Crystal Structures of d-Lyxono-1,4-lactone and Its O-Tosyl Derivative - Publication - Bridge of Knowledge

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Crystal Structures of d-Lyxono-1,4-lactone and Its O-Tosyl Derivative

Abstract

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- O-isopropylidene-D-lyxono-1,4-lactone was formed, which in a further step led to the formation of a 2-O-tosyl derivative. Its structure was confirmed by X-ray diffraction analysis. The additional ring of the O-isopropylidene derivative caused the lactone ring to change conformation to 3E. In the crystal structure of this compound, only C-H···O intermolecular interactions were present, as confirmed by the Hirshfeld surface analysis.

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Category:
Articles
Type:
artykuły w czasopismach
Published in:
MOLECULES no. 30,
ISSN: 1420-3049
Language:
English
Publication year:
2025
Bibliographic description:
Sosnowska A., Chojnacki J., Samaszko-Fiertek J., Madaj J., Dmochowska B.: Crystal Structures of d-Lyxono-1,4-lactone and Its O-Tosyl Derivative// MOLECULES -Vol. 30,iss. 2 (2025), s.287-
DOI:
Digital Object Identifier (open in new tab) 10.3390/molecules30020287
Sources of funding:
  • Free publication
Verified by:
Gdańsk University of Technology

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