{"id":11538,"date":"2013-11-05T17:40:43","date_gmt":"2013-11-05T17:40:43","guid":{"rendered":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=11538"},"modified":"2013-11-17T17:49:32","modified_gmt":"2013-11-17T17:49:32","slug":"multiple-personalities-of-magnesium","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=11538","title":{"rendered":"Multiple personalities of  Magnesium."},"content":{"rendered":"<div class=\"kcite-section\" kcite-section-id=\"11538\">\n<p>The following is a short question in a problem sheet associated with introductory organic chemistry.<\/p>\n<ul>\n<li><strong>Q<\/strong>: &#8220;<em>Show curly arrows for the formation of the product of the following reaction, together with a Lewis representation of that product: Et<sub>2<\/sub>O + MgBr<sub>2<\/sub><\/em>&#8220;.<\/li>\n<li><strong>A<\/strong>:\u00a0<em>Et<sub>2<\/sub>O<sup>+<\/sup>-Mg<sup>&#8211;<\/sup>Br<sub>2<\/sub><\/em> (a product by the way that is known as magnesium bromide ethyl etherate, and which is commercially available as a solution).<\/li>\n<\/ul>\n<p>First a few tutor-like comments. The Mg is tri-coordinate in this simple representation, and if we assume that the bonds are covalent, has six electrons in the Mg valence shell. In modern notation, the Mg has a formal charge of -1 and the oxygen +1. The Mg thus does not have a filled 3s\/3p valence shell, which would be eight.\u00a0But few (students or tutors) go on to apply a reality check.\u00a0So here is one.<\/p>\n<p>The reality check involves a search for a crystal structure, which is really trivial to set up. And what we find are the following.<\/p>\n<ol>\n<li>The first hit with exactly this stoichiometry has the CCDC code\u00a0<strong>TOQKIT<\/strong> and a polymeric structure as below. Each Mg is coordinated by four (bridged) bromines and one oxygen, giving <em>trigonal bipyramidal<\/em> penta-coordination. The valence electron count at Mg is now eight, but distributed around five bonds, not four. Since we no longer have formal Lewis two-electron covalent bonds, it is difficult to assign a Lewis-like charge to the atoms.\u00a0<br \/>\n<div id=\"attachment_11541\" style=\"width: 317px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-11541\" class=\" wp-image-11541 \" onclick=\"jmolInitialize('..\/Jmol\/','JmolAppletSigned.jar');jmolSetAppletColor('white');jmolApplet([450,450],'load wp-content\/uploads\/2013\/11\/TOQKIT.mol;');\" alt=\"Click for  3D\" src=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/11\/TOQKIT.jpg\" width=\"307\" height=\"206\" \/><p id=\"caption-attachment-11541\" class=\"wp-caption-text\">Click for 3D<\/p><\/div>\n<\/li>\n<li>The next hit actually corresponds to the stoichiometry 2R<sub>2<\/sub>O + MgBr<sub>2<\/sub> (R=thf). This again is polymeric, but differs from the first structure in having <em>octahedral<\/em> Mg (six coordination).<br \/>\n<div id=\"attachment_11544\" style=\"width: 303px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-11544\" class=\" wp-image-11544  \" onclick=\"jmolInitialize('..\/Jmol\/','JmolAppletSigned.jar');jmolSetAppletColor('white');jmolApplet([450,450],'load wp-content\/uploads\/2013\/11\/MGBEET.mol2;');\" alt=\"Click for  3D.\" src=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/11\/MGBEET.jpg\" width=\"293\" height=\"290\" \/><p id=\"caption-attachment-11544\" class=\"wp-caption-text\">Click for 3D.<\/p><\/div>\n<\/li>\n<li>OK, even more ether: 4R<sub>2<\/sub>O + MgBr<sub>2<\/sub>. Finally, non polymeric but again with six-coordinate <em>octahedral<\/em> Mg. The Mg again has a filled valence octet, and again the bonds are not two-electron ones, hence no charges are attempted.\u00a0So just a change in the stoichiometry can result in fascinating changes to the resulting structure.<br \/>\n<div id=\"attachment_11545\" style=\"width: 317px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-11545\" class=\" wp-image-11545  \" onclick=\"jmolInitialize('..\/Jmol\/','JmolAppletSigned.jar');jmolSetAppletColor('white');jmolApplet([450,450],'load wp-content\/uploads\/2013\/11\/ZZZVBQ.mol2;');\" alt=\"Click for  3D\" src=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/11\/ZZZ.jpg\" width=\"307\" height=\"302\" \/><p id=\"caption-attachment-11545\" class=\"wp-caption-text\">Click for 3D<\/p><\/div>\n<\/li>\n<li>Finally, a variation; benzyl magnesium bromide (a Grignard reagent) shows<em> tetrahedral<\/em> coordination.<\/li>\n<\/ol>\n<div id=\"attachment_11557\" style=\"width: 312px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-11557\" class=\" wp-image-11557  \" onclick=\"jmolInitialize('..\/Jmol\/','JmolAppletSigned.jar');jmolSetAppletColor('white');jmolApplet([450,450],'load wp-content\/uploads\/2013\/11\/XECTOQ.mol2;');\" alt=\"Click for 3D\" src=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/11\/XECTOQ.jpg\" width=\"302\" height=\"233\" \/><p id=\"caption-attachment-11557\" class=\"wp-caption-text\">Click for 3D<\/p><\/div>\n<p>Students (and tutors) who get as far as this are amply rewarded I hope!<\/p>\n<!-- kcite active, but no citations found -->\n<\/div> <!-- kcite-section 11538 -->","protected":false},"excerpt":{"rendered":"<p>The following is a short question in a problem sheet associated with introductory organic chemistry. Q: &#8220;Show curly arrows for the formation of the product of the following reaction, together with a Lewis representation of that product: Et2O + MgBr2&#8220;. A:\u00a0Et2O+-Mg&#8211;Br2 (a product by the way that is known as magnesium bromide ethyl etherate, and [&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":[4],"tags":[1153,1151,74,1152,196],"ppma_author":[2661],"class_list":["post-11538","post","type-post","status-publish","format-standard","hentry","category-interesting-chemistry","tag-grignard","tag-octahedral","tag-pence","tag-pentagonalbipyramid","tag-tetrahedral"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.5 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Multiple personalities of Magnesium. - 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=11538\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Multiple personalities of Magnesium. - Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"og:description\" content=\"The following is a short question in a problem sheet associated with introductory organic chemistry. Q: &#8220;Show curly arrows for the formation of the product of the following reaction, together with a Lewis representation of that product: Et2O + MgBr2&#8220;. A:\u00a0Et2O+-Mg&#8211;Br2 (a product by the way that is known as magnesium bromide ethyl etherate, and [&hellip;]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=11538\" \/>\n<meta property=\"og:site_name\" content=\"Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"article:published_time\" content=\"2013-11-05T17:40:43+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2013-11-17T17:49:32+00:00\" \/>\n<meta property=\"og:image\" content=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/11\/TOQKIT.