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A number of different core structures of non\u2010ionic organosuperbases are considered (such as phosphazenes, guanidinophosphazenes, guanidino phosphorus ylides). A simple model for describing the dependence of basicity on the extent of the molecular framework is proposed, validated, and used for quantitatively predicting the ultimate basicities of different compound families and the rates of substituent effect saturation. Some of the considered bases (guanidino phosphorus carbenes) are expected to reach gas\u2010phase basicity around 370\u2005kcal\u2009mol<jats:sup>\u22121<\/jats:sup>, thus being the most basic neutral bases ever reported. Also, the classical substituted alkylphosphazenes were predicted to reach p<jats:italic>K<\/jats:italic><jats:sub>a<\/jats:sub> values of around 50 in acetonitrile, which is significantly higher than previously expected.<\/jats:p>","DOI":"10.1002\/anie.201503345","type":"journal-article","created":{"date-parts":[[2015,6,18]],"date-time":"2015-06-18T20:33:01Z","timestamp":1434659581000},"page":"9262-9265","source":"Crossref","is-referenced-by-count":81,"title":["Basicity Limits of Neutral Organic Superbases"],"prefix":"10.1002","volume":"54","author":[{"given":"Ivo","family":"Leito","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ilmar A.","family":"Koppel","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ivar","family":"Koppel","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Karl","family":"Kaupmees","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sofja","family":"Tshepelevitsh","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jaan","family":"Saame","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2015,6,18]]},"reference":[{"key":"e_1_2_2_1_2","volume-title":"Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts","year":"2009"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.progpolymsci.2011.05.005"},{"key":"e_1_2_2_3_2","doi-asserted-by":"crossref","first-page":"1055","DOI":"10.1002\/jlac.199619960705","author":"Schwesinger R.","year":"1996","journal-title":"Liebigs Ann."},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100458v"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp012168s"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0547533"},{"key":"e_1_2_2_7_2","unstructured":"\u00a0"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja052647v"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja409760z"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201000828"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201102249"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja053543n"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201307212"},{"key":"e_1_2_2_13_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201307212"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja906618g"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39950001267"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja3015764"},{"key":"e_1_2_2_17_2","unstructured":"\u00a0"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp401076j"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1039\/c4cp01394h"},{"key":"e_1_2_2_20_2","volume-title":"Ylides and Imines of Phosphorus","author":"Johnson A. 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See the Supporting Information for details."},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.556018"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo034537h"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0166-1280(03)00540-2"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201503345","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201503345","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,16]],"date-time":"2023-10-16T05:30:44Z","timestamp":1697434244000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201503345"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,6,18]]},"references-count":28,"journal-issue":{"issue":"32","published-print":{"date-parts":[[2015,8,3]]}},"alternative-id":["10.1002\/anie.201503345"],"URL":"https:\/\/doi.org\/10.1002\/anie.201503345","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2015,6,18]]}}}