{"id":17311,"date":"2016-12-31T12:43:17","date_gmt":"2016-12-31T12:43:17","guid":{"rendered":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=17311"},"modified":"2022-07-28T12:23:25","modified_gmt":"2022-07-28T11:23:25","slug":"the-hydrogen-bond-its-early-history","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=17311","title":{"rendered":"The “hydrogen bond”; its early history."},"content":{"rendered":"
\n

My holiday reading has been Derek Lowe’s excellent\u00a0Chemistry Book<\/strong><\/em> setting out 250 milestones in chemistry, organised by year. An\u00a0entry for 1920 entitled hydrogen bonding<\/em>\u00a0seemed worth exploring in more detail here.<\/p>\n

As with many historical concepts, it can often take a few years to coalesce into something we would readily recognise today, and hydrogen bonds are no exception. Wikipedia is another source of the history and it cites a 1912 article as the origin of the term in relation to the solvation of amines[1]<\/a><\/span> but also notes that the better known setting of water occurs later in 1920.[2]<\/a><\/span> Here I try to capture the essence of the concept with a few diagrams taken from these two articles.<\/p>\n

\u00a0Firstly “The state of amines in aqueous solution<\/em>“[1]<\/a><\/span> which is mostly concerned with the measurement of ionization constants of primary, secondary and tertiary amines. It boils down to the below:<\/p>\n

\"\"<\/p>\n

\"\"<\/p>\n

and the connection to ionization is laid out as:<\/p>\n

\"\"<\/p>\n

\"\"<\/p>\n

Since in 1912, Lewis’ electron pair theory of the covalent bond had not yet emerged, the authors use the terms “strong union” and “weak union”, and of course it is the “weak union<\/span><\/strong>” that we now know of as the hydrogen bond<\/span><\/strong>. Some other comments about this seminal diagram:<\/p>\n

    \n
  1. The\u00a0article contains the very explicit and modern term stereochemical, <\/em>which is used in a manner that suggests it was already common.\u2021<\/sup> But there is only a hint\u00a0at most\u00a0that the nitrogen atoms might be tetrahedral, or that the “weak union” between (what we now think of as the lone pair on) the nitrogen and the hydrogen of the water is directional.<\/li>\n
  2. The second weak union between the tetramethyl ammonium (which we now describe as a cation) and the hydroxide (now described as an anion; both terms are\u00a0however\u00a0implied by the description strong electrolyte) is probably not what we would now call a hydrogen bond, more an intimate ion-pair.<\/li>\n<\/ol>\n

    The second article in 1920 on water itself[2]<\/a><\/span> is post-Lewis, but perhaps applied in a manner which we would not entirely agree with nowadays. Thus dinitrogen, N\u2261N is shown as below with just a single connecting bond.<\/p>\n

    \"\"<\/p>\n

    Then we get the interaction\u00a0between ammonia and water,\u2020<\/sup> analogous to the example shown above:<\/p>\n

    \"\"<\/p>\n

    and for water itself:\u2660<\/sup><\/p>\n

    \"\"<\/p>\n

    which in each case shows the central hydrogen having what we now call a valence shell of four<\/strong> electrons,\u2663<\/sup> and hence more equivalent to the “strong unions” above. This shows that in 1920 chemists were rapidly adopting Lewis’ representations, but not always entirely successfully.<\/p>\n

    On balance, I think the 1912 article sets out the modern concept of a hydrogen bond representing a weak union to a hydrogen rather better than the Latimer and Rodebush attempt (at least diagrammatically).<\/p>\n

    \n

    \u2021<\/sup>Stereochemical notation is discussed in this post<\/a>, and it dates from the 1930s.<\/p>\n

    \u2020<\/sup>The modern take is explored here<\/a>, in which the equilibrium set up between a “weak union” between ammonia and water (the weak electrolyte) and\u00a0an isomeric\u00a0“strong union” which represents ionization into an ammonium hydroxide ion-pair (the strong electrolyte) is favoured for the former by \u0394G ~6 kcal\/mol.<\/p>\n

    \u2660<\/sup>The equilibrium between a “weak union” of two water molecules and the fully ionized strong union of hydronium hydroxide favours the former<\/a> by \u0394G ~23 kcal\/mol.<\/p>\n

    \u2663<\/sup>\u00a0This 1920 representation does imply symmetry for the hydrogen, being ~equally disposed between the two oxygens. We now know that such symmetric hydrogen bonding is not unusual (see this post<\/a> for how to fine-tune a hydrogen bond into this situation) but rather than requiring four electrons<\/strong> as implied in the diagram above, it is now better described as a three-centre-two-electron bond<\/strong><\/em> instead.<\/p>\n

