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Some six\u2010membered rings containing an endocyclic phosphorus atom and a \u03b2\u2010fluorine substituent that can interconvert to axial (<jats:italic>gauche<\/jats:italic> relative to phosphorus) and equatorial positions were then analysed. While phosphines do not establish an electrostatic attraction between fluorine and phosphorus, some oxidised forms exhibit surprising stability for the sterically disfavoured axial orientation. Because the nature of this behaviour was not obvious, since an intramolecular hydrogen bond can appear, a phosphonium derivative was further studied and its axial conformation was found to be highly stable. A preference for the <jats:italic>gauche<\/jats:italic> arrangement appears even for the acyclic and sterically hindered (2\u2010fluoroethyl)triphenylphosphonium cation. On the other hand, (ethane\u20101,2\u2010diyl)bis(phosphonium) cations are exclusively in <jats:italic>anti<\/jats:italic> conformation due to an (+\/+)\u2010electrostatic repulsion between the positively charged phosphonium groups.<\/jats:p>","DOI":"10.1002\/cphc.202100856","type":"journal-article","created":{"date-parts":[[2022,1,7]],"date-time":"2022-01-07T10:13:43Z","timestamp":1641550423000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Theoretical and X\u2010Ray Evidence of Electrostatic Phosphonium <i>anti<\/i> and <i>gauche<\/i> Effects"],"prefix":"10.1002","volume":"23","author":[{"given":"Francisco A.","family":"Martins","sequence":"first","affiliation":[{"name":"Department of Chemistry Institute of Natural Sciences Federal University of Lavras  MG, 37200-900 Lavras Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Poliane","family":"Chagas","sequence":"additional","affiliation":[{"name":"Department of Chemistry Institute of Exact Sciences Federal University of Minas Gerais  MG, 31270-901 Belo Horizonte Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"S\u00e9rgio S.","family":"Thomasi","sequence":"additional","affiliation":[{"name":"Department of Chemistry Institute of Natural Sciences Federal University of Lavras  MG, 37200-900 Lavras Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Luiz C. 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