{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T14:27:36Z","timestamp":1786976856634,"version":"build-2736575974"},"reference-count":43,"publisher":"Wiley","issue":"11","license":[{"start":{"date-parts":[[2017,2,23]],"date-time":"2017-02-23T00:00:00Z","timestamp":1487808000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"name":"Fonds der Chemischen Industrie"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2017,3,6]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Herein we present the first superbase\n                    <jats:bold>MHPN<\/jats:bold>\n                    with two interacting P\u2010ylide entities. Unlike classical proton sponges, this novel compound class has carbon atoms as basicity centers which are forced into close proximity by a naphthalene scaffold. The bisylide exhibits an experimental p\n                    <jats:italic>K<\/jats:italic>\n                    <jats:sub>BH<\/jats:sub>\n                    <jats:sup>+<\/jats:sup>\n                    \u2005value of 33.3\u00b10.2 on the MeCN scale and a calculated gas\u2010phase proton affinity of 277.9\u2005kcal\u2009mol\n                    <jats:sup>\u22121<\/jats:sup>\n                    (M062X\/6\u2010311+G**\/\/M062X\/6\u201031G*+ZPVE method) exceeding that of the corresponding monoylide by nearly 15\u2005kcal\u2009mol\n                    <jats:sup>\u22121<\/jats:sup>\n                    . The origin of the unexpectedly high basicity of the new bisylide was investigated by NMR spectroscopic methods, single\u2010crystal X\u2010ray diffraction as well as theoretical calculations and can be partly attributed to the rapid exchange of the \u201cacidic\u201d proton between the two basic carbon atoms after protonation.\n                  <\/jats:p>","DOI":"10.1002\/anie.201612446","type":"journal-article","created":{"date-parts":[[2017,2,23]],"date-time":"2017-02-23T04:41:40Z","timestamp":1487824900000},"page":"3090-3093","source":"Crossref","is-referenced-by-count":28,"title":["A Phosphorus Bisylide: Exploring a New Class of Superbases with Two Interacting Carbon Atoms as Basicity Centers"],"prefix":"10.1002","volume":"56","author":[{"given":"Julius F.","family":"K\u00f6gel","sequence":"first","affiliation":[{"name":"Fachbereich Chemie Philipps-Universit\u00e4t Marburg  Hans-Meerwein-Strasse 35032 Marburg Germany"},{"name":"FB Biologie\/Chemie Universit\u00e4t Bremen  Leobener Str. im NW2 28359 Bremen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Davor","family":"Margeti\u0107","sequence":"additional","affiliation":[{"name":"Ru\u0111er Bo\u0161kovi\u0107 Institute  Bijeni\u010dka c. 54 10001 Zagreb Croatia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiulan","family":"Xie","sequence":"additional","affiliation":[{"name":"Fachbereich Chemie Philipps-Universit\u00e4t Marburg  Hans-Meerwein-Strasse 35032 Marburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lars H.","family":"Finger","sequence":"additional","affiliation":[{"name":"Fachbereich Chemie Philipps-Universit\u00e4t Marburg  Hans-Meerwein-Strasse 35032 Marburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"J\u00f6rg","family":"Sundermeyer","sequence":"additional","affiliation":[{"name":"Fachbereich Chemie Philipps-Universit\u00e4t Marburg  Hans-Meerwein-Strasse 35032 Marburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2017,2,23]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/9780470740859"},{"key":"e_1_2_2_2_1","doi-asserted-by":"crossref","first-page":"1055","DOI":"10.1002\/jlac.199619960705","author":"Schwesinger R.","year":"1996","journal-title":"Liebigs Ann. 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We assume linearity between the basicity scales in THF and MeCN. In contrast to the widely explored phosphazenes there is no literature data correlating the gas-phase basicity or proton affinity of P-ylides with their basicity in solution. Thus a reliable theoretical estimation of the pKBH+\u2005value of1on the MeCN scale was not possible."},{"key":"e_1_2_2_40_1","unstructured":"An extensive investigation of the basicity properties of bisylides will be the subject of a future publication."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201612446","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201612446","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,9]],"date-time":"2023-09-09T18:50:31Z","timestamp":1694285431000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201612446"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,2,23]]},"references-count":43,"journal-issue":{"issue":"11","published-print":{"date-parts":[[2017,3,6]]}},"alternative-id":["10.1002\/anie.201612446"],"URL":"https:\/\/doi.org\/10.1002\/anie.201612446","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,2,23]]}}}