    \n

    This post has DOI: 10.14469\/hpc\/10732<\/a><\/p>\n

    \n

    References<\/h2>\n
    1. T.S. Moore, and T.F. Winmill, \"CLXXVII.\u2014The state of amines in aqueous solution\", J. Chem. Soc., Trans.<\/i>, vol. 101, pp. 1635-1676, 1912. https:\/\/doi.org\/10.1039\/ct9120101635<\/a>\n\n<\/li>\n
    2. W.M. Latimer, and W.H. Rodebush, \"POLARITY AND IONIZATION FROM THE STANDPOINT OF THE LEWIS THEORY OF VALENCE.\", Journal of the American Chemical Society<\/i>, vol. 42, pp. 1419-1433, 1920. https:\/\/doi.org\/10.1021\/ja01452a015<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> ","protected":false},"excerpt":{"rendered":"

      My holiday reading has been Derek Lowe’s excellent\u00a0Chemistry Book setting out 250 milestones in chemistry, organised by year. An\u00a0entry for 1920 entitled hydrogen bonding\u00a0seemed worth exploring in more detail here. As with many historical concepts, it can often take a few years to coalesce into something we would readily recognise today, and hydrogen bonds are […]<\/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":[565],"tags":[905,1362,1402,557,1395,1313,1960,1449,1959,1961,1871,1746],"ppma_author":[2661],"class_list":["post-17311","post","type-post","status-publish","format-standard","hentry","category-historical","tag-10-1021","tag-aqueous-solution","tag-chemical-bond","tag-chemical-bonding","tag-chemistry","tag-derek-lowe","tag-hydrogen","tag-hydrogen-bond","tag-intermolecular-forces","tag-lowes","tag-nature","tag-supramolecular-chemistry"],"yoast_head":"\nThe "hydrogen bond"; its early history. - 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=17311\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"The "hydrogen bond"; its early history. - Henry Rzepa's Blog\" \/>\n<meta property=\"og:description\" content=\"My holiday reading has been Derek Lowe’s excellent\u00a0Chemistry Book setting out 250 milestones in chemistry, organised by year. 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In those days the CSD database of crystal structures was a lot smaller (<80,000 structures; it's\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\/SQ-H-pi-1024x783.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":16573,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=16573","url_meta":{"origin":17311,"position":2},"title":"How does an OH or NH group approach an aromatic ring to hydrogen bond with its \u03c0-face?","author":"Henry Rzepa","date":"June 22, 2016","format":false,"excerpt":"I previously used data mining of crystal structures to explore the directing influence of substituents on aromatic and heteroaromatic rings. 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A particularly baffling type of bond is that between the very electronegative F atom and an acid hydrogen atom such as that in OH. Thus short\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\/2019\/03\/F-inter-300x189.png?resize=350%2C200&ssl=1","width":350,"height":200},"classes":[]},{"id":10839,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=10839","url_meta":{"origin":17311,"position":4},"title":"Hexacoordinate hydrogen.","author":"Henry Rzepa","date":"July 8, 2013","format":false,"excerpt":"A feature of a blog which is quite different from a journal article is how rapidly a topic might evolve.\u00a0Thus I started a few days ago with the theme of dicarbon (C2), identifying a metal carbide that showed C2 as a ligand, but which also entrapped a single carbon in\u2026","rel":"","context":"In "Hypervalency"","block_context":{"text":"Hypervalency","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=7"},"img":{"alt_text":"Click for 3D.","src":"https:\/\/i0.wp.com\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/07\/6-H.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":19807,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=19807","url_meta":{"origin":17311,"position":5},"title":"A Theoretical Method for Distinguishing X\u2010H Bond Activation Mechanisms.","author":"Henry Rzepa","date":"July 25, 2018","format":false,"excerpt":"Consider the four reactions. The first two are taught in introductory organic chemistry as (a) a proton transfer,\u00a0often abbreviated PT,\u00a0from X to B (a base) and (b) a hydride transfer from X to A (an acid). The third example is taught as a hydrogen atom transfer or HAT from X\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\/2018\/07\/024-1024x350.jpg?resize=350%2C200&ssl=1","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\/17311","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=17311"}],"version-history":[{"count":12,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/17311\/revisions"}],"predecessor-version":[{"id":25311,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/17311\/revisions\/25311"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=17311"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=17311"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=17311"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=17311"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}