Cocrystals of Gallic Acid with Urea and Propionamide: Supramolecular Structures, Hirshfeld Surface Analysis, and DFT Studies

Jyothi, K.; Gautam, Rekha; Swain, Diptikanta; Row, Tayur N. Guru; Lokanath, N.K.

doi:10.1002/crat.201900016

Cited by 14 publications

(7 citation statements)

References 33 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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“…Gallic acid (3,4,5-trihydroxybenzoic acid) is a common active pharmaceutical ingredient (API) (Jyothi et al, 2019). It exhibits antioxidant, antimicrobial and anticancer properties, and it is used in therapeutic applications for inflammatory allergic diseases (Choubey et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

“…The pK a value of gallic acid is 4.4. Based on pK a differences with acidic or basic coformers, gallic acid has the ability to form both salts and cocrystals (Jyothi et al, 2019;Childs et al, 2007). In the various polymorphs of gallic acid, the most common packing motif is the acidÀacid homosynthon.…”

Section: Introductionmentioning

confidence: 99%

π-Hole bonding in a new co-crystal hydrate of gallic acid and pyrazine: static and dynamic charge density analysis

Pal¹,

Jelsch²,

Momma³

et al. 2022

Acta Crystallogr Sect B

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A new cocrystal hydrate of gallic acid with pyrazine (4GA, Py, 4H2O; GA4PyW4) was obtained and characterized by single crystal X-ray diffraction. In addition to structure determination, experimental charge density analysis was carried out in terms of Multipole Modelling (MP), X-ray wavefunction refinement (XWR) and maximum entropy method (MEM). As a part of XWR, the structural refinement via Hirshfeld atom refinement was carried out and resulted in O—H bond lengths close to values from neutron diffraction. A systematic comparison of molecular conformations and aromatic interactions in this new cocrystal hydrate was performed with other existing polymorphs of gallic acid. In GA4PyW4, the two symmetry-independent gallic acid molecules have a syn COOH orientation and form the common (COOH)2 dimeric synthon. The carboxyl C atom displays the characteristics of π-holes with electropositive regions above and below the molecular plane and engages in acceptor–donor interactions with oxygen atoms of acidic O—H groups and phenol groups of neighbouring gallic acid molecules. The signature of the π-hole was identified from experimental charge density analysis, both in static density maps in MP and XWR as well as dynamic density in MEM, but it cannot be pinned down to a specific atom–atom interaction. This study presents the first comparison between an XWR and a MEM experimental electron-density determination.

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“…Further, the adjacent red and blue triangles on the shape index surface and flat regions on the curvedness surface reveal the presence of π–π stacking in the molecule (Figure 6F). [ 60,61 ]…”

Section: Resultsmentioning

confidence: 99%

Synthesis, structure, Hirshfeld surface, DFT, and molecular docking studies of a new organic cocrystal: creatinine:2,3‐pyridinedicarboxylic acid

Matheswari

Asha

Bhuvanesh

et al. 2021

J of Physical Organic Chem

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A new cocrystal (CR:2,3PDCA) of creatinine (CR) with 2,3‐pyridine dicarboxylic acid (2,3PDCA) was grown by slow evaporation method, and its crystal structure was characterized by single‐crystal X‐ray diffraction (SCXRD) analysis. The cocrystal was found to be triclinic with space group P‐1 and lattice parameters a = 7.3610(7) Å, b = 8.7813(9) Å, and C = 9.4173(10) Å. The intermolecular hydrogen bonds, namely, N‐H…N and C‐O…H‐N interactions, together play a major role in stabilizing the cocrystal. Further, the molecular interactions in the crystal structure were analyzed by considering short contacts and intermolecular contactsusing Hirshfeld surface methods. Furthermore, the coordinates of cocrystal were obtained by DFT calculations using the B3LYP method with a 6‐311++G (d,p) basis set. Besides this, other molecular properties such as frontier molecular orbital, HOMO‐LUMO energies, and Mulliken charge analysis were also reported. Furthermore, a molecular docking study was performed to study the anti‐inflammatory property of the cocrystal using the Auto‐Dock vina program by investigating the binding patterns of the synthesized cocrystal into a 1R35 inhibitor. In vitro anti‐microbial activities against some bacterial and fungal strains were also investigated.

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Cocrystals of Gallic Acid with Urea and Propionamide: Supramolecular Structures, Hirshfeld Surface Analysis, and DFT Studies

Cited by 14 publications

References 33 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

π-Hole bonding in a new co-crystal hydrate of gallic acid and pyrazine: static and dynamic charge density analysis

Synthesis, structure, Hirshfeld surface, DFT, and molecular docking studies of a new organic cocrystal: creatinine:2,3‐pyridinedicarboxylic acid

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