Crystal structures of three salts of the triphenylsulfonium ion
The reactions of triphenylsulfonium chloride ([TPS][Cl]) with various acids in methanol yield the corresponding salts triphenylsulfonium triiodide, C18H15S+·I3− or [TPS][I3] (I), triphenylsulfonium perchlorate, C18H15S+·ClO4− or [TPS][ClO4] (II), and triphenylsulfonium hexafluorophosphate, C18H15S+·...
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International Union of Crystallography
2025-02-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
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| Online Access: | https://journals.iucr.org/paper?S2056989025000118 |
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| author | Rylan Artis Waylan Callaway Elizabeth Heyward Naomi Reyes Gavin Roberts Kaitlyn Van Ostenbridge Clifford W. Padgett Will E. Lynch |
| author_facet | Rylan Artis Waylan Callaway Elizabeth Heyward Naomi Reyes Gavin Roberts Kaitlyn Van Ostenbridge Clifford W. Padgett Will E. Lynch |
| author_sort | Rylan Artis |
| collection | DOAJ |
| description | The reactions of triphenylsulfonium chloride ([TPS][Cl]) with various acids in methanol yield the corresponding salts triphenylsulfonium triiodide, C18H15S+·I3− or [TPS][I3] (I), triphenylsulfonium perchlorate, C18H15S+·ClO4− or [TPS][ClO4] (II), and triphenylsulfonium hexafluorophosphate, C18H15S+·PF6− or [TPS][PF6] (III), as crystalline products. These crystals were structurally characterized by single-crystal X-ray diffraction. In all three compounds, the sulfur atom in the triphenylsulfonium cation adopts a distorted trigonal–pyramidal geometry. [TPS][I3] (I) and [TPS][PF6] (III) both crystallize in the space group P21/n, while [TPS][ClO4] (II) crystallizes in P21. The S—C bond lengths are comparable across the three salts, and the S—C—S bond angles are consistently between 102 and 106°. Hirshfeld surface analyses reveal that each structure is dominated by hydrogen-based intermolecular contacts, supplemented by anion-specific interactions such as I...H in (I), O...H in (II), and F...H in (III). These contacts organize the ions into mono-periodic ribbon- or chain-like arrangements. No significant π–π stacking is observed. |
| format | Article |
| id | doaj-art-f3bfbfd373784e04838e41b65cae74cc |
| institution | Kabale University |
| issn | 2056-9890 |
| language | English |
| publishDate | 2025-02-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj-art-f3bfbfd373784e04838e41b65cae74cc2025-02-06T07:27:16ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902025-02-0181211411910.1107/S2056989025000118ej2011Crystal structures of three salts of the triphenylsulfonium ionRylan Artis0Waylan Callaway1Elizabeth Heyward2Naomi Reyes3Gavin Roberts4Kaitlyn Van Ostenbridge5Clifford W. Padgett6Will E. Lynch7Department of Biochemistry, Chemistry and Physics, Georgia Southern University, 11935 Abercorn Street Savannah GA 31419, USADepartment of Biochemistry, Chemistry and Physics, Georgia Southern University, 11935 Abercorn Street Savannah GA 31419, USADepartment of Biochemistry, Chemistry and Physics, Georgia Southern University, 11935 Abercorn Street Savannah GA 31419, USADepartment of Biochemistry, Chemistry and Physics, Georgia Southern University, 11935 Abercorn Street Savannah GA 31419, USADepartment of Biochemistry, Chemistry and Physics, Georgia Southern University, 11935 Abercorn Street Savannah GA 31419, USADepartment of Biochemistry, Chemistry and Physics, Georgia Southern University, 11935 Abercorn Street Savannah GA 31419, USADepartment of Biochemistry, Chemistry and Physics, Georgia Southern University, 11935 Abercorn Street Savannah GA 31419, USADepartment of Biochemistry, Chemistry and Physics, Georgia Southern University, 11935 Abercorn Street Savannah GA 31419, USAThe reactions of triphenylsulfonium chloride ([TPS][Cl]) with various acids in methanol yield the corresponding salts triphenylsulfonium triiodide, C18H15S+·I3− or [TPS][I3] (I), triphenylsulfonium perchlorate, C18H15S+·ClO4− or [TPS][ClO4] (II), and triphenylsulfonium hexafluorophosphate, C18H15S+·PF6− or [TPS][PF6] (III), as crystalline products. These crystals were structurally characterized by single-crystal X-ray diffraction. In all three compounds, the sulfur atom in the triphenylsulfonium cation adopts a distorted trigonal–pyramidal geometry. [TPS][I3] (I) and [TPS][PF6] (III) both crystallize in the space group P21/n, while [TPS][ClO4] (II) crystallizes in P21. The S—C bond lengths are comparable across the three salts, and the S—C—S bond angles are consistently between 102 and 106°. Hirshfeld surface analyses reveal that each structure is dominated by hydrogen-based intermolecular contacts, supplemented by anion-specific interactions such as I...H in (I), O...H in (II), and F...H in (III). These contacts organize the ions into mono-periodic ribbon- or chain-like arrangements. No significant π–π stacking is observed.https://journals.iucr.org/paper?S2056989025000118crystal structuretriphenylsulfonium ionsalts |
| spellingShingle | Rylan Artis Waylan Callaway Elizabeth Heyward Naomi Reyes Gavin Roberts Kaitlyn Van Ostenbridge Clifford W. Padgett Will E. Lynch Crystal structures of three salts of the triphenylsulfonium ion Acta Crystallographica Section E: Crystallographic Communications crystal structure triphenylsulfonium ion salts |
| title | Crystal structures of three salts of the triphenylsulfonium ion |
| title_full | Crystal structures of three salts of the triphenylsulfonium ion |
| title_fullStr | Crystal structures of three salts of the triphenylsulfonium ion |
| title_full_unstemmed | Crystal structures of three salts of the triphenylsulfonium ion |
| title_short | Crystal structures of three salts of the triphenylsulfonium ion |
| title_sort | crystal structures of three salts of the triphenylsulfonium ion |
| topic | crystal structure triphenylsulfonium ion salts |
| url | https://journals.iucr.org/paper?S2056989025000118 |
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