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Quantum chemical calculations on perfluoroalkylated silanides show significantly lower HOMO and LUMO energy levels in comparison to their non\u2010fluorinated counterparts, which implies reduced Lewis basicity and increased Lewis acidity of the [Si(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>3<\/jats:sub>]<jats:sup>\u2212<\/jats:sup> ion. With these findings and a HOMO\u2013LUMO gap of 4.80\u2005eV similar to N\u2010heterocyclic silylenes (NHSis), perfluoroalkyl silanides are predestined to exhibit Lewis\u2010amphoteric character similar to silylenes. Deprotonation of Si(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>3<\/jats:sub>H with sterically demanding phosphazene bases afforded thermally stable phosphazenium salts of the [Si(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>3<\/jats:sub>]<jats:sup>\u2212<\/jats:sup> anion, which add to benzaldehyde, benzophenone, CS<jats:sub>2<\/jats:sub>, and CO<jats:sub>2<\/jats:sub> in various manners. This behavior also mirrors the reactivity of silylenes towards ketones as well as heterocumulenes and is rationalized by Lewis amphotericity being inherent in these silanides.<\/jats:p>","DOI":"10.1002\/anie.202016455","type":"journal-article","created":{"date-parts":[[2021,2,22]],"date-time":"2021-02-22T15:23:26Z","timestamp":1614007406000},"page":"12124-12131","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":24,"title":["Evidence of the Lewis\u2010Amphoteric Character of Tris(pentafluoroethyl)silanide, [Si(C<sub>2<\/sub>F<sub>5<\/sub>)<sub>3<\/sub>]<sup>\u2212<\/sup>"],"prefix":"10.1002","volume":"60","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7006-585X","authenticated-orcid":false,"given":"Natalia","family":"Tiessen","sequence":"first","affiliation":[{"name":"Universit\u00e4t Bielefeld Fakult\u00e4t f\u00fcr Chemie Centrum f\u00fcr Molekulare Materialien  Universit\u00e4tsstrasse 25 33615 Bielefeld Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2242-239X","authenticated-orcid":false,"given":"Mira","family":"Ke\u00dfler","sequence":"additional","affiliation":[{"name":"Universit\u00e4t Bielefeld Fakult\u00e4t f\u00fcr Chemie Centrum f\u00fcr Molekulare Materialien  Universit\u00e4tsstrasse 25 33615 Bielefeld Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Beate","family":"Neumann","sequence":"additional","affiliation":[{"name":"Universit\u00e4t Bielefeld Fakult\u00e4t f\u00fcr Chemie Centrum f\u00fcr Molekulare Materialien  Universit\u00e4tsstrasse 25 33615 Bielefeld Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hans\u2010Georg","family":"Stammler","sequence":"additional","affiliation":[{"name":"Universit\u00e4t Bielefeld Fakult\u00e4t f\u00fcr Chemie Centrum f\u00fcr Molekulare Materialien  Universit\u00e4tsstrasse 25 33615 Bielefeld Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9610-8478","authenticated-orcid":false,"given":"Berthold","family":"Hoge","sequence":"additional","affiliation":[{"name":"Universit\u00e4t Bielefeld Fakult\u00e4t f\u00fcr Chemie Centrum f\u00fcr Molekulare Materialien  Universit\u00e4tsstrasse 25 33615 Bielefeld Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,3,22]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","volume-title":"Frustrated Lewis Pairs I: Undercovering and Understanding","author":"Stephan D. 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