{"id":8337,"date":"2012-11-20T08:27:47","date_gmt":"2012-11-20T08:27:47","guid":{"rendered":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=8337"},"modified":"2012-11-20T16:26:56","modified_gmt":"2012-11-20T16:26:56","slug":"a-chiral-molecular-wire","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=8337","title":{"rendered":"A chiral molecular wire."},"content":{"rendered":"<div class=\"kcite-section\" kcite-section-id=\"8337\">\n<p>More than 60 million molecules are known, and many are fascinating. But beauty is in the eye of the beholder. Thus it was that I came across the attached molecule<span id=\"cite_ITEM-8337-0\" name=\"citation\"><a href=\"#ITEM-8337-0\">[1]<\/a><\/span>. It struck me immediately as, well, beautiful!<\/p>\n<div id=\"attachment_8338\" style=\"width: 305px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-8338\" class=\"size-full wp-image-8338\" title=\"GOCTOH\" onclick=\"jmolInitialize('..\/Jmol\/');jmolSetAppletColor('white');jmolApplet([800,800],'load wp-content\/uploads\/2012\/11\/GOCTOH-D4.mol2;measure 3 4;measure 3 2;');\" src=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2012\/11\/GOCTOH.jpg\" alt=\"\" width=\"295\" height=\"296\" \/><p id=\"caption-attachment-8338\" class=\"wp-caption-text\">GOCTOH. Click for 3D.<\/p><\/div>\n<p>This is one that comes to life in 3D and I strongly urge you to inspect it as such by clicking on the above. Why is it so interesting? Well, it has as its backbone a linear array of seven Nickel atoms. The Ni&#8230;Ni distances are around 2.2-2.3\u00c5, and this &#8220;wire&#8221; is wrapped with a square planar arrangement of nitrogen atoms deriving from the ligand.<\/p>\n<p>But that is not just where I perceived its beauty. The molecule has D<sub>4<\/sub> symmetry, and is therefore dissymetric (chiral). The ligands wrap themselves around the metal wire in a helical arrangement. Oddly, the original authors who reported this lovely molecule make little (nothing?) of this aspect. Can it be resolved for example? Can it recognise other chiral molecules? What are its chiroptical properties (optical rotation, circular dichroism spectra etc)? Anyway enough from me; just go and enjoy this gem!\u00a0<\/p>\n<p><script type=\"text\/javascript\">\/\/ < ![CDATA[\nvar transformBallAndStick2 = new ChemDoodle.TransformCanvas3D('transformBallAndStick2', 450, 450);         transformBallAndStick2.specs.set3DRepresentation('Ball and Stick');         transformBallAndStick2.specs.backgroundColor = 'red';         var molFile = httpGet( 'wp-content\/uploads\/2012\/11\/GOCTOH-D4.mol' );         var molecule = ChemDoodle.readMOL(molFile, 2);         transformBallAndStick2.loadMolecule(molecule);\n\/\/ ]]><\/script><\/p>\n<h2>References<\/h2>\n    <ol class=\"kcite-bibliography csl-bib-body\"><li id=\"ITEM-8337-0\">S. Lai, T. Lin, Y. Chen, C. Wang, G. Lee, M. Yang, M. Leung, and S. Peng, \"Metal String Complexes:\u2009 Synthesis and Crystal Structure of [Ni&lt;sub&gt;4&lt;\/sub&gt;(\u03bc&lt;sub&gt;4&lt;\/sub&gt;-phdpda)&lt;sub&gt;4&lt;\/sub&gt;] and [Ni&lt;sub&gt;7&lt;\/sub&gt;(\u03bc&lt;sub&gt;7&lt;\/sub&gt;-teptra)&lt;sub&gt;4&lt;\/sub&gt;Cl&lt;sub&gt;2&lt;\/sub&gt;] (H&lt;sub&gt;2&lt;\/sub&gt;phdpda = &lt;i&gt;N&lt;\/i&gt;-Phenyldipyridyldiamine and H&lt;sub&gt;3&lt;\/sub&gt;teptra = Tetrapyridyltriamine)\", <i>Journal of the American Chemical Society<\/i>, vol. 121, pp. 250-251, 1998. <a href=\"https:\/\/doi.org\/10.1021\/ja982065w\">https:\/\/doi.org\/10.1021\/ja982065w<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> <!-- kcite-section 8337 -->","protected":false},"excerpt":{"rendered":"<p>More than 60 million molecules are known, and many are fascinating. But beauty is in the eye of the beholder. Thus it was that I came across the attached molecule. It struck me immediately as, well, beautiful! This is one that comes to life in 3D and I strongly urge you to inspect it as [&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_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":[4],"tags":[945],"ppma_author":[2661],"class_list":["post-8337","post","type-post","status-publish","format-standard","hentry","category-interesting-chemistry","tag-metal-wire"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.6 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>A chiral molecular wire. - 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=8337\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"A chiral molecular wire. - Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"og:description\" content=\"More than 60 million molecules are known, and many are fascinating. But beauty is in the eye of the beholder. Thus it was that I came across the attached molecule. It struck me immediately as, well, beautiful! This is one that comes to life in 3D and I strongly urge you to inspect it as [&hellip;]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=8337\" \/>\n<meta property=\"og:site_name\" content=\"Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"article:published_time\" content=\"2012-11-20T08:27:47+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2012-11-20T16:26:56+00:00\" \/>\n<meta property=\"og:image\" content=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2012\/11\/GOCTOH.