{"id":24974,"date":"2022-04-07T13:41:18","date_gmt":"2022-04-07T12:41:18","guid":{"rendered":"https:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=24974"},"modified":"2022-04-07T16:23:31","modified_gmt":"2022-04-07T15:23:31","slug":"b2n2-a-10-electron-four-atom-molecule-displaying-both-huckel-4n2-and-baird-4n-selection-rules-for-ring-aromaticity","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=24974","title":{"rendered":"C2N2: a 10-electron four-atom molecule displaying both H\u00fcckel 4n+2 and Baird 4n selection rules for ring aromaticity."},"content":{"rendered":"
\n

The previous examples<\/a> of four atom systems displaying two layers of aromaticity illustrated how 4 (B4<\/sub>), 8 (C4<\/sub>) and 12 (N4<\/sub>) valence electrons were partitioned into 4n+2 manifolds (respectively 2+2, 6+2 and 6+6). The triplet state molecule B2<\/sub>C2<\/sub> with 6 electrons partitioned into 2\u03c0 and 4\u03c3 electrons, with the latter following Baird’s aromaticity rule.[1]<\/a><\/span>,[2]<\/a><\/span>. Now for the final missing entry; as a triplet C2<\/sub>N2<\/sub> has 10 electrons, which now partition into 4 + 6. But would that be 4\u03c0 + 6\u03c3 or 4\u03c3 + 6\u03c0? Well, in a way neither! Read on.<\/p>\n

\"\"<\/a><\/p>\n\n\n\n\n\n\n\n\n\n
Bonding MOs for C2<\/sub>N2<\/sub>.
\nClick image to load 3D model<\/th>\n<\/tr>\n
π3, 1 electron<\/th>\nπ2, 1 electron<\/th>\n<\/tr>\n
\"\"<\/td>\n\"\"<\/td>\n<\/tr>\n
\u03c33 2 electron<\/th>\nσ2, 2 electron<\/th>\n<\/tr>\n
\"\"<\/td>\n\"\"<\/td>\n<\/tr>\n
π1 2 electron<\/th>\nσ1, 2 electron<\/th>\n<\/tr>\n
\"\"<\/td>\n\"\"<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

The calculations (\u03c9B97XD\/Def2-TZVPP and CCSD(T)\/Def2-TZVPP) are collected at FAIR DOI: 10.14469\/hpc\/10346<\/a>. These show a partitioning into\u00a05\u03c3 + 5\u03c0, a species that is not a minimum but undergoes a non-planar distortion.
\n\"\"<\/a>\n<\/p>\n

However, the first excited state (the triplet)\u00a0IS planar and is only 12.5 kcal\/mol above the planar 5+5 precursor.\u00a0It is now partitioned into\u00a06\u03c3 and 4\u03c0, with the latter conforming to Baird’s rule for open shell triplets.[1]<\/a><\/span>,[2]<\/a><\/span>\u00a0So this is unlike C2<\/sub>B2<\/sub>, which showed\u00a02\u03c0 + 4\u03c3 partitioning with the \u03c3 series following Baird’s rule. Now we have two examples in which one of the \u03c3 or the \u03c0-manifolds follow Baird’s rule and the other follows H\u00fcckel’s rule. The systems themselves are somewhat contrived, but they show the simple fun and games that can be had with these aromaticity rules.<\/p>\n

\n

This post has DOI: 10.14469\/hpc\/10350<\/a><\/p>\n

References<\/h2>\n
  1. N.C. Baird, \"Quantum organic photochemistry. II. Resonance and aromaticity in the lowest 3.pi..pi.* state of cyclic hydrocarbons\", Journal of the American Chemical Society<\/i>, vol. 94, pp. 4941-4948, 1972. https:\/\/doi.org\/10.1021\/ja00769a025<\/a>\n\n<\/li>\n
  2. M. Rosenberg, C. Dahlstrand, K. Kils\u00e5, and H. Ottosson, \"Excited State Aromaticity and Antiaromaticity: Opportunities for Photophysical and Photochemical Rationalizations\", Chemical Reviews<\/i>, vol. 114, pp. 5379-5425, 2014. https:\/\/doi.org\/10.1021\/cr300471v<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> ","protected":false},"excerpt":{"rendered":"

