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Acetone forms the 1\u2009:\u20092 adduct SF<jats:sub>4<\/jats:sub>\u2009\u22c5\u2009[O=C(CH<jats:sub>3<\/jats:sub>)<jats:sub>2<\/jats:sub>]<jats:sub>2,<\/jats:sub> as well as the dimeric 1\u2009:\u20091 adducts [SF<jats:sub>4<\/jats:sub>\u2009\u22c5\u2009O=C(CH<jats:sub>3<\/jats:sub>)<jats:sub>2<\/jats:sub>]<jats:sub>2<\/jats:sub> as identified by low\u2010temperature Raman spectroscopy and, for the latter, X\u2010ray crystallography. In both adducts, SF<jats:sub>4<\/jats:sub> acts as a double chalcogen\u2010bond donor to two keto groups. In contrast 2\u2010adamantanone does not form an isolable solid adduct with SF<jats:sub>4<\/jats:sub>; in the presence of HF, however, it forms SF<jats:sub>4<\/jats:sub>\u2009\u22c5\u2009O=C<jats:sub>10<\/jats:sub>H<jats:sub>14<\/jats:sub>O\u2009\u22c5\u2009HF, which comprises chains with weak S\u2014O and S\u2014FH chalcogen bonds in the crystal structure. Sulfur tetrafluoride in this compound is readily lost at \u221285\u2009\u00b0C, leading to the isolation of C<jats:sub>10<\/jats:sub>H<jats:sub>14<\/jats:sub>O\u2009\u22c5\u2009HF at low temperature. Density functional theory (DFT) calculations aid in vibrational assignments and serve to describe the interactions of the keto group with SF<jats:sub>4<\/jats:sub> and HF, as well as interactions between SF<jats:sub>4<\/jats:sub> with HF. It is found that separate and combined CO\u2014HF and CO\u2014SF<jats:sub>4<\/jats:sub> chalcogen bonds do not polarize the C=O group to any significant degree.<\/jats:p>","DOI":"10.1002\/chem.202301068","type":"journal-article","created":{"date-parts":[[2023,4,21]],"date-time":"2023-04-21T10:46:02Z","timestamp":1682073962000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Interaction Modes Between SF<sub>4<\/sub> and Ketones; Study of Intermediates in Deoxofluorination Reactions"],"prefix":"10.1002","volume":"29","author":[{"given":"Daniel","family":"Stuart","sequence":"first","affiliation":[{"name":"Canadian Centre for Research in Advanced Fluorine Technologies and Department of Chemistry and Biochemistry University of Lethbridge  4401 University Drive Lethbridge AB T1\u2005K 3\u2005M4 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Felix","family":"O\u2018Donnell","sequence":"additional","affiliation":[{"name":"Canadian Centre for Research in Advanced Fluorine Technologies and Department of Chemistry and Biochemistry University of Lethbridge  4401 University Drive Lethbridge AB T1\u2005K 3\u2005M4 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5801-3942","authenticated-orcid":false,"given":"Stacey D.","family":"Wetmore","sequence":"additional","affiliation":[{"name":"Canadian Centre for Research in Advanced Fluorine Technologies and Department of Chemistry and Biochemistry University of Lethbridge  4401 University Drive Lethbridge AB T1\u2005K 3\u2005M4 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0821-089X","authenticated-orcid":false,"given":"Michael","family":"Gerken","sequence":"additional","affiliation":[{"name":"Canadian Centre for Research in Advanced Fluorine Technologies and Department of Chemistry and Biochemistry University of Lethbridge  4401 University Drive Lethbridge AB T1\u2005K 3\u2005M4 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,6]]},"reference":[{"key":"e_1_2_8_1_1","unstructured":"\u00a0"},{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp509212t"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CP04006D"},{"key":"e_1_2_8_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CP01033E"},{"key":"e_1_2_8_5_1","doi-asserted-by":"crossref","unstructured":"E.\u2005L. 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