{"id":16208,"date":"2016-04-15T10:03:45","date_gmt":"2016-04-15T09:03:45","guid":{"rendered":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=16208"},"modified":"2016-06-26T08:28:44","modified_gmt":"2016-06-26T07:28:44","slug":"azane-oxide-a-tautomer-of-hydroxylamine","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=16208","title":{"rendered":"Azane oxide, a tautomer of hydroxylamine."},"content":{"rendered":"
\n

\n\tIn the previous post<\/a> I described how hydronium hydroxide or H3<\/sub>O<\/font>+<\/sup>…HO–<\/sup>, an intermolecular tautomer of water, has recently been observed captured inside an organic cage[1]<\/a><\/span> and how the free-standing species in water can be captured computationally with the help of solvating water bridges. Here I explore azane oxide<\/strong> or H3<\/sub>N+<\/sup>-O–<\/sup><\/span>,‡<\/sup> a tautomer of the better known hydroxylamine (H2<\/sub>N-OH<\/span>).\n<\/p>\n

\n\tThe usual search[2]<\/a><\/span> of the Cambridge structure database reveals only two (related) entries[3]<\/a><\/span>,[4]<\/a><\/span> the second reported in 2015.[5]<\/a><\/span>.\n<\/p>\n

\n\t\"NH3-8\"
\n\t\"NH3-8\"\n<\/p>\n

\n\tNow, location of hydrogen atoms is always a bit tricky, but here we see two species H3<\/sub>N+<\/sup>-OH…–<\/sup>O-+<\/sup>NH3<\/sub> connected by a strong hydrogen bond of 1.54Å (click on the above image to see this packing). However, it is noteworthy that the N-O bonds for each of these species are exactly the same length (1.412Å); one might have imagined that whether the oxygen carries a proton or not would affect its bond length to nitrogen. There is here a strong hint that energetically the azane oxide might be relatively low in energy relative to hydroxylamine and perhaps that the zwitterionic form might be favoured when captured with hydrogen bonds.\n<\/p>\n

\n\tSo certainly time for a computational exploration of this species. I am using the three water bridges as before, each comprised of three water molecules and the ωB97XD\/6-311++G(d,p)\/SCRF=water method. In fact the structure optimises[6]<\/a><\/span> to a delightful propeller-like geometry in which bridges are formed from both two AND three waters across the ion-pair, with overall three-fold C3<\/sub> symmetry (i.e. chiral! Indeed, this species has a predicted optical rotation of 40° at 589nm).\n<\/p>\n

\n\t\"NH3-8\"\n<\/p>\n

\n\tHydroxylamine itself has a less symmetric arrangement of hydrogen bonds[7]<\/a><\/span>, with a free energy in fact very similar (within 1 kcal\/mol) to the ion-pair isomer. Here, a stochastic (statistical) exploration of all the various arrangements of water would be needed to be confident that the lowest energy form had been located. I would note that the N-O bond lengths in the ion-pair and neutral forms are respectively 1.399 and 1.435Å.\n<\/p>\n

\n\t\"NH3-8\"\n<\/p>\n

\n\tCertainly, this very brief computational look at azane oxide<\/strong><\/span> suggests that concentrations of this species in aqueous solutions of hydroxylamine might be appreciable (detectable). Its "trapping" inside a suitably designed cavity must be a realistic possibility (the cavity used to trap hydronium hydroxide probably does not have the correct dimensions for this purpose), as indeed illustrated in the two crystal structures noted above.\n<\/p>\n

\n

\n\t‡<\/sup> I have represented this species in ionic form, but you may find text books showing it in dative form, or H3<\/sub>N→O. My personal inclination is to always prefer the ionic form, if only because it enables connections\/analogies such as the one here to hydronium hydroxide to be more easily made.<\/p>\n

