{"id":11597,"date":"2013-11-10T13:19:45","date_gmt":"2013-11-10T13:19:45","guid":{"rendered":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=11597"},"modified":"2014-07-19T17:06:33","modified_gmt":"2014-07-19T16:06:33","slug":"the-subtle-effect-of-dispersion-forces-on-the-shapes-of-molecules-benzyl-magnesium-bromide","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=11597","title":{"rendered":"The subtle effect of dispersion forces on the shapes of molecules: benzyl magnesium bromide."},"content":{"rendered":"
\n

In the previous post<\/a> I mentioned in passing the Grignard reagent benzyl magnesium bromide as having tetrahedral coordination at Mg. But I have now noticed, largely through spotting Steve Bachrach’s post on “Acene dimers \u2013 open or closed<\/a>?” another geometric effect perhaps worthy of note, certainly one not always noted in the past; that of dispersion forces.<\/p>\n\n\n\n\n
crystal structure<\/th>\nCalc structure<\/th>\n<\/tr>\n
\n
\"Click

Click for 3D<\/p><\/div>\n<\/td>\n

\n
\"Click

Click for 3D<\/p><\/div>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

On the left is the crystal structure.[1]<\/a><\/span> and on the right a\u00a0\u03c9B97Xd\/6-311G(d,p) calculation, with built-in dispersion correction. If you compare the two you will find that the ethyl groups from the ether are about 0.3\u00c5 closer to the face of the phenyl group in the calculated structure. Why? Well, in the crystal structure, each dimeric Grignard unit is surrounded by adjacent units in the periodic lattice. You would think that this would have the effect of compressing the structure. Instead it is more open, and it is the isolated calculated structure that is compressed. The dispersion forces are responsible for this. In the crystal structure, the phenyl group is attracted not only to the ethyl groups but also by adjacent units in the lattice by dispersion forces. This balancing effect is absent in the calculated structure and so manifests as just an attraction between the phenyl face and the methyl groups, which pulls them together by ~0.3\u00c5. One can see this more clearly when an NCI <\/a>(non-covalent-interactions) isosurface is shown at both geometries:<\/p>\n\n\n\n\n
X-ray geometry[2]<\/a><\/span><\/th>\nCalc. geometry [3]<\/a><\/span><\/th>\n<\/tr>\n
\n
\"Click

Click for 3D<\/p><\/div>\n<\/td>\n

\n
\"Click

Click for 3D<\/p><\/div>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

The surface on the right is ringed (red) in the relevant region to show how the green NCI surface is so much larger compared to the one computed for the \u00a0crystal structure. Notice by the way the strong stabilizing (blue) zone between the two Mg atoms. Whether it should be called metal-metal bonding is another issue, but it is a clear effect.<\/p>\n

One can compare this result with NCI surfaces<\/a> computed for the examples described in Steve’s blog (deriving from this article[4]<\/a><\/span>). There two geometric isomers of the same molecule were described, differing only in the dispersion attractions. The top one is an open form and the NCI surface shows no features along the acene chain away from the central pivot. The second isomer shows stabilizing green regions (indicating a zone of dispersion forces in action) between the extended acene groups.<\/p>\n\n\n\n\n
Open<\/th>\nClosed<\/th>\n<\/tr>\n
\n
\"Click

Click for 3D. Open acene<\/p><\/div>\n<\/td>\n

\n
\"Click

Click for 3D. Closed acene with more green regions.<\/p><\/div>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Whilst the acene system is an extreme example of this sort of effect, it may well be that even quite small molecules such as benzyl magnesium bromide etherate might manifest effects due to dispersion. After all, 0.3\u00c5 is not a particularly small change in geometry! I conclude by noting that isopropyl groups are rather better in their attraction to a phenyl ring than ethyl groups, and so one might speculate whether e.g.<\/em> the di-isopropyl etherate of benzyl magnesium bromide might be worth\u00a0someone making?<\/p>\n

References<\/h2>\n
  1. M.A. Nesbit, D.L. Gray, and G.S. Girolami, \"Di-\u03bc-bromido-bis[benzyl(diethyl ether)magnesium]\", Acta Crystallographica Section E Structure Reports Online<\/i>, vol. 68, pp. m942-m942, 2012. https:\/\/doi.org\/10.1107\/s1600536812025445<\/a>\n\n<\/li>\n
  2. S. Ehrlich, H.F. Bettinger, and S. Grimme, \"Dispersion\u2010Driven Conformational Isomerism in \u03c3\u2010Bonded Dimers of Larger Acenes\", Angewandte Chemie International Edition<\/i>, vol. 52, pp. 10892-10895, 2013. https:\/\/doi.org\/10.1002\/anie.201304674<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> ","protected":false},"excerpt":{"rendered":"

