{"id":5204,"date":"2011-10-21T19:37:47","date_gmt":"2011-10-21T18:37:47","guid":{"rendered":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=5204"},"modified":"2016-05-14T06:46:43","modified_gmt":"2016-05-14T05:46:43","slug":"historical-detective-stories-colourful-crystals","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=5204","title":{"rendered":"Historical detective stories: colourful crystals."},"content":{"rendered":"<div class=\"kcite-section\" kcite-section-id=\"5204\">\n<p>\n\tOrganic chemists have been making (more or less pure) molecules for the best part of 180 years. Occasionally, these ancient samples are unearthed in cupboards, and then the hunt for their origin starts. I have <a href=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=2798\" target=\"_blank\">previously described <\/a>tracking down the structure of a 120 year-old sample of a naphthalene derivative. But I visited a colleague&#39;s office today, and recollected having seen a well-made wooden display cabinet there on a previous visit. Today I took a photo of one of the samples:\n<\/p>\n<div id=\"attachment_5205\" style=\"width: 295px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-5205\" class=\"size-full wp-image-5205  wp-caption aligncenter\" title=\"DSCF8570\" src=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/10\/DSCF8570.jpg\" alt=\"\" width=\"285\" height=\"168\" \/><p id=\"caption-attachment-5205\" class=\"wp-caption-text\">One of the &quot;Hofmann&quot; collection.<\/p><\/div>\n<p>\n\tNo date, no name, but a structure! As I noted before, when it comes to structures, you have to research the conventions (and numbering) used at the time. Thus note the apparent cyclohexane rings, the N(Me)<sub>2<\/sub> group and the lack of stereochemistry around the alkenes. The former dates the sample to before 1950, whilst the use of Me to mean methyl puts it in the 20th century. Which is shame, since it had been known as the &quot;Hofmann&quot; collection, meaning some sort association with <a href=\"tp:\/\/en.wikipedia.org\/wiki\/August_Wilhelm_von_Hofmann\" target=\"_blank\">August von Hofmann<\/a>, the first professor of organic chemistry in the UK, who occupied that position from 1845-1864. Samples that old are very rare. The one above by the way is very deep green (the photo does not do it justice), and very crystalline! Tracing the history of where the display cabinet might have been did indeed reveal that it probably started its life at the same institute as Hofmann was working in (and where I now work), but little more than this was known about it.\n<\/p>\n<p>\n\tA search of the Beilstein database (nowadays known as Reaxys) revealed a collection of samples corresponding to the above structure (with benzenes of course, not cyclohexanes), but co-crystallised with different molecules, and dating from 1921. These were known as the <a href=\"10.1039\/ct9211901500\" target=\"_blank\">Heilbron collection<\/a>, and this was encouraging, since Heilbron was indeed a successor to Hofmann, being active in the 1920s. During his career, he and his students probably made 100s, if not 1000s of compounds, so why did they go to the considerable expense of having beautiful wooden cases built to house these particular samples? Probably because the basic colour varied from yellow to black (perhaps 400nm difference in &lambda;<sub>max<\/sub>)&nbsp;and for which they had no explanation! So, much like some people are cryofrozen in the hope an advanced civilisation might bring them back to life in the future, these samples were mounted in a display cabinet in the hope that someone would find out the origins of their variable colour.\n<\/p>\n<p>\n\tWell, in 1984 (some 63 years after the event)<span id=\"cite_ITEM-5204-0\" name=\"citation\"><a href=\"#ITEM-5204-0\">[1]<\/a><\/span> researchers at the lsrael Institute of Technology, Haifa, came upon the 1921 article (but not the samples; if they read this they might be amazed that these still exist!), repeated (most of the) syntheses, and determined the crystal structure of three of the molecules (but conspicuously not the one above). One 3D structure is shown below. The colours were ascribed to charge-transfer interactions between the components of the molecules.\n<\/p>\n<div id=\"attachment_5208\" style=\"width: 272px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-5208\" alt=\"\" class=\"size-full wp-image-5208  \" height=\"134\" onclick=\"jmolInitialize('..\/Jmol\/',true);jmolSetAppletColor('white');jmolApplet([600,600],'load wp-content\/uploads\/2011\/10\/DADZIR.cif;measure 31 90;measure 35 90;');\" src=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/10\/DADZIR.jpg\" title=\"DADZIR\" width=\"262\" \/><p id=\"caption-attachment-5208\" class=\"wp-caption-text\">DADZIR. Click for 3D<\/p><\/div>\n<p>As I noted previously, it is well worth preserving chemical samples for future generations (and sometimes that generation is 120 years in the future!). Sadly, health and safety aspects (real or imagined) mean that such collections are being lost to posterity at an every increasing rate. Soon, there may be no collections of old chemicals left. That would be indeed a loss to science. So if you know of a lovingly preserved case of old chemicals, go take a look at it. And if it&#39;s in danger of being put in the skip, then rescue it. There is no telling what may be scientifically interesting about it.<\/p>\n<h2>References<\/h2>\n    <ol class=\"kcite-bibliography csl-bib-body\"><li id=\"ITEM-5204-0\">F.H. Herbstein, M. Kapon, G.M. Reisner, and G.M. Rubin, \"Crystallographic studies of the molecular complexes ofE,E-1[p-dimethylaminophenyl]-5-[o-hydroxyphenyl]-penta-1,4-dien-3-one 9DHDK) with chloroform (1:0.4),m-dinitrobenzene (1:1) andp-dimethylaminobenzaldehyde (1:1); the Heilbron complexes\", <i>Journal of Inclusion Phenomena<\/i>, vol. 1, pp. 233-250, 1984. <a href=\"https:\/\/doi.org\/10.1007\/bf00656759\">https:\/\/doi.org\/10.1007\/bf00656759<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> <!