References<\/h2>\n
  1. M. Stapf, W. Seichter, and M. Mazik, \"Unique Hydrogen\u2010Bonded Complex of Hydronium and Hydroxide Ions\", Chemistry \u2013 A European Journal<\/i>, vol. 21, pp. 6350-6354, 2015. https:\/\/doi.org\/10.1002\/chem.201406383<\/a>\n\n<\/li>\n
  2. H. Rzepa, \"Search for Azane oxide\", 2016. https:\/\/doi.org\/10.14469\/hpc\/380<\/a>\n\n<\/li>\n
  3. Fischer, Dennis., Klapotke, Thomas M.., and Stierstorfer, Jorg., \"CCDC 1054611: Experimental Crystal Structure Determination\", 2015. https:\/\/doi.org\/10.5517\/cc14ddqn<\/a>\n\n<\/li>\n
  4. Fischer, D.., Klapotke, T.M.., and Stierstorfer, J.., \"CCDC 827687: Experimental Crystal Structure Determination\", 2012. https:\/\/doi.org\/10.5517\/ccws8lh<\/a>\n\n<\/li>\n
  5. D. Fischer, T.M. Klap\u00f6tke, and J. Stierstorfer, \"1,5\u2010Di(nitramino)tetrazole: High Sensitivity and Superior Explosive Performance\", Angewandte Chemie International Edition<\/i>, vol. 54, pp. 10299-10302, 2015. https:\/\/doi.org\/10.1002\/anie.201502919<\/a>\n\n<\/li>\n
  6. H.S. Rzepa, \"H 21 N 1 O 10\", 2016. https:\/\/doi.org\/10.14469\/ch\/192000<\/a>\n\n<\/li>\n
  7. H.S. Rzepa, \"H 21 N 1 O 10\", 2016. https:\/\/doi.org\/10.14469\/ch\/192001<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> ","protected":false},"excerpt":{"rendered":"

