{"id":5248,"date":"2011-10-26T16:14:08","date_gmt":"2011-10-26T15:14:08","guid":{"rendered":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=5248"},"modified":"2011-10-27T08:41:22","modified_gmt":"2011-10-27T07:41:22","slug":"the-colour-of-purple-is-not-orange-but-mauve","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=5248","title":{"rendered":"The colour of purple is &#8230; not orange but mauve?"},"content":{"rendered":"<div class=\"kcite-section\" kcite-section-id=\"5248\">\n<p>My previous post on the topic of mauveine left the <a href=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=3507\" target=\"_blank\">outcome dangling.<\/a>\u00a0Put simply, \u03bb<sub>max<\/sub> is measured at about 549nm for mauveine A, but was calculated at about 440nm using a modern method for predicting colour (TD-DFT). According to the colour table below, that would make it orange, not mauve. Can the theoretical prediction be out by 110nm, or might it be the structure of the molecule itself that has been wrongly described?<br \/>\n<img decoding=\"async\" class=\"aligncenter\" src=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/03\/colour-table.jpg\" alt=\"colour table\" width=\"400\" \/><\/p>\n<p>A new idea struck me, summarised below. No crystal structure of a mauveine has ever been reported, and so the position of the N-H groups is not determined. It is normally drawn as tautomer <strong>1<\/strong>, but what about tautomers <strong>2-4<\/strong>?<\/p>\n<div id=\"attachment_5249\" style=\"width: 410px\" class=\"wp-caption aligncenter\"><a href=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/10\/mauveine.jpg\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-5249\" class=\"size-full wp-image-5249\" title=\"mauveine\" src=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/10\/mauveine.jpg\" alt=\"\" width=\"400\" height=\"254\" \/><\/a><p id=\"caption-attachment-5249\" class=\"wp-caption-text\">Tautomers of mauveine.<\/p><\/div>\n<p>Following the principle of <a href=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=4952\" target=\"_blank\">completeness<\/a>, it is important to include a counterion. And because the colour mauve is recorded in methanol solutions (<em>i.e.<\/em> it is unlikely to be due to aggregation), we will include some explicit solvent (water) as well. To illustrate the model, I show the geometries calculated for two counter-ion isomers of tautomer <strong>4<\/strong> using \u03c9B97XD\/6-311G(d,p)\/SCRF=water.<\/p>\n<table border=\"1\">\n<tbody>\n<tr>\n<td><div id=\"attachment_5256\" style=\"width: 209px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-5256\" class=\"size-full wp-image-5256  \" title=\"tauomer4\" onclick=\"jmolInitialize('..\/Jmol\/',true);jmolSetAppletColor('white');jmolApplet([600,600],'load wp-content\/uploads\/2011\/10\/4.xml;');\" src=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/10\/tauomer4.jpg\" alt=\"\" width=\"199\" height=\"106\" \/><p id=\"caption-attachment-5256\" class=\"wp-caption-text\">Tautomer 4. Click for 3D.<\/p><\/div><\/td>\n<td><div id=\"attachment_5257\" style=\"width: 209px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-5257\" class=\"size-full wp-image-5257  \" title=\"tauomer5\" onclick=\"jmolInitialize('..\/Jmol\/',true);jmolSetAppletColor('white');jmolApplet([600,600],'load wp-content\/uploads\/2011\/10\/5.xml;');\" src=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/10\/tauomer5.jpg\" alt=\"\" width=\"199\" height=\"107\" \/><p id=\"caption-attachment-5257\" class=\"wp-caption-text\">Tautomer 4, with different arrangement of Chloride. Click for 3D.<\/p><\/div><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p>The predicted UV\/Visible spectra are shown below (\u03c9B97XD\/6-311++G(d,p)\/SCRF=water model), and \u00a0\u03bb<sub>max<\/sub>\u00a0ranges from 440 to 655nm simply by moving one proton around! The spectrum that matches the measured best corresponds to tautomer <strong>4<\/strong>. Unfortunately, it is calculated to be about 15 kcal\/mol higher in energy than tautomer <strong>1<\/strong>, which is the lowest in energy.<\/p>\n<table border=\"1\">\n<tbody>\n<tr>\n<th><a href=\"http:\/\/hdl.handle.net\/10042\/to-9645\" target=\"_blank\">\u03bb<sub>max 440<\/sub><\/a><\/th>\n<th><a href=\"http:\/\/hdl.handle.net\/10042\/to-9648\" target=\"_blank\">\u03bb<sub>max 655<\/sub><\/a><\/th>\n<\/tr>\n<tr>\n<td><img decoding=\"async\" class=\"aligncenter\" src=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/10\/M1.svg\" alt=\"colour table\" width=\"200\" \/><\/td>\n<td><img decoding=\"async\" class=\"aligncenter\" src=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/10\/M2.svg\" alt=\"colour table\" width=\"200\" \/><\/td>\n<\/tr>\n<tr>\n<th>\u03bb<sub>max 555<\/sub><\/th>\n<th><a href=\"http:\/\/hdl.handle.net\/10042\/to-9646\" target=\"_blank\">\u03bb<sub>max 490<\/sub><\/a><\/th>\n<\/tr>\n<tr>\n<td><img decoding=\"async\" class=\"aligncenter\" src=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/10\/M3.svg\" alt=\"colour table\" width=\"200\" \/><\/td>\n<td><img decoding=\"async\" class=\"aligncenter\" src=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/10\/M4.svg\" alt=\"colour table\" width=\"200\" \/><\/td>\n<\/tr>\n<tr>\n<th colspan=\"2\"><a href=\"http:\/\/hdl.handle.net\/10042\/to-9647\" target=\"_blank\">\u03bb<sub>max 487<\/sub><\/a><\/th>\n<\/tr>\n<tr>\n<td colspan=\"2\"><img decoding=\"async\" class=\"aligncenter\" src=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/10\/M5.svg\" alt=\"colour table\" width=\"400\" \/><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p>So one step forward, and one back. A better colour match can be obtained by modelling a different tautomer of mauveine, but this now leaves the energy unexplained. I think perhaps a determined effort to get mauveine itself to form good crystals and to analyse those to confirm where the three exchangeable hydrogens reside would be well worth the effort. Even then, that will not necessarily tell us what is happening in solution. Such an old, and famous molecule, and still there is a mystery.<\/p>\n<!-- kcite active, but no citations found -->\n<\/div> <!-- kcite-section 5248 -->","protected":false},"excerpt":{"rendered":"<p>My previous post on the topic of mauveine left the outcome dangling.