    The previous examples of four atom systems displaying two layers of aromaticity illustrated how 4 (B4), 8 (C4) and 12 (N4) valence electrons were partitioned into 4n+2 manifolds (respectively 2+2, 6+2 and 6+6). The triplet state molecule B2C2 with 6 electrons partitioned into 2\u03c0 and 4\u03c3 electrons, with the latter following Baird’s aromaticity rule.,. Now […]<\/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_feature_clip_id":0,"_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},"jetpack_post_was_ever_published":false},"categories":[4],"tags":[],"ppma_author":[2661],"class_list":["post-24974","post","type-post","status-publish","format-standard","hentry","category-interesting-chemistry"],"yoast_head":"\nC2N2: a 10-electron four-atom molecule displaying both H\u00fcckel 4n+2 and Baird 4n selection rules for ring aromaticity. - 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=24974\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"C2N2: a 10-electron four-atom molecule displaying both H\u00fcckel 4n+2 and Baird 4n selection rules for ring aromaticity. - Henry Rzepa's Blog\" \/>\n<meta property=\"og:description\" content=\"The previous examples of four atom systems displaying two layers of aromaticity illustrated how 4 (B4), 8 (C4) and 12 (N4) valence electrons were partitioned into 4n+2 manifolds (respectively 2+2, 6+2 and 6+6). The triplet state molecule B2C2 with 6 electrons partitioned into 2\u03c0 and 4\u03c3 electrons, with the latter following Baird’s aromaticity rule.,. 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The triplet state molecule B2C2 with 6 electrons partitioned into 2\u03c0 and 4\u03c3 electrons, with the latter following Baird’s aromaticity rule.,. 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The best known is the H\u00fcckel 4n+2 rule (n=0,1, etc) for inferring diatropic aromatic ring currents in singlet-state \u03c0-conjugated cyclic molecules\u2021 and a counter 4n rule which infers an antiaromatic paratropic ring current for the system.\u2026","rel":"","context":"In "Interesting chemistry"","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\/2022\/03\/C2B2-300x212.jpg?resize=350%2C200&ssl=1","width":350,"height":200},"classes":[]},{"id":24769,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=24769","url_meta":{"origin":24974,"position":1},"title":"An unusually small (doubly) aromatic molecule: C4.","author":"Henry Rzepa","date":"March 15, 2022","format":false,"excerpt":"When you talk \u03c0-aromaticity, benzene is the first molecule that springs to mind.\u00a0But there are smaller molecules that can carry this property; cyclopropenylidene (five atoms) is the smallest in terms of atom count I could think of until now, apart that is from H3+ which is the smallest possible molecule\u2026","rel":"","context":"In "General"","block_context":{"text":"General","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=1"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]},{"id":22996,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=22996","url_meta":{"origin":24974,"position":2},"title":"An interesting aromatic molecule found in Titan’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 "Interesting chemistry"","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":24503,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=24503","url_meta":{"origin":24974,"position":3},"title":"Molecule of the year 2021: Infinitene.","author":"Henry Rzepa","date":"December 16, 2021","format":false,"excerpt":"The annual \"molecule of the year\" results for 2021 are now available ... and the winner is Infinitene., This is a benzocirculene in the form of a figure eight loop (the infinity symbol), a shape which is also called a lemniscate after the mathematical (2D) function due to Bernoulli. The\u2026","rel":"","context":"In "Chiroptics"","block_context":{"text":"Chiroptics","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=2644"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2021\/12\/infinitene.jpg?resize=350%2C200&ssl=1","width":350,"height":200},"classes":[]},{"id":9556,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=9556","url_meta":{"origin":24974,"position":4},"title":"Linking numbers, and twist and writhe components for two extended porphyrins.","author":"Henry Rzepa","date":"February 17, 2013","format":false,"excerpt":"My last comment as\u00a0appended to the previous post\u00a0promised to analyse two so-called extended porphyrins for their topological descriptors. I start with the\u00a0C\u00e3lug\u00e3reanu\/Fuller theorem\u00a0 which decomposes the topology of a space curve into two components, its twist (Tw) and its writhe (Wr, this latter being the extent to which coiling of\u2026","rel":"","context":"In "Interesting chemistry"","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":11421,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=11421","url_meta":{"origin":24974,"position":5},"title":"Six vs ten aromatic electrons?","author":"Henry Rzepa","date":"October 20, 2013","format":false,"excerpt":"Homoaromaticity is a special case of\u00a0aromaticity\u00a0in which\u00a0\u03c0-conjugation\u00a0is interrupted by a single sp3\u00a0hybridized\u00a0carbon atom (it is sometimes referred to as a suspended \u03c0-bond with no underlying \u03c3-foundation).\u00a0But consider the carbene shown below. This example comes from a recently published article which was highlighted on Steve Bachrach's blog. Here aromaticity has resulted\u2026","rel":"","context":"In "Interesting chemistry"","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\/10\/B10-sigma.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","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\/24974","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=24974"}],"version-history":[{"count":36,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/24974\/revisions"}],"predecessor-version":[{"id":25040,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/24974\/revisions\/25040"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=24974"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=24974"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=24974"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=24974"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}