Crystal Structures of <span style="font-variant: small-caps">d</span>-Lyxono-1,4-lactone and Its <i>O</i>-Tosyl Derivative
γ- and δ-lactones were formed by bromine oxidation of commercially available D-lyxose, as confirmed by IR analysis. The former was isolated, and its structure was confirmed by NMR spectra and X-ray analysis. In this structure, the presence of both intermolecular and intramolecular hydrogen bonds was...
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2025-01-01
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| author | Anna Sosnowska Jarosław Chojnacki Justyna Samaszko-Fiertek Janusz Madaj Barbara Dmochowska |
| author_facet | Anna Sosnowska Jarosław Chojnacki Justyna Samaszko-Fiertek Janusz Madaj Barbara Dmochowska |
| author_sort | Anna Sosnowska |
| collection | DOAJ |
| description | γ- and δ-lactones were formed by bromine oxidation of commercially available D-lyxose, as confirmed by IR analysis. The former was isolated, and its structure was confirmed by NMR spectra and X-ray analysis. In this structure, the presence of both intermolecular and intramolecular hydrogen bonds was found. Intermolecular interactions in the crystal were illustrated using the Hirshfeld surfaces. Due to steric reasons, 3,5-<i>O</i>-isopropylidene-<span style="font-variant: small-caps;">d</span>-lyxono-1,4-lactone was formed, which in a further step led to the formation of a 2-<i>O</i>-tosyl derivative. Its structure was confirmed by X-ray diffraction analysis. The additional ring of the <i>O</i>-isopropylidene derivative caused the lactone ring to change conformation to <i><sup>3</sup>E</i>. In the crystal structure of this compound, only C-H⸱⸱⸱O intermolecular interactions were present, as confirmed by the Hirshfeld surface analysis. |
| format | Article |
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| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj-art-40b4f8ac10824eb5a2a4c0cad11a4a5c2025-01-24T13:43:25ZengMDPI AGMolecules1420-30492025-01-0130228710.3390/molecules30020287Crystal Structures of <span style="font-variant: small-caps">d</span>-Lyxono-1,4-lactone and Its <i>O</i>-Tosyl DerivativeAnna Sosnowska0Jarosław Chojnacki1Justyna Samaszko-Fiertek2Janusz Madaj3Barbara Dmochowska4Faculty of Chemistry, University of Gdansk, Wita Stwosza 63, 80-308 Gdansk, PolandDepartment of Inorganic Chemistry, GdańskTech, G. Narutowicza 11/12, 80-233 Gdansk, PolandFaculty of Chemistry, University of Gdansk, Wita Stwosza 63, 80-308 Gdansk, PolandFaculty of Chemistry, University of Gdansk, Wita Stwosza 63, 80-308 Gdansk, PolandFaculty of Chemistry, University of Gdansk, Wita Stwosza 63, 80-308 Gdansk, Polandγ- and δ-lactones were formed by bromine oxidation of commercially available D-lyxose, as confirmed by IR analysis. The former was isolated, and its structure was confirmed by NMR spectra and X-ray analysis. In this structure, the presence of both intermolecular and intramolecular hydrogen bonds was found. Intermolecular interactions in the crystal were illustrated using the Hirshfeld surfaces. Due to steric reasons, 3,5-<i>O</i>-isopropylidene-<span style="font-variant: small-caps;">d</span>-lyxono-1,4-lactone was formed, which in a further step led to the formation of a 2-<i>O</i>-tosyl derivative. Its structure was confirmed by X-ray diffraction analysis. The additional ring of the <i>O</i>-isopropylidene derivative caused the lactone ring to change conformation to <i><sup>3</sup>E</i>. In the crystal structure of this compound, only C-H⸱⸱⸱O intermolecular interactions were present, as confirmed by the Hirshfeld surface analysis.https://www.mdpi.com/1420-3049/30/2/287D-lyxono-1,4-lactone<i>O</i>-tosyl derivativeX-ray crystallographyHirshfeld surfaceNMR |
| spellingShingle | Anna Sosnowska Jarosław Chojnacki Justyna Samaszko-Fiertek Janusz Madaj Barbara Dmochowska Crystal Structures of <span style="font-variant: small-caps">d</span>-Lyxono-1,4-lactone and Its <i>O</i>-Tosyl Derivative Molecules D-lyxono-1,4-lactone <i>O</i>-tosyl derivative X-ray crystallography Hirshfeld surface NMR |
| title | Crystal Structures of <span style="font-variant: small-caps">d</span>-Lyxono-1,4-lactone and Its <i>O</i>-Tosyl Derivative |
| title_full | Crystal Structures of <span style="font-variant: small-caps">d</span>-Lyxono-1,4-lactone and Its <i>O</i>-Tosyl Derivative |
| title_fullStr | Crystal Structures of <span style="font-variant: small-caps">d</span>-Lyxono-1,4-lactone and Its <i>O</i>-Tosyl Derivative |
| title_full_unstemmed | Crystal Structures of <span style="font-variant: small-caps">d</span>-Lyxono-1,4-lactone and Its <i>O</i>-Tosyl Derivative |
| title_short | Crystal Structures of <span style="font-variant: small-caps">d</span>-Lyxono-1,4-lactone and Its <i>O</i>-Tosyl Derivative |
| title_sort | crystal structures of span style font variant small caps d span lyxono 1 4 lactone and its i o i tosyl derivative |
| topic | D-lyxono-1,4-lactone <i>O</i>-tosyl derivative X-ray crystallography Hirshfeld surface NMR |
| url | https://www.mdpi.com/1420-3049/30/2/287 |
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