{"id":13458,"date":"2015-02-27T19:43:41","date_gmt":"2015-02-27T19:43:41","guid":{"rendered":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=13458"},"modified":"2023-09-16T18:10:46","modified_gmt":"2023-09-16T17:10:46","slug":"how-many-water-molecules-does-it-take-to-ionise-hf-and-hbr","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=13458","title":{"rendered":"How many water molecules does it take to ionise HF and HBr?"},"content":{"rendered":"
\n

No doubt answers to the question posed in the previous post<\/a>\u00a0are already being obtained by experiment. Just in case that does not emerge in the next day or so, I offer a prediction here.<\/p>\n

The methodology is the same as before, and I have not tried to look for new isomeric forms compared with the structures found with HCl. The method as before is DFT-based: \u03c9B97XD\/6-311++G(2d,2p). In the table below, I am recording the halogen-H distance and the distance from the same H to oxygen. You might also observe a more general principle here; first calibrate the method you intend to use with a system where there is an experimental answer. If the two match, use the same method to predict (extrapolate) to systems as yet unmeasured.<\/p>\n\n\n\n\n\n\n\n\n\n\n
<\/th>\nF<\/th>\nCl<\/th>\nBr<\/th>\n<\/tr>\n
n<\/th>\nF-H, \u00c5<\/th>\nH-O<\/th>\nCl-H<\/th>\nH-O<\/th>\nBr-H<\/th>\nH-O<\/th>\n<\/tr>\n
1<\/td>\n0.937<\/td>\n1.702[1]<\/a><\/span><\/td>\n1.300<\/td>\n1.857<\/td>\n1.438<\/td>\n1.912[2]<\/a><\/span><\/td>\n<\/tr>\n
2<\/td>\n0.951<\/td>\n1.631[3]<\/a><\/span><\/td>\n1.322<\/td>\n1.728<\/td>\n1.463<\/td>\n1.754[4]<\/a><\/span><\/td>\n<\/tr>\n
3<\/td>\n0.967<\/td>\n1.532[5]<\/a><\/span><\/td>\n1.351<\/td>\n1.579<\/td>\n1.506<\/td>\n1.554[6]<\/a><\/span><\/td>\n<\/tr>\n
4<\/td>\n0.972<\/td>\n1.504[7]<\/a><\/span><\/td>\n1.387<\/td>\n1.470<\/td>\n2.032<\/td>\n1.028<\/span><\/strong>[8]<\/a><\/span><\/td>\n<\/tr>\n
5<\/td>\n1.043<\/td>\n1.329[9]<\/a><\/span><\/td>\n1.841<\/td>\n1.034<\/span><\/strong><\/td>\n2.039<\/td>\n1.021[10]<\/a><\/span><\/td>\n<\/tr>\n
6<\/td>\n1.067<\/td>\n1.283[11]<\/a><\/span><\/td>\n1.880<\/td>\n1.023<\/td>\n2.073<\/td>\n1.013[12]<\/a><\/span><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

From the bond distances, one notices that “ionisation” is an abrupt discontinuous event, happening for four molecules with HBr, five molecules with HCl and more than six molecules with HF. This nicely parallels the pka values<\/a>: HBr (pKa = -9.0) < HCl (pKa = -6.0) << HF (pKa = +3.1).<\/p>\n

It is good\u00a0to see that\u00a0such a process modelled on the nanoscale using just a few discrete molecules can map onto the macroscopic\u00a0scale of solutions.<\/p>\n

\n

Postscript:<\/strong> If you check on the structures of these systems (click on the pictures in the previous post<\/a>) you will see that the discontinuous ionisation event occurs in a bicyclic system, with the water forming two separate rings. Evidence that this really is the structure of microsolvated species has recently been put forward[13]<\/a><\/span>.<\/p>\n

\"hf5h2o\"<\/a><\/p>\n

\n

Acknowledgments<\/h4>\n

This post has been cross-posted in PDF format at <\/a>https:\/\/doi.org\/10.15200\/winn.142554.47660″ rel=”noopener” target=”_blank”>Authorea.<\/p>\n