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=\"1 minute\" \/>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"A chiral molecular wire. - 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=8337","og_locale":"en_GB","og_type":"article","og_title":"A chiral molecular wire. - Henry Rzepa&#039;s Blog","og_description":"More than 60 million molecules are known, and many are fascinating. 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Gizmodo wanted to know if I could provide an (almost)\u2020 instant\u2021 quote. After a few days, this report of a stable compound of helium\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":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/02\/101-1024x658.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":19499,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=19499","url_meta":{"origin":8337,"position":1},"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":9322,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=9322","url_meta":{"origin":8337,"position":2},"title":"Anapolar ring currents: a [144]-Annulene.","author":"Henry Rzepa","date":"February 1, 2013","format":false,"excerpt":"This is a recently published (hypothetical) molecule which has such unusual properties that I cannot resist sharing it with you. It is an annulene with 144 all-cis CH groups, being a (very) much larger cousin of (also hypothetical) systems mooted in 2009,. One fascinating novel aspect of Berger's work is\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":"A 144-carbon annulene. Click for  3D.","src":"https:\/\/i0.wp.com\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/02\/C144.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":9778,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=9778","url_meta":{"origin":8337,"position":3},"title":"Lithiation of heteroaromatic rings: analogy to electrophilic substitution?","author":"Henry Rzepa","date":"March 16, 2013","format":false,"excerpt":"Functionalisation of a (hetero)aromatic ring by selectively (directedly) removing protons using the metal lithium is a relative mechanistic newcomer, compared to the pantheon of knowledge on\u00a0aromatic electrophilic substitution. Investigating the mechanism using quantum calculations poses some interesting challenges, ones I have not previously discussed on this blog. My model will\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":"SUHBEC. CLICK FOR 3D.","src":"https:\/\/i0.wp.com\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/03\/SUHBEC.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":22996,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=22996","url_meta":{"origin":8337,"position":4},"title":"An interesting aromatic molecule found in Titan&#8217;s atmosphere: Cyclopropenylidene","author":"Henry Rzepa","date":"November 7, 2020","format":false,"excerpt":"Cyclopropenylidene must be the smallest molecule to be aromatic due to \u03c0-electrons, with just three carbon atoms and two hydrogen atoms. It has now been detected in the atmosphere of Titan, one of Saturn's moons and joins benzene, another aromatic molecule together with the protonated version of cyclopropenylidene, C3H3+ also\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":9973,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=9973","url_meta":{"origin":8337,"position":5},"title":"A (very) short history of shared-electron bonds.","author":"Henry Rzepa","date":"March 26, 2013","format":false,"excerpt":"The concept of a shared electron bond and its property of an order is almost 100 years old in modern form, when G. N. Lewis suggested a model for single and double bonds that involved sharing either 2 or 4 electrons between a pair of atoms. We tend to think\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":"Click for  3D","src":"https:\/\/i0.wp.com\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/03\/PYRDRE.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\/8337","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=8337"}],"version-history":[{"count":13,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/8337\/revisions"}],"predecessor-version":[{"id":8371,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/8337\/revisions\/8371"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=8337"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=8337"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=8337"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=8337"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}