di-aryl magnesium. Click to view 3D","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/12\/udaqiz.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":10448,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=10448","url_meta":{"origin":3546,"position":5},"title":"The \u03c0-complex theory of metal-alkene compounds.","author":"Henry Rzepa","date":"May 13, 2013","format":false,"excerpt":"The period 1951--1954 was a golden one for structural chemistry; proteins, DNA, Ferrocene (1952) and the one I discuss here, a bonding model for Zeise's salt (3). In\u00a0\"A review of \u03c0 Complex Theory\",\u00a0 Bull. Soc. Chim. Fr., 1951, 1 8 , C79 (it is not online) M. J. S.\u00a0Dewar\u00a0sets out\u2026","rel":"","context":"In &quot;Interesting chemistry&quot;","block_context":{"text":"Interesting chemistry","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=4"},"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","author_category":"1","first_name":"Henry","last_name":"Rzepa","user_url":"https:\/\/orcid.org\/0000-0002-8635-8390","job_title":"","description":"Henry Rzepa is Emeritus Professor of Computational Chemistry at Imperial College London."}],"_links":{"self":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/3546","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=3546"}],"version-history":[{"count":0,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/3546\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=3546"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=3546"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=3546"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=3546"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}