    In the previous post I mentioned in passing the Grignard reagent benzyl magnesium bromide as having tetrahedral coordination at Mg. But I have now noticed, largely through spotting Steve Bachrach’s post on “Acene dimers \u2013 open or closed?” another geometric effect perhaps worthy of note, certainly one not always noted in the past; that of […]<\/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":[1096,20,42],"ppma_author":[2661],"class_list":["post-11597","post","type-post","status-publish","format-standard","hentry","category-interesting-chemistry","tag-metal-metal-bonding","tag-steve-bachrach","tag-x-ray"],"yoast_head":"\nThe subtle effect of dispersion forces on the shapes of molecules: benzyl magnesium bromide. - 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=11597\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"The subtle effect of dispersion forces on the shapes of molecules: benzyl magnesium bromide. - Henry Rzepa's Blog\" \/>\n<meta property=\"og:description\" content=\"In the previous post I mentioned in passing the Grignard reagent benzyl magnesium bromide as having tetrahedral coordination at Mg. 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Q: \"Show curly arrows for the formation of the product of the following reaction, together with a Lewis representation of that product: Et2O + MgBr2\". A:\u00a0Et2O+-Mg-Br2 (a product by the way that is known as\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\/11\/TOQKIT.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":4002,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=4002","url_meta":{"origin":11597,"position":1},"title":"The Sn1…Sn2 mechanistic continuum. The special case of neopentyl bromide","author":"Henry Rzepa","date":"May 9, 2011","format":false,"excerpt":"Introductory organic chemistry invariably features the mechanism of haloalkane solvolysis, and introduces both the Sn1 two-step mechanism, and the Sn2 one step mechanism to students. They are taught to balance electronic effects (the stabilization of carbocations) against steric effects in order to predict which mechanism prevails. It was whilst preparing\u2026","rel":"","context":"In \"free energy\"","block_context":{"text":"free energy","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?tag=free-energy"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/05\/neopentyl-ts.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":23281,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=23281","url_meta":{"origin":11597,"position":2},"title":"The Stevens rearrangement: how history gives us new insights.","author":"Henry Rzepa","date":"January 29, 2021","format":false,"excerpt":"In a recent post, I told the story of how in the early 1960s, Robert Woodward had encountered an unexpected stereochemical outcome to the reaction of a hexatriene, part of his grand synthesis of vitamin B12. He had constructed a model of the reaction he wanted to undertake, perhaps with\u2026","rel":"","context":"In "Historical"","block_context":{"text":"Historical","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=565"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2021\/01\/sden.jpg?resize=350%2C200&ssl=1","width":350,"height":200},"classes":[]},{"id":22656,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=22656","url_meta":{"origin":11597,"position":3},"title":"High-performance polythioesters with high chemical recyclability.","author":"Henry Rzepa","date":"September 2, 2020","format":false,"excerpt":"Here I investigate a recent report of a new generation of polyesters with the intrinsic properties of high crystallinity and chemical recyclability. The latter point is key, since many current plastics cannot be easily recycled to a form which can be used to regenerate the original polymer with high yield.\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\/2020\/09\/RSSR-lit-1024x759.jpg?resize=350%2C200&ssl=1","width":350,"height":200},"classes":[]},{"id":7420,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=7420","url_meta":{"origin":11597,"position":4},"title":"Curly arrow pushing: another reality check.","author":"Henry Rzepa","date":"August 5, 2012","format":false,"excerpt":"Two years ago, I discussed how curly arrow pushing is taught, presenting four different ways of showing the arrows.\u00a0One of the comments posted to that blog suggested that all of the schemes shown below were deficient in one aspect. The issues were the stereo and regiochemistry. In particular, the diagram\u2026","rel":"","context":"In "Curly arrows"","block_context":{"text":"Curly arrows","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=2327"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2010\/10\/arrow_pushing.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":25521,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=25521","url_meta":{"origin":11597,"position":5},"title":"Why does octafluorocubane have such a high sublimation point?","author":"Henry Rzepa","date":"September 8, 2022","format":false,"excerpt":"The recently reported synthesis of octafluorocubane established a sublimation point as 168.1\u2013177.1\u00b0C (a melting point was not observed). In contrast, the heavier perfluoro-octane has an m.p. of -25\u00b0C. Why the difference? Firstly, the crystal structure is shown below, albeit as a dimer rather than a periodic lattice (click on image\u2026","rel":"","context":"With 2 comments","block_context":{"text":"With 2 comments","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=25521#comments"},"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\/11597","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=11597"}],"version-history":[{"count":28,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/11597\/revisions"}],"predecessor-version":[{"id":12756,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/11597\/revisions\/12756"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=11597"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=11597"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=11597"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=11597"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}