{"id":16987,"date":"2016-10-13T11:37:45","date_gmt":"2016-10-13T10:37:45","guid":{"rendered":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=16987"},"modified":"2016-10-14T06:36:58","modified_gmt":"2016-10-14T05:36:58","slug":"catenated-atoms-and-groups","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=16987","title":{"rendered":"Catenated atoms and groups."},"content":{"rendered":"
\n

Chemists are as fond of records as any, although I doubt you will find many\u00a0chemical ones\u00a0in the Guinness world records<\/a> list. Polytriangulanes chase how many cyclopropyl 3-rings can be joined via<\/em> a vertex. Steve Bachrach on his blog<\/a> reports some recent work by Peter Schreiner and colleagues[1]<\/a><\/span> and the record for catenation of such rings appears to be 15. This led me to think about some other common atoms and groups. Here I have searched for crystal structures only; there may be examples of course for which no such data has been reported.<\/p>\n

    \n
  1. For the halogens F and Cl it is 3.\u00a0<\/li>\n
  2. But for Br,\u00a0believe it or not it reaches the heady value of 24, doi:\u00a010.5517\/CC14K0PD<\/a>[2]<\/a><\/span><\/li>\n
  3. For iodine it is effectively infinite, as noted in my earlier post<\/a>.<\/li>\n
  4. For oxygen it is 3; there are none with four consecutive oxygens.<\/li>\n
  5. For sulfur, a ring of twelve is known[3]<\/a><\/span> and for Se ~11[4]<\/a><\/span><\/li>\n
  6. For nitrogen it may surprise to learn it reaches 6 if the connecting bonds are all single.\u00a0A typical example can be seen at doi:\u00a010.5517\/CCZCR35<\/a>[5]<\/a><\/span> It reaches 10 if any kind of \u00a0N-N bond is allowed. doi:\u00a010.5517\/CCYVNZD<\/a><\/li>\n
  7. For phosphorus, 16 is not uncommon 10.5517\/CC1JWTQY<\/a> [6]<\/a><\/span> but the record may be 21.<\/li>\n
  8. The\u00a0alkyne group C\u2261C, reaches 10 (20 carbon atoms), doi:\u00a010.5517\/CCSGR98<\/a>\u00a0[7]<\/a><\/span><\/li>\n
  9. The carbonyl group\u00a0(C=O) can form a ring of six such groups 10.5517\/CC9JR6R<\/a>[8]<\/a><\/span><\/li>\n<\/ol>\n

    Such records are probably very uncompetitive; I doubt any researchers set out to extend the count. Most of the above are probably simply unexpected discoveries. My favourite is the bromine example; this element so often surprises<\/a>.<\/p>\n

    References<\/h2>\n
    1. W.D. Allen, H. Quanz, and P.R. Schreiner, \"Polytriangulane\", Journal of Chemical Theory and Computation<\/i>, vol. 12, pp. 4707-4716, 2016. https:\/\/doi.org\/10.1021\/acs.jctc.6b00669<\/a>\n\n<\/li>\n
    2. Easton, Max E.., Ward, Antony J.., Hudson, Toby., Turner, Peter., Masters, Anthony F.., and Maschmeyer, Thomas., \"CCDC 1059043: Experimental Crystal Structure Determination\", 2015. https:\/\/doi.org\/10.5517\/cc14k0pd<\/a>\n\n<\/li>\n
    3. J. Steidel, R. Steudel, and A. Kutoglu, \"R\u00f6ntgenstrukturanalysen von Cyclododekaschwefel (S<sub>12<\/sub>) und Cyclododekaschwefel\u20101\u2010Kohlendisulfid (S<sub>12<\/sub> \u00b7 CS<sub>2<\/sub>) [1]\", Zeitschrift f\u00fcr anorganische und allgemeine Chemie<\/i>, vol. 476, pp. 171-178, 1981. https:\/\/doi.org\/10.1002\/zaac.19814760520<\/a>\n\n<\/li>\n
    4. M.G. Kanatzidis, and S.P. Huang, \"Unanticipated redox transformations in gold polyselenides. Isolation and characterization of diselenobis(tetraselenido)diaurate(2-) and undecaselenido(2-)\", Inorganic Chemistry<\/i>, vol. 28, pp. 4667-4669, 1989. https:\/\/doi.org\/10.1021\/ic00325a026<\/a>\n\n<\/li>\n
    5. Klapotke, T.M.., Petermayer, C.., Piercey, D.G.., and Stierstorfer, J.., \"CCDC 905017: Experimental Crystal Structure Determination\", 2013. https:\/\/doi.org\/10.5517\/cczcr35<\/a>\n\n<\/li>\n
    6. Dragulescu-Andrasi, Alina., Miller, L. Zane., Chen, Banghao., McQuade, D. Tyler., and Shatruk, Michael., \"CCDC 1426921: Experimental Crystal Structure Determination\", 2016. https:\/\/doi.org\/10.5517\/cc1jwtqy<\/a>\n\n<\/li>\n
    7. Chalifoux, W.A.., McDonald, R.., Ferguson, M.J.., and Tykwinski, R.R.., \"CCDC 729160: Experimental Crystal Structure Determination\", 2010. https:\/\/doi.org\/10.5517\/ccsgr98<\/a>\n\n<\/li>\n
    8. Abrahams, B.F.., Haywood, M.G.., and Robson, R.., \"CCDC 284214: Experimental Crystal Structure Determination\", 2006. https:\/\/doi.org\/10.5517\/cc9jr6r<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> ","protected":false},"excerpt":{"rendered":"

      Chemists are as fond of records as any, although I doubt you will find many\u00a0chemical ones\u00a0in the Guinness world records list. Polytriangulanes chase how many cyclopropyl 3-rings can be joined via a vertex. Steve Bachrach on his blog reports some recent work by Peter Schreiner and colleagues and the record for catenation of such rings […]<\/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":true,"_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":[1745],"tags":[],"ppma_author":[2661],"class_list":["post-16987","post","type-post","status-publish","format-standard","hentry","category-crystal_structure_mining"],"yoast_head":"\nCatenated atoms and groups. - Henry Rzepa'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=16987\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Catenated atoms and groups. - Henry Rzepa's Blog\" \/>\n<meta property=\"og:description\" content=\"Chemists are as fond of records as any, although I doubt you will find many\u00a0chemical ones\u00a0in the Guinness world records list. 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