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. / Evtushenko, Diana N.; Arkhipov, Sergey G.; Fateev, Alexander V. et al.
In: Acta crystallographica Section B, Structural science, crystal engineering and materials, Vol. 76, No. Pt 6, 01.12.2020, p. 967-978.Research output: Contribution to journal › Article › peer-review
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TY - JOUR
T1 - A cocrystal of L-ascorbic acid with picolinic acid
T2 - the role of O-H...O, N-H...O and C-H...O hydrogen bonds and L-ascorbic acid conformation in structure stabilization
AU - Evtushenko, Diana N.
AU - Arkhipov, Sergey G.
AU - Fateev, Alexander V.
AU - Izaak, Tatyana I.
AU - Egorova, Lidia A.
AU - Skorik, Nina A.
AU - Vodyankina, Olga V.
AU - Boldyreva, Elena V.
N1 - Publisher Copyright: © 2020 International Union of Crystallography. All rights reserved.
PY - 2020/12/1
Y1 - 2020/12/1
N2 - 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.
AB - 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.
KW - cocrystal
KW - conformations of molecules
KW - DFT
KW - energy of hydrogen bond
KW - Hirshfeld charge
KW - IR and Raman spectroscopy
KW - l-ascorbic acid
KW - Mulliken populations
KW - picolinic acid
KW - root-mean-square deviation of atomic positions (RMSD)
KW - vitamin C
KW - Voronoi charge
KW - L-ascorbic acid
KW - GRAPH-SET ANALYSIS
KW - PATTERNS
KW - CRYSTAL
KW - AMINO-ACIDS
KW - X-RAY
UR - http://www.scopus.com/inward/record.url?scp=85097578100&partnerID=8YFLogxK
U2 - 10.1107/S2052520620012421
DO - 10.1107/S2052520620012421
M3 - Article
C2 - 33289709
AN - SCOPUS:85097578100
VL - 76
SP - 967
EP - 978
JO - Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
JF - Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
SN - 2052-5192
IS - Pt 6
ER -
ID: 26715276