    In the previous post I described how hydronium hydroxide or H3O+…HO–, an intermolecular tautomer of water, has recently been observed captured inside an organic cage and how the free-standing species in water can be captured computationally with the help of solvating water bridges. Here I explore azane oxide or H3N+-O–,‡ a tautomer of the better […]<\/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":[1,4],"tags":[1713,509,1623,1583,40,1412,1449,1801,1710,1836,1835,1590,1715,1834,1802],"ppma_author":[2661],"class_list":["post-16208","post","type-post","status-publish","format-standard","hentry","category-general","category-interesting-chemistry","tag-ammonia","tag-aqueous-solutions","tag-bases","tag-energy-relative","tag-free-energy","tag-functional-groups","tag-hydrogen-bond","tag-hydronium","tag-hydroxides","tag-hydroxyl","tag-hydroxylamine","tag-lowest-energy-form","tag-properties-of-water","tag-reducing-agents","tag-self-ionization-of-water"],"yoast_head":"\nAzane oxide, a tautomer of hydroxylamine. - 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=16208\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Azane oxide, a tautomer of hydroxylamine. - Henry Rzepa's Blog\" \/>\n<meta property=\"og:description\" content=\"In the previous post I described how hydronium hydroxide or H3O+…HO–, an intermolecular tautomer of water, has recently been observed captured inside an organic cage and how the free-standing species in water can be captured computationally with the help of solvating water bridges. Here I explore azane oxide or H3N+-O–,‡ a tautomer of the better […]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=16208\" \/>\n<meta property=\"og:site_name\" content=\"Henry Rzepa's Blog\" \/>\n<meta property=\"article:published_time\" content=\"2016-04-15T09:03:45+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2016-06-26T07:28:44+00:00\" \/>\n<meta property=\"og:image\" content=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/04\/CUPZAQ.jpg\" \/>\n<meta name=\"author\" content=\"Henry Rzepa\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"Henry Rzepa\" \/>\n\t<meta name=\"twitter:label2\" content=\"Estimated reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"2 minutes\" \/>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"Azane oxide, a tautomer of hydroxylamine. - Henry Rzepa's Blog","robots":{"index":"index","follow":"follow","max-snippet":"max-snippet:-1","max-image-preview":"max-image-preview:large","max-video-preview":"max-video-preview:-1"},"canonical":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=16208","og_locale":"en_GB","og_type":"article","og_title":"Azane oxide, a tautomer of hydroxylamine. - Henry Rzepa's Blog","og_description":"In the previous post I described how hydronium hydroxide or H3O+…HO–, an intermolecular tautomer of water, has recently been observed captured inside an organic cage and how the free-standing species in water can be captured computationally with the help of solvating water bridges. 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Thus Derek Lowe highlights Molnupiravir which is shown as a hydroxylamine, the representation originating from the Wikipedia page on the molecule. I like stereocentres more clearly identified using eg R\/S notation and so I went to\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\/2021\/03\/molnupiravir-1024x639.jpg?resize=350%2C200&ssl=1","width":350,"height":200},"classes":[]},{"id":16228,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=16228","url_meta":{"origin":16208,"position":1},"title":"Oxane oxide: a tautomer of hydrogen peroxide.","author":"Henry Rzepa","date":"April 15, 2016","format":false,"excerpt":"If H3N+-O-\u00a0is viable compared with its tautomer H2N-OH when carrying water bridges,\u00a0then why not try\u00a0H2O+-O- vs HO-OH? There are no examples to be found in crystal structures!\u00a0The\u00a0solvated structure of\u00a0H2O+-O-\u00a0is modified directly from that of\u00a0H3N+-O- and the computed (\u03c9B97XD\/6-311++G(d,p)\/SCRF=water) structure is\u00a0shown below. Noteworthy is that the hydrogen bonds at\u00a0the\u00a0O+\u00a0end are\u00a0far stronger\u2026","rel":"","context":"In "General"","block_context":{"text":"General","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=1"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]},{"id":18351,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=18351","url_meta":{"origin":16208,"position":2},"title":"Tautomeric polymorphism.","author":"Henry Rzepa","date":"June 1, 2017","format":false,"excerpt":"Conformational polymorphism occurs when a compound crystallises in two polymorphs differing only in the relative orientations of flexible groups (e.g. Ritonavir). At the Beilstein conference, Ian Bruno mentioned another type; \u00a0tautomeric polymorphism, where a compound can crystallise in two forms differing in the position of acidic protons. Here I explore\u2026","rel":"","context":"In "Chemical IT"","block_context":{"text":"Chemical IT","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=2"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/06\/109-1024x537.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":16118,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=16118","url_meta":{"origin":16208,"position":3},"title":"Hydronium hydroxide: the why of pH 7.","author":"Henry Rzepa","date":"April 14, 2016","format":false,"excerpt":"Ammonium hydroxide (NH4+...OH-) can be characterised quantum mechanically when stabilised by water bridges connecting the ion-pairs. It is a small step from there to hydronium hydroxide, or H3O+...OH-. The measured concentrations [H3O+] \u2261 [OH-]\u00a0give\u00a0rise of course to the well-known\u00a0pH 7 of pure water, and converting this ionization constant to a\u2026","rel":"","context":"In "General"","block_context":{"text":"General","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=1"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]},{"id":10184,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=10184","url_meta":{"origin":16208,"position":4},"title":"Intermediates in oxime formation from hydroxylamine and propanone: now you see them, now you don’t.","author":"Henry Rzepa","date":"April 14, 2013","format":false,"excerpt":"A recent theme here has been to subject to scrutiny well-known mechanisms supposedly involving intermediates. These transients can often involve the creation\/annihilation of charge separation resulting from \u00a0proton transfers, something that a cyclic mechanism can avoid. Here I revisit the formation of an oxime from hydroxylamine and propanone, but with\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":"N-pre","src":"https:\/\/i0.wp.com\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/04\/N-pre.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":13645,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=13645","url_meta":{"origin":16208,"position":5},"title":"A 5-high straight flush of water-ionised acids?","author":"Henry Rzepa","date":"March 17, 2015","format":false,"excerpt":"I do not play poker,\u2021 and so I had to look up a 5-4-3-2-1(A), which Wikipedia informs me is a 5-high straight flush, also apparently known as a steel wheel. In previous posts \u00a0I have suggested acids which can be ionised by (probably)\u00a05, 4, 3 or \u00a01 discrete water molecules\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":[]}],"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\/16208","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=16208"}],"version-history":[{"count":19,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/16208\/revisions"}],"predecessor-version":[{"id":16227,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/16208\/revisions\/16227"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=16208"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=16208"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=16208"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=16208"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}