{"id":9424,"date":"2013-02-08T16:39:35","date_gmt":"2013-02-08T16:39:35","guid":{"rendered":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=9424"},"modified":"2023-09-16T19:39:43","modified_gmt":"2023-09-16T18:39:43","slug":"the-conformation-of-acetaldehyde-a-simple-molecule-a-complex-explanation","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=9424","title":{"rendered":"The conformation of acetaldehyde: a simple molecule, a complex explanation?"},"content":{"rendered":"
\n

\n\tConsider acetaldehyde (ethanal for progressive nomenclaturists). What conformation does it adopt, and why? This question was posed of me by a student at the end of a recent lecture of mine. Surely, an easy answer to give? Read on …\n<\/p>\n

\n\t\"acetaldehyde\"<\/a>\n<\/p>\n

\n\tThere really are only two possibilities, the syn<\/strong><\/em> and anti<\/strong><\/em>. Well, I have discovered it is useful to start with a search of the Cambridge data base. With R=H or C, X unspecified,  acyclic and T ≤ 175K, two searches were performed. The first identified the torsion around O=C-C-H. This clearly shows a maximum at 120° (with twice the probability), and a smaller one at 0°. This matches syn<\/strong><\/em>; the anti <\/strong><\/em>conformation above would be expected to have peaks at 60° and 180°; the latter in particular is singularly missing.\n<\/p>\n

\n\t\"acetaldehyde-180\"\n<\/p>\n

\n\tAn alternative search is to define the distance between the oxygen and the H. For the syn<\/strong><\/em> conformer, distances of ~2.5 and 3.1Å are expected; for the anti<\/strong><\/em> conformer, 2.7 and 3.3Å. Again, syn<\/strong><\/em> matches better. Remember, searches based on the position of a hydrogen are less reliable than most, so these distributions provide only a statistical indication.\n<\/p>\n

\n\t\"acetaldehyde-dist\"<\/a>\n<\/p>\n

\n\tNow for a (ωB97XD\/6-311G(d,p) calculation<\/a> of the rotational barrier. The minima occur at torsions of 0, 120 and 240°, matching syn<\/strong><\/em>, although the barrier is very low.\n<\/p>\n

\n\t\"acet-rot\"<\/a>\n<\/p>\n

\n\tNow to try to find explanations. The standard one finds this in three effects:\n<\/p>\n

    \n
  1. \n\t\tDonation from two C-H bonds (R=H above) into the π*C=O<\/sub> NBO orbital (in the manner that was used to explain<\/a> the cis-orientation of the two methyl groups in cis<\/em>-butene). \n\t<\/li>\n
  2. \n\t\tDonation from the single co-planar C-H bond into the σ*C=O<\/sub> NBO orbital (blue bonds above)\n\t<\/li>\n
  3. \n\t\tPauli bond-bond repulsions between two filled NBOs. \n\t<\/li>\n<\/ol>\n

    \n\tEffect 1 has an NBO perturbation energy E(2) of 7.0 kcal\/mol for the syn<\/strong><\/em> conformer and 6.45 for the anti<\/strong><\/em>. The explanation is the π*C=O<\/sub> NBO "leans outward", overlapping better with the C-H bonds in the syn than in the anti<\/strong><\/em>.  the One up to the syn<\/strong><\/em>! Effect 2 has values of 1.3 for the syn<\/strong><\/em> and 4.1 for the anti<\/strong><\/em>. The latter now has the edge. But wait, there are other (smaller) interactions. The syn<\/strong> <\/em>has an antiperiplanar orientation of the two C-H bonds shown above (X=H,red), E(2) = 3.3 vs 0.6 for the corresponding syn-planar orientation in the anti<\/strong><\/em>-conformation. It's now a tie; neck-and-neck.\n<\/p>\n

    \n\tEffect three suggests that the disjoint NLMO steric exchange energy is 54.34 for the anti<\/strong><\/em> and 53.88 (i.e.<\/em> lower) for the syn<\/strong><\/em>. It is vaguely disappointing that no absolutely clear-cut explanation emerges. But then the difference (in total free energy) is only 1.4 kcal\/mol. But even this small difference in energy can manifest in fairly clear-cut conformational preferences obtained from crystal structures. Ultimately of course, all effects in chemistry are reducible to the sum of lots of small effects (in other words unpredictable until one does the sum). \n<\/p>\n

    \n\tI cannot end without mentioning the largest of all the NBO interactions, namely the in-plane lone pair on the oxygen as donor and the aldehyde proton C-H as acceptor (X=H). This has values of 29.3 for syn<\/strong><\/em> and 28.8 kcal\/mol for anti<\/strong><\/em>. This manifest (inter alia<\/em>) in a greatly reduced C-H vibrational wavenumber (ν 2982 for syn<\/strong><\/em>, 2900 cm-1<\/sup> for anti<\/strong><\/em>) compared to the methyl C-H values (~3043-3164).\n<\/p>\n

    \n\tSo this tiny little molecule ended up a little less obvious than might have seemed at the outset. One can find interesting things in even the tiniest of things! \n<\/p>\n

