{"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":"2015-03-17T21:40:10","modified_gmt":"2015-03-17T21:40:10","slug":"a-5-high-straight-flush-of-water-ionised-acids","status":"publish","type":"post","link":"https:\/\/www.rzepa.net\/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,"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":[6],"tags":[164,169,1324],"class_list":["post-13645","post","type-post","status-publish","format-standard","hentry","category-interesting-chemistry","tag-free-energy","tag-gas-phase","tag-steel-wheel"],"jetpack_publicize_connections":[],"jetpack_featured_media_url":"","jetpack_sharing_enabled":true,"jetpack_shortlink":"https:\/\/wp.me\/p1gPyz-3y5","jetpack_likes_enabled":true,"_links":{"self":[{"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=\/wp\/v2\/posts\/13645","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcomments&post=13645"}],"version-history":[{"count":0,"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=\/wp\/v2\/posts\/13645\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=13645"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=13645"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=13645"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}