-- kcite-section 5204 -->","protected":false},"excerpt":{"rendered":"<p>Organic chemists have been making (more or less pure) molecules for the best part of 180 years. Occasionally, these ancient samples are unearthed in cupboards, and then the hunt for their origin starts. I have previously described tracking down the structure of a 120 year-old sample of a naphthalene derivative. But I visited a colleague&#39;s [&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":[451,700,309,697,699,2651,703,698,702,635,701],"ppma_author":[2661],"class_list":["post-5204","post","type-post","status-publish","format-standard","hentry","category-interesting-chemistry","tag-august-von-hofmann","tag-chemicals","tag-detective","tag-first-professor","tag-haifa","tag-historical","tag-institute-of-technology","tag-professor-of-organic-chemistry-in-the-uk","tag-technion","tag-united-kingdom","tag-worth-preserving-chemical-samples"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Historical detective stories: colourful crystals. - 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=5204\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Historical detective stories: colourful crystals. - Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"og:description\" content=\"Organic chemists have been making (more or less pure) molecules for the best part of 180 years. Occasionally, these ancient samples are unearthed in cupboards, and then the hunt for their origin starts. I have previously described tracking down the structure of a 120 year-old sample of a naphthalene derivative. But I visited a colleague&#039;s [&hellip;]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=5204\" \/>\n<meta property=\"og:site_name\" content=\"Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"article:published_time\" content=\"2011-10-21T18:37:47+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2016-05-14T05:46:43+00:00\" \/>\n<meta property=\"og:image\" content=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/10\/DSCF8570.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=\"3 minutes\" \/>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"Historical detective stories: colourful crystals. - 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=5204","og_locale":"en_GB","og_type":"article","og_title":"Historical detective stories: colourful crystals. - Henry Rzepa&#039;s Blog","og_description":"Organic chemists have been making (more or less pure) molecules for the best part of 180 years. 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Perkin went on to found the British\u2026","rel":"","context":"In &quot;General&quot;","block_context":{"text":"General","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=1"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/02\/220px-Rees1.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":3472,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=3472","url_meta":{"origin":5204,"position":1},"title":"A short history of  molecular modelling: 1860-1890.","author":"Henry Rzepa","date":"February 5, 2011","format":false,"excerpt":"In 1953, the model of the DNA molecule\u00a0led to what has become regarded as the most\u00a0famous scientific diagram\u00a0of the 20th century. It had all started 93 years earlier in\u00a01860, at a time when the tetravalency of carbon was only just established (by William Odling) and the concept of atoms as\u2026","rel":"","context":"In &quot;General&quot;","block_context":{"text":"General","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=1"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/02\/molmod.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":14984,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=14984","url_meta":{"origin":5204,"position":2},"title":"The atom and the molecule: A one-day symposium on 23 March, 2016 celebrating Gilbert N. Lewis.","author":"Henry Rzepa","date":"December 11, 2015","format":false,"excerpt":"You might have noticed the occasional reference here to the upcoming centenary of the publication of Gilbert N. Lewis' famous article entitled \"The atom and the molecule\". A symposium exploring his\u00a0scientific impact and legacy\u00a0will be held in London on March 23, 2016, exactly 70 years to the day since his\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":9754,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=9754","url_meta":{"origin":5204,"position":3},"title":"William Henry Perkin: The site of the factory and the grave.","author":"Henry Rzepa","date":"March 11, 2013","format":false,"excerpt":"William Henry Perkin\u00a0is a local chemical hero of mine. The factory where he founded the British (nay, the World) fine organic chemicals industry is in\u00a0Greenford,\u00a0just up the road from where we live. The factory used to be close to the Black Horse pub (see below) on the banks of 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":"Perkin-Factory-plaque","src":"https:\/\/i0.wp.com\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/03\/Perkin-Factory-plaque.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":2798,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=2798","url_meta":{"origin":5204,"position":4},"title":"A historical detective story: 120 year old crystals","author":"Henry Rzepa","date":"November 17, 2010","format":false,"excerpt":"In 1890, chemists had to work hard to find out what the structures of their molecules were, given they had no access to the plethora of modern techniques we are used to in 2010. For example, how could they be sure what the structure of naphthalene was? Well, two such\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\/11\/trichloronaphthalene1.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":14707,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=14707","url_meta":{"origin":5204,"position":5},"title":"Pierre and Marie Curie.","author":"Henry Rzepa","date":"October 23, 2015","format":false,"excerpt":"I have previously shown the grave of \u00a0William Perkin, a great british organic chemist. On a recent visit to \u00a0Paris, I went to see the crypt in the Panth\u00e9on, the great french secular necropolis. What a contrast to Perkin!\u00a0 The Curies have a crypt all to themselves (VII), and other\u2026","rel":"","context":"In &quot;Historical&quot;","block_context":{"text":"Historical","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=565"},"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\/5204","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=5204"}],"version-history":[{"count":1,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/5204\/revisions"}],"predecessor-version":[{"id":16390,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/5204\/revisions\/16390"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=5204"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=5204"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=5204"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=5204"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}