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 | Sciact - CRIS-system of Boreskov Institute of Catalysis

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 Full article

Journal

Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
ISSN: 2052-5192 , E-ISSN: 2052-5206

Output data

Year: 2020, Volume: B76, Number: 6, Pages: 967-978 Pages count : 12 DOI: 10.1107/s2052520620012421

Tags

Cocrystal; L-ascorbic acid; vitamin C; picolinic acid; energy of hydrogen bond; IR and Raman spectroscopy; DFT; Mulliken populations; Voronoi charge; Hirshfeld charge; conformations of molecules; root-mean-square deviation of atomic positions (RMSD)

Authors

Evtushenko Diana N. ¹ , Arkhipov Sergey G. ^2,3 , Fateev Alexander V. ^4,1 , Izaak Tatyana I. ¹ , Egorova Lidia A. ¹ , Skorik Nina A. ¹ , Vodyankina Olga V. ¹ , Boldyreva Elena V. ^2,3

Affiliations

1	National Research Tomsk State University, Lenin Ave. 36, Tomsk, 634050, Russian Federation
2	Boreskov Institute of Catalysis SB RAS, Lavrentiev Ave. 5, Novosibirsk, 630090, Russian Federation
3	Novosibirsk State University, Pirogova str. 2, Novosibirsk, 630090, Russian Federation
4	Tomsk State Pedagogical University, Kievskaya str. 60, Tomsk, 634061, Russian Federation

Funding (2)

1	The Ministry of Education and Science of the Russian Federation	8.2.03.2018
2	Ministry of Science and Higher Education of the Russian Federation	0239-2019-0003

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.

Evtushenko D.N. , Arkhipov S.G. , Fateev A.V. , Izaak T.I. , Egorova L.A. , Skorik N.A. , Vodyankina O.V. , Boldyreva E.V.
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
Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials. 2020. V.B76. N6. P.967-978. DOI: 10.1107/s2052520620012421 WOS Scopus РИНЦ AN PMID OpenAlex

Submitted:	Mar 24, 2020
Accepted:	Sep 9, 2020
Published online:	Nov 3, 2020
Published print:	Dec 1, 2020

Web of science:	WOS:000598176500002
Scopus:	2-s2.0-85097578100
Elibrary:	45082473
Chemical Abstracts:	2020:2494715
PMID:	33289709
OpenAlex:	W3095359694

DB	Citing
Scopus	7
Web of science	7
Elibrary	9
OpenAlex	6