References<\/h2>\n
  1. H.S. Rzepa, \"H 3 F 1 O 1\", 2015. https:\/\/doi.org\/10.14469\/ch\/190911<\/a>\n\n<\/li>\n
  2. H.S. Rzepa, \"H 3 Br 1 O 1\", 2015. https:\/\/doi.org\/10.14469\/ch\/190907<\/a>\n\n<\/li>\n
  3. H.S. Rzepa, \"H 5 F 1 O 2\", 2015. https:\/\/doi.org\/10.14469\/ch\/190910<\/a>\n\n<\/li>\n
  4. H.S. Rzepa, \"H 5 Br 1 O 2\", 2015. https:\/\/doi.org\/10.14469\/ch\/190909<\/a>\n\n<\/li>\n
  5. H.S. Rzepa, \"H 7 F 1 O 3\", 2015. https:\/\/doi.org\/10.14469\/ch\/190912<\/a>\n\n<\/li>\n
  6. H.S. Rzepa, \"H 7 Br 1 O 3\", 2015. https:\/\/doi.org\/10.14469\/ch\/190913<\/a>\n\n<\/li>\n
  7. H.S. Rzepa, \"H 9 F 1 O 4\", 2015. https:\/\/doi.org\/10.14469\/ch\/190915<\/a>\n\n<\/li>\n
  8. H.S. Rzepa, \"H 9 Br 1 O 4\", 2015. https:\/\/doi.org\/10.14469\/ch\/190916<\/a>\n\n<\/li>\n
  9. H.S. Rzepa, \"H 11 F 1 O 5\", 2015. https:\/\/doi.org\/10.14469\/ch\/190918<\/a>\n\n<\/li>\n
  10. H.S. Rzepa, \"H 11 Br 1 O 5\", 2015. https:\/\/doi.org\/10.14469\/ch\/190919<\/a>\n\n<\/li>\n
  11. H.S. Rzepa, \"H 13 F 1 O 6\", 2015. https:\/\/doi.org\/10.14469\/ch\/190928<\/a>\n\n<\/li>\n
  12. H.S. Rzepa, \"H 13 Br 1 O 6\", 2015. https:\/\/doi.org\/10.14469\/ch\/190917<\/a>\n\n<\/li>\n
  13. C. P\u00e9rez, J.L. Neill, M.T. Muckle, D.P. Zaleski, I. Pe\u00f1a, J.C. Lopez, J.L. Alonso, and B.H. Pate, \"Water\u2013Water and Water\u2013Solute Interactions in Microsolvated Organic Complexes\", Angewandte Chemie International Edition<\/i>, vol. 54, pp. 979-982, 2014. https:\/\/doi.org\/10.1002\/anie.201409057<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> ","protected":false},"excerpt":{"rendered":"

    No doubt answers to the question posed in the previous post\u00a0are already being obtained by experiment. Just in case that does not emerge in the next day or so, I offer a prediction here. 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J. Corey's article in 1997 (DOI:\u00a010.1016\/S0040-4039(96)02248-4) which probed the origins of conformation restriction in aldehydes. The proposal was of (then) unusual hydrogen bonding between the O=C-H...F-B groups. Here I explore whether the NCI (non-covalent-interaction) method can be used to cast light on this\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.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/05\/RUGYEX-x.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":18632,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=18632","url_meta":{"origin":13458,"position":1},"title":"Dispersion \u201cbonds\u201d not involving just hydrogen: can it work for F…H?","author":"Henry Rzepa","date":"July 18, 2017","format":false,"excerpt":"The effects of loading up lots of dispersion attractions (between t-butyl groups) into a compact molecule has the interesting consequence of allowing two \"non-bonded\" hydrogen atoms to approach to ~1.5\u00c5 of each other, thus creating the appearance of a \"bond\" where one normally would not be found. Can such an\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\/2017\/07\/230-1024x551.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":30746,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=30746","url_meta":{"origin":13458,"position":2},"title":"Quantum crystallography: The structure and C-C bond length alternation of [18]-annulene.","author":"Henry Rzepa","date":"February 13, 2026","format":false,"excerpt":"In my story about one of the molecules of the year, cyclo[48]carbon, I noted that the DFT method used in the literature to model the C-C bond length alternation around the ring (OX B3LYP30) had been re-calibrated against a remeasured crystal structure of C18H18 or [18]-annulene (below) in order 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":"","src":"","width":0,"height":0},"classes":[]},{"id":25521,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=25521","url_meta":{"origin":13458,"position":3},"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":[]},{"id":20576,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=20576","url_meta":{"origin":13458,"position":4},"title":"The shortest known CF…HO hydrogen bond.","author":"Henry Rzepa","date":"March 24, 2019","format":false,"excerpt":"There is a predilection amongst chemists for collecting records; one common theme is the length of particular bonds, either the shortest or the longest. 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":24045,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=24045","url_meta":{"origin":13458,"position":5},"title":"Another very large anomeric effect – with a twist.","author":"Henry Rzepa","date":"July 22, 2021","format":false,"excerpt":"In the earlier post on the topic of anomeric effects, I identified a number of outliers associated with large differences in the lengths of two carbon-oxygen bonds sharing a common carbon atom. Here is another of these outliers (MUZZIS) which shows equally unusual properties. This is an oxyanion (counterion is\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\/2021\/07\/MUZZIS-1024x698.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\/13458","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=13458"}],"version-history":[{"count":37,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/13458\/revisions"}],"predecessor-version":[{"id":26455,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/13458\/revisions\/26455"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=13458"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=13458"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=13458"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=13458"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}