    \n
    \"HC...C-H

    HC…C-H alignment. Click for 3D.<\/p><\/div>\n

    \"HC...C-H

    O=C*…C-H alignment. Click for 3D.<\/p><\/div>\n

    \n

    Acknowledgments<\/h4>\n

    This post has been cross-posted in PDF format at Authorea<\/a>.<\/p>\n\n<\/div> ","protected":false},"excerpt":{"rendered":"

    Consider acetaldehyde (ethanal for progressive nomenclaturists). What conformation does it adopt, and why? This question was posed of me by a student at the end of a recent lecture of mine. Surely, an easy answer to give? Read on … There really are only two possibilities, the syn and anti. Well, I have discovered it is […]<\/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":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":true,"jetpack_social_options":{"image_generator_settings":{"template":"highway","default_image_id":0,"font":"","enabled":false},"version":2}},"categories":[1745,4],"tags":[144,17,24,40,828,373],"ppma_author":[2661],"class_list":["post-9424","post","type-post","status-publish","format-standard","hentry","category-crystal_structure_mining","category-interesting-chemistry","tag-cambridge","tag-conformational-analysis","tag-energy","tag-free-energy","tag-steric-exchange-energy","tag-tutorial-material"],"yoast_head":"\nThe conformation of acetaldehyde: a simple molecule, a complex explanation? - 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=9424\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"The conformation of acetaldehyde: a simple molecule, a complex explanation? - Henry Rzepa's Blog\" \/>\n<meta property=\"og:description\" content=\"Consider acetaldehyde (ethanal for progressive nomenclaturists). 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The components of the search are shown as four queries below, which will be combined in various Boolean senses (DOI:\u00a010.14469\/hpc\/2462). Query one defines the carboxylic acid, with 3-coordinate carbon specified at the\u2026","rel":"","context":"In "crystal_structure_mining"","block_context":{"text":"crystal_structure_mining","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=1745"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/04\/051-1024x676.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":9459,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=9459","url_meta":{"origin":9424,"position":1},"title":"The conformational preference of s-cis amides.","author":"Henry Rzepa","date":"February 10, 2013","format":false,"excerpt":"Amides with an H-N group are a component of the peptide linkage\u00a0(O=C-NH). Here I ask what the conformation (it could also be called a configuration) about the C-N bond is. A search of the following type can be defined: The dihedral shown is for H-N-C=O (but this is equivalent to\u2026","rel":"","context":"In "crystal_structure_mining"","block_context":{"text":"crystal_structure_mining","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=1745"},"img":{"alt_text":"cis-amide","src":"https:\/\/i0.wp.com\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/02\/cis-amide.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":1887,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=1887","url_meta":{"origin":9424,"position":2},"title":"The conformation of 1,2-difluoroethane","author":"Henry Rzepa","date":"April 6, 2010","format":false,"excerpt":"Here I offer another spin-off from writing a lecture course on conformational analysis. This is the famous example of why 1,2-difluoroethane adopts a gauche rather than antiperiplanar conformation. One major contribution to the greater stability of the gauche is the stereoelectronic interactions, and this is best probed using the NBO\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\/2010\/04\/difluoroethane.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":6205,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=6205","url_meta":{"origin":9424,"position":3},"title":"An orbital analysis of the stereochemistry of the E2 elimination reaction","author":"Henry Rzepa","date":"February 4, 2012","format":false,"excerpt":"The so-called E2 elimination mechanism is another one of those mainstays of organic chemistry. It is important because it introduces the principle that anti-periplanarity of the reacting atoms is favoured over other orientations such as the syn-periplanar form; Barton used this principle to great effect in developing the theory 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":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2012\/02\/E2.svg","width":350,"height":200},"classes":[]},{"id":17992,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=17992","url_meta":{"origin":9424,"position":4},"title":"The conformation of enols: revealed and explained.","author":"Henry Rzepa","date":"April 6, 2017","format":false,"excerpt":"Enols are simple compounds with an OH group as a substituent on a C=C double bond and with a very distinct conformational preference for the OH group. Here I take a look at this preference as revealed by crystal structures, with the theoretical explanation. First, a search of the Cambridge\u2026","rel":"","context":"In "crystal_structure_mining"","block_context":{"text":"crystal_structure_mining","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=1745"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/04\/All-1024x948.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":9320,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=9320","url_meta":{"origin":9424,"position":5},"title":"Secrets of a university tutor: conformational analysis and NMR spectroscopy.","author":"Henry Rzepa","date":"February 3, 2013","format":false,"excerpt":"In a previous post, I set out how to show how one can reduce a\u00a01H NMR spectrum to the structure [A] below. I speculated how a further test could be applied to this structure; back predicting its spectrum using just quantum mechanics. Overkill I know, but how well might the\u2026","rel":"","context":"In \"1H NMR\"","block_context":{"text":"1H NMR","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?tag=1h-nmr"},"img":{"alt_text":"C=C-C-S","src":"https:\/\/i0.wp.com\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/02\/CC-C-S.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\/9424","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=9424"}],"version-history":[{"count":28,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/9424\/revisions"}],"predecessor-version":[{"id":26474,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/9424\/revisions\/26474"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=9424"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=9424"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=9424"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=9424"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}