{"id":13645,"date":"2015-03-17T21:40:10","date_gmt":"2015-03-17T21:40:10","guid":{"rendered":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=13645"},"modified":"2015-03-18T11:14:08","modified_gmt":"2015-03-18T11:14:08","slug":"a-5-high-straight-flush-of-water-ionised-acids","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=13645","title":{"rendered":"A 5-high straight flush of water-ionised acids?"},"content":{"rendered":"
\n

I do not play poker,\u2021<\/sup> and so I had to look up a 5-4-3-2<\/strong><\/span>-1(A), which Wikipedia informs me is a 5-high straight flush<\/em>, also apparently known as a steel wheel<\/em>. In previous posts<\/a> \u00a0I have suggested acids which can be ionised by (probably)\u00a05, 4, 3 or \u00a01 discrete water molecules in the gas phase; now to try to track down\u00a0\u00a0a candidate for ionisation by the required\u00a0two<\/strong> water molecules to form\u00a0that straight flush.<\/p>\n

As the counter-anion to quaternary ammonium cations, bis<\/em>(trifluoromethylsulfonyl)imide is a component of some ionic liquids. Its conjugate acid is thought[1]<\/a><\/span>,[2]<\/a><\/span> to protonate on the nitrogen.<\/p>\n

\"Click

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

My first obvious attempt was to place two waters near that N-H to see if it would ionise from that position.[3]<\/a><\/span> The proton remains attached to the nitrogen(-:
\n\"ZURWEO-N\"<\/p>\n

Next, how about re-locating the waters so that they are closer to the sulfonyl oxygens? This time we do have the characteristic hydronium cation forming.[4]<\/a><\/span> However, the free energy of this isomer is +6.7 kcal\/mol\u00a0higher relative to the NH form. So not a\u00a05-high straight flush<\/em> in a strict sense, but it perhaps does give a hint of how one might design the missing card.<\/p>\n

\"Click

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

\n

\u2021<\/sup>Confession time. I did spend many a Wednesday afternoon as an undergraduate playing the card game bridge.<\/p>\n

\n

References<\/h2>\n
  1. \"Structures of bis(fluorosulfonyl)imide HN(SO<sub>2<\/sub>F)<sub>2<\/sub>, bis(trifluoromethylsulfonyl)imide HN(SO<sub>2<\/sub>CF<sub>3<\/sub>)<sub>2<\/sub>, and their potassium salts at 150 K\", Zeitschrift f\u00fcr Kristallographie - Crystalline Materials<\/i>, vol. 213, pp. 217-222, 1998. https:\/\/doi.org\/10.1524\/zkri.1998.213.4.217<\/a>\n\n<\/li>\n
  2. Zak, Z.., and Ruzicka, A.., \"CCDC 119129: Experimental Crystal Structure Determination\", 1999. https:\/\/doi.org\/10.5517\/cc3zyww<\/a>\n\n<\/li>\n
  3. H.S. Rzepa, \"C 2 H 5 F 6 N 1 O 6 S 2\", 2015. https:\/\/doi.org\/10.14469\/ch\/191136<\/a>\n\n<\/li>\n
  4. H.S. Rzepa, \"C 2 H 5 F 6 N 1 O 6 S 2\", 2015. https:\/\/doi.org\/10.14469\/ch\/191137<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> ","protected":false},"excerpt":{"rendered":"

    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 in the gas phase; now […]<\/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":[4],"tags":[40,145,1324],"ppma_author":[2661],"class_list":["post-13645","post","type-post","status-publish","format-standard","hentry","category-interesting-chemistry","tag-free-energy","tag-gas-phase","tag-steel-wheel"],"yoast_head":"\nA 5-high straight flush of water-ionised acids? - 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=13645\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"A 5-high straight flush of water-ionised acids? - Henry Rzepa's Blog\" \/>\n<meta property=\"og:description\" content=\"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 in the gas phase; now […]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=13645\" \/>\n<meta property=\"og:site_name\" content=\"Henry Rzepa's Blog\" \/>\n<meta property=\"article:published_time\" content=\"2015-03-17T21:40:10+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2015-03-18T11:14:08+00:00\" \/>\n<meta property=\"og:image\" content=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2015\/03\/ZURWEO.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=\"1 minute\" \/>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"A 5-high straight flush of water-ionised acids? - 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=13645","og_locale":"en_GB","og_type":"article","og_title":"A 5-high straight flush of water-ionised acids? - Henry Rzepa's Blog","og_description":"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 in the gas phase; now […]","og_url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=13645","og_site_name":"Henry Rzepa's Blog","article_published_time":"2015-03-17T21:40:10+00:00","article_modified_time":"2015-03-18T11:14:08+00:00","og_image":[{"url":"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2015\/03\/ZURWEO.jpg","type":"","width":"","height":""}],"author":"Henry Rzepa","twitter_card":"summary_large_image","twitter_misc":{"Written by":"Henry Rzepa","Estimated reading time":"1 minute"},"schema":{"@context":"https:\/\/schema.org","@graph":[{"@type":"Article","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=13645#article","isPartOf":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=13645"},"author":{"name":"Henry Rzepa","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/#\/schema\/person\/2b40f7b9c872a4dc1547e040a11b6281"},"headline":"A 5-high straight flush of water-ionised acids?","datePublished":"2015-03-17T21:40:10+00:00","dateModified":"2015-03-18T11:14:08+00:00","mainEntityOfPage":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=13645"},"wordCount":255,"commentCount":0,"image":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=13645#primaryimage"},"thumbnailUrl":"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2015\/03\/ZURWEO.jpg","keywords":["free energy","gas phase","steel wheel"],"articleSection":["Interesting chemistry"],"inLanguage":"en-GB","potentialAction":[{"@type":"CommentAction","name":"Comment","target":["https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=13645#respond"]}]},{"@type":"WebPage","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=13645","url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=13645","name":"A 5-high straight flush of water-ionised acids? 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