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":"Multiple personalities of Magnesium. - 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=11538","og_locale":"en_GB","og_type":"article","og_title":"Multiple personalities of Magnesium. - Henry Rzepa&#039;s Blog","og_description":"The following is a short question in a problem sheet associated with introductory organic chemistry. 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A:\u00a0Et2O+-Mg&#8211;Br2 (a product by the way that is known as magnesium bromide ethyl etherate, and [&hellip;]","og_url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=11538","og_site_name":"Henry Rzepa&#039;s Blog","article_published_time":"2013-11-05T17:40:43+00:00","article_modified_time":"2013-11-17T17:49:32+00:00","og_image":[{"url":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/11\/TOQKIT.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=11538#article","isPartOf":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=11538"},"author":{"name":"Henry Rzepa","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/#\/schema\/person\/2b40f7b9c872a4dc1547e040a11b6281"},"headline":"Multiple personalities of Magnesium.","datePublished":"2013-11-05T17:40:43+00:00","dateModified":"2013-11-17T17:49:32+00:00","mainEntityOfPage":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=11538"},"wordCount":387,"commentCount":2,"image":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=11538#primaryimage"},"thumbnailUrl":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/11\/TOQKIT.jpg","keywords":["Grignard","octahedral","pence","pentagonalbipyramid","tetrahedral"],"articleSection":["Interesting chemistry"],"inLanguage":"en-GB","potentialAction":[{"@type":"CommentAction","name":"Comment","target":["https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=11538#respond"]}]},{"@type":"WebPage","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=11538","url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=11538","name":"Multiple personalities of Magnesium. - 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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":2559,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=2559","url_meta":{"origin":11538,"position":1},"title":"(Almost) 100 years of Lewis structures: are they still fit for purpose?","author":"Henry Rzepa","date":"September 27, 2010","format":false,"excerpt":"The molecule below was characterised in 1996 (DOI: 10.1246\/cl.1996.489) and given the name tris(dithiolene)vanadium (IV). No attempt was made in the original article to give this molecule a Lewis structure using Lewis electron pair bonds. This blog will explore some of the issues that arise when this is attempted.1 The\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":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2010\/09\/V1.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":15552,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=15552","url_meta":{"origin":11538,"position":2},"title":"VSEPR Theory: A closer look at trifluorothionitrile, NSF3.","author":"Henry Rzepa","date":"January 16, 2016","format":false,"excerpt":"The post on applying VSEPR (\"valence shell electron pair repulsion\") theory to the geometry of ClF3\u00a0has proved perennially popular. So here is a follow-up on another little molecue,\u00a0F3SN. As the name implies, it is often represented with an\u00a0S\u2261N bond. Here I take a look at the conventional analysis. This 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":"","width":0,"height":0},"classes":[]},{"id":19472,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=19472","url_meta":{"origin":11538,"position":3},"title":"What are the highest bond indices for main group and transition group elements?","author":"Henry Rzepa","date":"March 4, 2018","format":false,"excerpt":"A bond index (BI) approximately measures the totals of the bond orders at any given atom in a molecule. Here I ponder what the maximum values might be for elements with filled valence shells. Following Lewis in 1916 who proposed that the full valence shell for main group elements should\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":19499,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=19499","url_meta":{"origin":11538,"position":4},"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":30890,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=30890","url_meta":{"origin":11538,"position":5},"title":"Valence bond representations with +ve charges on adjacent atoms? An odd titanium complex analysed.","author":"Henry Rzepa","date":"March 8, 2026","format":false,"excerpt":"A few posts back, I contemplated the curly arrows appropriate for the formation of nitrosobenzene dimer from nitrosobenzene, and commented on the odd nature of the N=N double bond formed in this process.. Odd, because the valence bond representation of this dimer (1 below) has two formally positive adjacent nitrogen\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","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\/11538","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=11538"}],"version-history":[{"count":18,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/11538\/revisions"}],"predecessor-version":[{"id":11672,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/11538\/revisions\/11672"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=11538"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=11538"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=11538"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=11538"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}