{"id":26340,"date":"2023-08-29T08:47:40","date_gmt":"2023-08-29T07:47:40","guid":{"rendered":"https:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=26340"},"modified":"2023-09-25T19:46:13","modified_gmt":"2023-09-25T18:46:13","slug":"the-double-headed-curly-arrow-as-used-in-mechanistic-representations","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=26340","title":{"rendered":"The “double-headed” curly arrow as used in mechanistic representations."},"content":{"rendered":"
\n

The schematic representation of a chemical reaction mechanism is often drawn using a palette of arrows connecting or annotating the various molecular structures involved. These can be selected from a chemical arrows palette, taken for this purpose from the commonly used structure drawing program Chemdraw. Explanations of how to apply the individual arrows are not always easy to find however!\u00a0Circled in red are the ones to be discussed here, although most carry fascinating and often subtle meanings!\u2021<\/sup>
\n\"\"<\/p>\n

The most common meaning of the double-headed arrow is probably best illustrated by the scheme below, which involves the addition of a nucleophile to a carbonyl compound, forming a presumed “tetrahedral” intermediate, which is then immediately followed by the eviction of a leaving group – the chloride anion in the example below. The two red arrows show an electron pair firstly moving to the oxygen, and then with the reverse arrow 2<\/strong> back to reform the carbonyl group. This process is called an addition\/elimination mechanism. It is therefore tempting to conflate the two steps into one by instead using a double-headed arrow (3<\/strong>, blue), which if nothing else, saves a little bit of time in the drawing – a useful examination technique!<\/p>\n

\"\"<\/p>\n

Of course, the top scheme (red arrows) is a two-step process, involving a discrete (tetrahedral) intermediate and two transition states. The conflated scheme below it (blue arrows) \u00a0might imply (or not) a single-step process with a single transition state. Since few people who draw such schemes have any information on whether it is a two-step or a single step process, the actual chemical meaning of the double-headed arrow is left implicitly ambiguous, without implying anything about how many discrete steps are involved. However, it is tempting to conclude that the first red arrow (1<\/strong>) reduces the double bond order of the carbonyl group to a single bond, which might therefore be expected to lengthen and the second red arrow (2<\/strong>) reforms the double bond, thus shortening the bond. The two arrows clearly do not move simultaneously. The conflated third arrow (3<\/strong>) leaves the status of the carbonyl bond length changes undefined, or might it mean that it first gets longer and then shorter along the reaction path, depending of course on which moves first!<\/p>\n

Enter computation, where the energy pathway of such a reaction can be computed, along with geometries at each stage. Here I explore three examples\u2020<\/sup> to see what results (\u03c9B97XD\/De2-TZVPP\/SCRF=DCM), FAIR DOI: 10.14469\/hpc\/13171<\/a><\/p>\n

Acetyl chloride + Methanol.<\/h3>\n

\"\"<\/p>\n

This uses a model in which a proton transfer from the methanol to the chloride anion is facilitated by water. This enables (but does not enforce) a continuous concerted process to occur. This emerges from the computed intrinsic reaction coordinate (IRC) as having a low barrier and an exothermic reaction, which agrees with experimental observation. The required proton transfer is part of the concerted process, albeit occurring in a second lower energy stage (IRC ~+1.5).
\n\"\"<\/p>\n

But take a look at how the carbonyl bond length changes along this IRC. It first shortens, and only starts to lengthen as the chloride is evicted. So the carbonyl group actually contracts in length at the transition state, the opposite of what might be inferred by using a double-headed arrow.<\/p>\n

\"\"
\nAlso included is the dipole moment response, which does seem to correspond to the formation of an ionic intermediate!<\/p>\n

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

Acetyl chloride + HF.<\/h3>\n

\"\"
\nHydrogen fluoride as a nucleophile replacing methanol shows a much higher barrier, since it is less good as a nucleophile in this context.
\n\"\"<\/a>
\nAgain, observe the bond length response of the carbonyl group, which is at its shortest at the (single step) transition state.
\n\"\"<\/p>\n

This corresponds to a different interpretation of the double-headed arrow, as per below, but occuring as part of a single concerted process not involving any intermediate.
\n\"\"<\/a>
\nThe dipole moment response is rather different from methanol.<\/p>\n

\"\"<\/p>\n

Acetyl chloride + Methylamine.<\/h3>\n

\"\"<\/p>\n

\"\"<\/p>\n

The energy profile now shows two distinct transition states (IRC ~7 and again at 0.0). The first is a very low energy addition to the carbonyl group with concerted eviction of the chloride anion, which only hydrogen bonds to the water shown. The second stage is the proton transfer from the nitrogen to the water and thence relayed to the chloride anion, for which a transition state at IRC ~0.0 is found.<\/p>\n

\"\"But now observe the bond length response, which shows a distinct maximum around the first transition state (IRC ~7). This is the opposite behaviour to the previous two systems, and now indeed matches the original inferences one might make from the double headed arrow.
\n\"\"<\/p>\n

