Focus on Physico‐Chemical Properties of Sulfoximines: Acidity, Basicity and Lipophilicity
Despite the numerous published syntheses and applications of sulfoximines, very few studies describe their physico-chemical properties and in particular their acidic, basic and lipophilic or hydrophilic characters. We report for the first time the acidity values (pK<sub>a</sub>) of fluorinated sulfoximines in water and in acetonitrile, as well as the basicity (pK<sub>aH</sub>) measurements of fluorinated and non-fluorinated sulfoximines in acetonitrile. The same sulfoximine library was also studied in terms of lipophilicity with measurement of the Hansch parameters of the sulfoximine moieties. Finally, these new data allowed us to optimize the N-alkylation reaction of fluorinated sulfoximines.
Authors
- Thierry Billard (ORCID: https://orcid.org/0000-0002-2937-9523)
- Märt Lõkov (ORCID: https://orcid.org/0000-0003-4484-0864)
- Bénédicte Claude-Montigny (ORCID: https://orcid.org/0000-0003-1212-9322)
- Sofja Tshepelevitsh (ORCID: https://orcid.org/0000-0002-7734-9310)
- Elsa Anselmi (ORCID: https://orcid.org/0000-0003-2996-2775)
- Ivo Leito (ORCID: https://orcid.org/0000-0002-3000-4964)
- Emmanuel Magnier (ORCID: https://orcid.org/0000-0003-3392-3971)
- Carmen Kesküla
- Jan Erik Soosaar
Institutions
- Université Claude Bernard Lyon 1 (FR)
- Université de Tours (FR)
- Centre National de la Recherche Scientifique (FR)
- Université de Versailles Saint-Quentin-en-Yvelines (FR)
- Université Paris-Saclay (FR)
- Tartu University Hospital (EE)
- Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (FR)
- Institut Lavoisier de Versailles (FR)
- University of Tartu (EE)
- École d'Ingénieurs en Chimie et Sciences du Numérique (FR)
Publication Details
- Journal
- Chemistry - A European Journal
- Published
- 2024-10-28
- DOI
- https://doi.org/10.1002/chem.202402329
- Citations
- 8
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 2.00
Funders
- Eesti Teadusagentuur
- Centre National de la Recherche Scientifique
- Tartu Ülikool