A cocrystal of L-ascorbic acid with picolinic acid: the role of O-H...O, N-H...O and C-H...O hydrogen bonds and L-ascorbic acid conformation in structure stabilization

Diana N. Evtushenko, Sergey G. Arkhipov, Alexander V. Fateev, Tatyana I. Izaak, Lidia A. Egorova, Nina A. Skorik, Olga V. Vodyankina, Elena V. Boldyreva

Research output: Contribution to journalArticlepeer-review

Abstract

A new 1:1 cocrystal (L-Asc-Pic) of L-ascorbic acid (vitamin C) with picolinic acid was prepared as a powder and as single crystals. The crystal structure was solved and refined from single-crystal X-ray diffraction (SCXRD) data collected at 293 (2) and 100 (2) K. The samples of the L-Asc-Pic cocrystal were characterized by elemental (HCNS) analysis and titrimetric methods, TG/DTG/DSC, and IR and Raman spectroscopy. The asymmetric unit comprises a picolinic acid zwitterion and an L-ascorbic acid molecule. The stabilization energy of intermolecular interactions involving hydrogen bonds, the vibrational spectrum and the energies of the frontier molecular orbitals were calculated using the GAUSSIAN09 and the CrystalExplorer17 programs. The charge distribution on the atoms of the L-Asc-Pic cocrystal, L-ascorbic acid itself and its 12 known cocrystals (structures from Version 5.40 of the Cambridge Structural Database) were calculated by the methods of Mulliken, Voronoi and Hirshfeld charge analyses (ADF) at the bp86/TZ2P+ level of theory. The total effective charges and conformations of the L-ascorbic acid molecules in the new and previously reported cocrystals were compared with those of the two symmetry-independent molecules in the crystals of L-ascorbic acid. A correlation between molecular conformation and its effective charge is discussed.

Original languageEnglish
Pages (from-to)967-978
Number of pages12
JournalActa crystallographica Section B, Structural science, crystal engineering and materials
Volume76
Issue numberPt 6
DOIs
Publication statusPublished - 1 Dec 2020
Externally publishedYes

Keywords

  • cocrystal
  • conformations of molecules
  • DFT
  • energy of hydrogen bond
  • Hirshfeld charge
  • IR and Raman spectroscopy
  • l-ascorbic acid
  • Mulliken populations
  • picolinic acid
  • root-mean-square deviation of atomic positions (RMSD)
  • vitamin C
  • Voronoi charge
  • L-ascorbic acid
  • GRAPH-SET ANALYSIS
  • PATTERNS
  • CRYSTAL
  • AMINO-ACIDS
  • X-RAY

OECD FOS+WOS

  • 1.04 CHEMICAL SCIENCES
  • 1.04.FI CRYSTALLOGRAPHY

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