\u00a0Put simply, \u03bbmax is measured at about 549nm for mauveine A, but was calculated at about 440nm using a modern method for predicting colour (TD-DFT). According to the colour table below, that would make it orange, not mauve. Can the theoretical prediction be out [&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":[],"tags":[715,24,714,2651,413,713],"ppma_author":[2661],"class_list":["post-5248","post","type-post","status-publish","format-standard","hentry","tag-and-one-back","tag-energy","tag-forward","tag-historical","tag-mauveine","tag-methanol-solutions"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.6 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>The colour of purple is ... not orange but mauve? - 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=5248\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"The colour of purple is ... not orange but mauve? - Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"og:description\" content=\"My previous post on the topic of mauveine left the outcome dangling.\u00a0Put simply, \u03bbmax is measured at about 549nm for mauveine A, but was calculated at about 440nm using a modern method for predicting colour (TD-DFT). 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Can the theoretical prediction be out [&hellip;]","og_url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=5248","og_site_name":"Henry Rzepa&#039;s Blog","article_published_time":"2011-10-26T15:14:08+00:00","article_modified_time":"2011-10-27T07:41:22+00:00","og_image":[{"url":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/03\/colour-table.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=5248#article","isPartOf":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=5248"},"author":{"name":"Henry Rzepa","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/#\/schema\/person\/2b40f7b9c872a4dc1547e040a11b6281"},"headline":"The colour of purple is &#8230; not orange but mauve?","datePublished":"2011-10-26T15:14:08+00:00","dateModified":"2011-10-27T07:41:22+00:00","mainEntityOfPage":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=5248"},"wordCount":375,"commentCount":4,"image":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=5248#primaryimage"},"thumbnailUrl":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/03\/colour-table.jpg","keywords":["and one back","energy","forward","Historical","Mauveine","methanol solutions"],"inLanguage":"en-GB","potentialAction":[{"@type":"CommentAction","name":"Comment","target":["https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=5248#respond"]}]},{"@type":"WebPage","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=5248","url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=5248","name":"The colour of purple is ... not orange but mauve? 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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":20333,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=20333","url_meta":{"origin":5248,"position":1},"title":"The history of  Alizarin (and madder).","author":"Henry Rzepa","date":"October 18, 2018","format":false,"excerpt":"The Royal Society of Chemistry historical group (of which I am a member) organises two or three one day meetings a year. Yesterday the October meeting covered (amongst other themes) the fascinating history of madder and its approximately synthetic equivalent alizarin. Here I add a little to the talk given\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":[]},{"id":17376,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=17376","url_meta":{"origin":5248,"position":2},"title":"Revisiting (and maintaining) a twenty year old web page. Mauveine: The First Industrial Organic Fine-Chemical.","author":"Henry Rzepa","date":"February 2, 2017","format":false,"excerpt":"Almost exactly 20 years ago, I started what can be regarded as the precursor to this blog. As part of a celebration of this anniversary, I revisited the page to see whether any of it had withstood the test of time. Here I recount what I discovered. The site itself\u2026","rel":"","context":"In &quot;Chemical IT&quot;","block_context":{"text":"Chemical IT","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=2"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/02\/038-1024x419.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":3723,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=3723","url_meta":{"origin":5248,"position":3},"title":"Chemicalizing a blog.","author":"Henry Rzepa","date":"March 30, 2011","format":false,"excerpt":"I am at the ACS meeting, attending a session on chemistry and the Internet. This post was inspired by Chemicalize, a service offered by ChemAxon, which scans a post like this one, and identifies molecules named. I had previously used generic post taggers, which frankly did not work well in\u2026","rel":"","context":"In &quot;Chemical IT&quot;","block_context":{"text":"Chemical IT","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=2"},"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":5248,"position":4},"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":25827,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=25827","url_meta":{"origin":5248,"position":5},"title":"A look at (one of) the dyes used in the  Bayeaux tapestry.","author":"Henry Rzepa","date":"January 3, 2023","format":false,"excerpt":"I have previously looked at the pigments used to colour the Book of Kells, which dates from around 800 AD and which contained arsenic sulfide as the yellow colourant. The Bayeaux tapestry is a later embroidery dating probably from around 1077 and here the colours are based entirely on mordanted\u2026","rel":"","context":"Similar post","block_context":{"text":"Similar post","link":""},"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\/5248","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=5248"}],"version-history":[{"count":0,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/5248\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=5248"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=5248"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=5248"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=5248"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}