Single crystal XRD, hirshfeld surface, vibrational and thermal studies on a new zwitterionic co-crystal of vitaminB3 (nicotinic acid)

Latha, M.M.; Novena, L. Mary; Athimoolam, S.; Sridhar, Balasubramanian

doi:10.1016/j.molstruc.2019.127578

Cited by 6 publications

(3 citation statements)

References 13 publications

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“…The calculations were performed using the GAUSSIAN09 program package (Frisch et al, 2009) installed at the SKIF 'Cyberia' supercomputer of the National Research Tomsk State University. Density functional theory (DFT) with hybrid functional B3LYP (Lee et al, 1988;Becke, 1993) and the 6-311++G(d,p) split-valence basis set, with the addition of polarization and diffuse functions for heavy and H atoms, was used since this method provides a good correlation of the calculation results with the experiment (Latha et al, 2020;Jyothi et al, 2019;Thangarasu et al, 2018;Prabha et al, 2017).…”

Section: Model Calculationsmentioning

confidence: 99%

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

Arkhipov

Фатеев

et al. 2020

Acta Crystallogr Sect B

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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.

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Section: Model Calculationsmentioning

confidence: 99%

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

Arkhipov

Фатеев

et al. 2020

Acta Crystallogr Sect B

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“…Various cocrystals of NA such as 3,5-dinitrobenzoic acidnicotinic acid (Ford et al, 2013), 4-aminobenzoic acid-nicotinic acid (Jebas & Balasubramanian, 2006), dipicolinic acidnicotinic acid (Bankiewicz & Wojtulewski, 2019), gallic acidnicotinic acid (Kavuru et al, 2010), modafinil-nicotinic acid (Ghosh et al, 2021) and p-hydroxybenzoic acid-nicotinic acid (Latha et al, 2020) have been reported. It is, therefore, of great interest to develop new formulations or functional solid state forms of NA through cocrystallization.…”

Section: Introductionmentioning

confidence: 99%

Crystal engineering of co-crystal of nicotinic acid and pyrogallol: an experimental and theoretical electron density analysis

Iqbal¹,

Mehmood²,

Noureen³

et al. 2021

Acta Crystallogr Sect B

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Experimental electron density analysis by means of high-resolution X-ray diffraction data up to sinθ/λmax = 1.11 Å−1 at 100 (1) K has been performed to analyze the detailed structure and the strength of intermolecular interactions responsible for the formation of a new solid form of nicotinic acid (NA), cocrystallized with pyrogallol (PY). There are two NA–PY units in the asymmetric unit. The experimental results are compared with the results obtained from theoretical structure factors modeled using periodic boundary DFT calculations. Both refinements were carried out using the Hansen and Coppens multipolar formalism (in MoPro program). The non-centrosymmetric and polar nature of the crystal system rendered the multipolar refinement challenging which was addressed by involving the transferability principle. This study highlights the significance of the transferability principle in electron density modeling in non-routine situations. The 2:2 cocrystal of NA–PY exhibits a zigzag, brickwall and sheet-like layered structure in three dimensions and is stabilized by strong intra- and inter-molecular hydrogen bonding through N—H...O and O—H...O bonds, some of them due to the zwitterion nature of NA as well as weak interactions between the PY molecules. Ranking these interactions via topological analysis of the electron density shows the leading role of the NA–NA substructure which drives the organization of the cocrystals. These strong interactions between the NA zwitterions may explain why Z′ = 2.

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“…18 Nicotinic acid contains a pyridine ring and carboxyl group that are preferentially involved in supramolecular synthon formation. In view of its wider significance, it has been used as an API (active pharmaceutical ingredient) to be cocrystallized with a variety of coformers, such as 4-aminobenzoic acid-nicotinic acid (2/1) co-crystal, 19 hesperetin-nicotinic acid co-crystal, 20 gallic acid-nicotinic acid, 20 3,5-dinoitrobenzoic acid-nicotinic acid molecular complex, 21 nicotinium p-hydroxybenzoic acid monohydrate, 22 dipicolinic acid-nicotinic acid zwitterionic co-crystal, 23 modafinil-nicotinic acid co-crystal, 24 and pyrogallol-nicotinic acid co-crystal. 25,26 Gallic acid (3,4,5-trihydroxybenzoic acid) monohydrate, a naturally occurring dietary triphenol, 27 is an ideal co-former in co-crystallization.…”

Section: Introductionmentioning

confidence: 99%

Crystal engineering, electron density analysis, andin situvariable temperature studies on co-crystal between nicotinic acid and gallic acid sesquihydrate

et al. 2023

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Single crystal XRD, hirshfeld surface, vibrational and thermal studies on a new zwitterionic co-crystal of vitaminB3 (nicotinic acid)

Cited by 6 publications

References 13 publications

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

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

Crystal engineering of co-crystal of nicotinic acid and pyrogallol: an experimental and theoretical electron density analysis

Crystal engineering, electron density analysis, andin situvariable temperature studies on co-crystal between nicotinic acid and gallic acid sesquihydrate

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