So we can conclude that there are in fact TWO types of double-headed arrow which could be used in mechanistic representations. The first is when arrow 1<\/strong> is ahead of arrow 2<\/strong> (red), resulting in initial weakening of the carbonyl bond. The second is when arrow 4<\/strong> is ahead of arrow 5<\/strong>, resulting in initial strengthening of the carbonyl bond.<\/p>\n

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

Perhaps to avoid confusion, we really need two different representations of a double-headed arrow to clearly differentiate them! Perhaps a reversal of the direction of the arrowhead? But that does not (yet?) exist in the Chemdraw palette.
\n\"\"<\/p>\n

\n

\u2021<\/sup>This is part of the arcane “knowledge” of chemistry which is often absorbed rather than learnt by students of the subject, but which as a result becomes a language that becomes inscrutable to anyone else! \u2020<\/sup>Another example was noted in the previous post<\/a>.<\/small><\/p>\n\n<\/div> ","protected":false},"excerpt":{"rendered":"

The schematic representation of a chemical reaction mechanism is often drawn using a palette of arrows connecting or annotating the various molecular structures involved. These can be selected from a chemical arrows palette, taken for this purpose from the commonly used structure drawing program Chemdraw. Explanations of how to apply the individual arrows are not […]<\/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":[2327,1086],"tags":[2645],"ppma_author":[2661],"class_list":["post-26340","post","type-post","status-publish","format-standard","hentry","category-curl-arrows","category-reaction-mechanism-2","tag-curly-arrows"],"yoast_head":"\nThe "double-headed" curly arrow as used in mechanistic representations. - 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:\/\/doi.org\/10.59350\/f00wf-5tq46\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"The "double-headed" curly arrow as used in mechanistic representations. - Henry Rzepa's Blog\" \/>\n<meta property=\"og:description\" content=\"The schematic representation of a chemical reaction mechanism is often drawn using a palette of arrows connecting or annotating the various molecular structures involved. 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the so called chemical reaction. It is also used to infer, via valence bond or resonance theory, what the mechanistic implications of that reaction\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":22304,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=22304","url_meta":{"origin":26340,"position":1},"title":"Choreographing a chemical ballet: what happens if you change one of the actors?","author":"Henry Rzepa","date":"May 8, 2020","format":false,"excerpt":"Earlier, I explored the choreography or \"timing\", of what might be described as the curly arrows for a typical taught reaction mechanism, the 1,4-addition of a nucleophile to an unsaturated carbonyl compound (scheme 1). I am now going to explore the consequences of changing one of the actors by adding\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":"","width":0,"height":0},"classes":[]},{"id":7258,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=7258","url_meta":{"origin":26340,"position":2},"title":"The first curly arrows…lead to this?","author":"Henry Rzepa","date":"July 20, 2012","format":false,"excerpt":"Little did I imagine, when I discovered the original example of using curly arrows to express mechanism, that the molecule described there might be rather too anarchic to use in my introductory tutorials on organic chemistry. Why? It simply breaks the (it has to be said to some extent informal)\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.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2012\/07\/NO_dim.gif?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":22445,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=22445","url_meta":{"origin":26340,"position":3},"title":"Curly arrows in the 21st Century. Proton-coupled electron transfers.","author":"Henry Rzepa","date":"June 10, 2020","format":false,"excerpt":"One of the most fascinating and important articles dealing with curly arrows I have seen is that by Klein and Knizia on the topic of C-H bond activations using an iron catalyst. These are so-called high spin systems with unpaired electrons and the mechanism of C-H activation involves both double\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\/2020\/06\/TS.jpg?resize=350%2C200&ssl=1","width":350,"height":200},"classes":[]},{"id":26523,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=26523","url_meta":{"origin":26340,"position":4},"title":"More examples of “double-headed” curly arrows: S and C Nucleophiles attacking acetyl chloride","author":"Henry Rzepa","date":"October 12, 2023","format":false,"excerpt":"In an earlier post on this topic,\u2021 I described how the curly-arrows describing the mechanism of a nucleophilic addition at a carbonyl group choreograph in two distinct ways, as seen in red or blue below. The arrows in red can be described as firstly addition to the carbonyl group to\u2026","rel":"","context":"In \"Interesting chemistry\"","block_context":{"text":"Interesting chemistry","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?tag=interesting-chemistry"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]},{"id":20464,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=20464","url_meta":{"origin":26340,"position":5},"title":"The Graham reaction: Deciding upon a reasonable mechanism and curly arrow representation.","author":"Henry Rzepa","date":"February 18, 2019","format":false,"excerpt":"Students learning organic chemistry are often asked in examinations and tutorials to devise the mechanisms (as represented by curly arrows) for the core corpus of important reactions, with the purpose of learning skills that allow them to go on to improvise mechanisms for new reactions. A common question asked by\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":"","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\/26340","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=26340"}],"version-history":[{"count":51,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/26340\/revisions"}],"predecessor-version":[{"id":26513,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/26340\/revisions\/26513"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=26340"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=26340"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=26340"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=26340"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}