The trimorphism of 3-hydroxybenzoic acid: an experimental and computational study

Braun, Doris E.

doi:10.1039/d1ce00159k

Cited by 4 publications

(7 citation statements)

References 47 publications

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“…Crystallization from solution of HKA and 3-HBA resulted in the formation of the cocrystal HKA·3-HBA. As listed in Table S2, pure 3-HBA is known to exist in three polymorphic modifications . Form I is the thermodynamically stable form, while form II and III are metastable.…”

Section: Results and Discussionmentioning

confidence: 99%

Section: Results and Discussionmentioning

confidence: 99%

“…As listed in Table S2, pure 3-HBA is known to exist in three polymorphic modifications. 55 Form I is the thermodynamically stable form, while form II and III are metastable. The commercial 3-HBA employed in the reaction with HKA was form I.…”

Section: Solid-state Structures Of Hka Cocrystals and Saltmentioning

confidence: 99%

“…Similarly to the cocrystallization experiments, cooling crystallization of 3-HBA (from ethyl acetate) resulted in form II, whereas grinding experiments favored the formation of form I. 55 We investigated the difference in cocrystal formation enthalpy, i.e. form I → cocrystal and form II → cocrystal.…”

Section: Solid-state Structures Of Hka Cocrystals and Saltmentioning

confidence: 99%

“…The reaction of HKA with the 3-hydroxybenzoic acid (3-HBA) resulted in a cocrystal with striking structural similarity with the crystal structures of both HKA and 3-HBA Form II, although the cocrystallization was conducted with 3-HBA Form I. Incidentally, the 3-HBA polymorphs have been recently investigated in detail by one of us. 55 For this reason, we decided to further explore the possible formation of cocrystals of HKA with molecules that are known to act as coformers in cocrystals of 3-hydroxybenzoic acid. To this end, a search in the CSD was conducted, and, among other systems, we selected molecular solids possessing interesting properties in the skin care or in the antibacterial fields, and therefore they could be used as enhancers of HKA properties.…”

Section: ■ Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Searching for Suitable Kojic Acid Coformers: From Cocrystals and Salt to Eutectics

Sun

Braun

Casali

et al. 2023

Crystal Growth & Design

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The possibility of obtaining cocrystals of kojic acid with organic coformers has been investigated by both computational and experimental approaches. Cocrystallization attempts have been carried out with about 50 coformers, in different stoichiometric ratios, by solution, slurry, and mechanochemical methods. Cocrystals were obtained with 3-hydroxybenzoic acid, imidazole, 4-pyridone, DABCO, and urotropine, while piperazine yielded a salt with the kojiate anion; cocrystallization with theophylline and 4-aminopyridine resulted in stoichiometric crystalline complexes that could not be described with certainty as cocrystals or salts. In the cases of panthenol, nicotinamide, urea, and salicylic acid the eutectic systems with kojic acid were investigated via differential scanning calorimetry. In all other preparations the resulting materials were constituted of a mixture of the reactants. All compounds were investigated by powder X-ray diffraction; the five cocrystals and the salt were fully characterized via single crystal X-ray diffraction. The stability of the cocrystals and the intermolecular interactions in all characterized compounds have been investigated by computational methods based on the electronic structure and pairwise energy calculations, respectively.

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Section: Results and Discussionmentioning

confidence: 99%

Section: Results and Discussionmentioning

confidence: 99%

Section: Solid-state Structures Of Hka Cocrystals and Saltmentioning

confidence: 99%

Section: Solid-state Structures Of Hka Cocrystals and Saltmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Searching for Suitable Kojic Acid Coformers: From Cocrystals and Salt to Eutectics

Sun

Braun

Casali

et al. 2023

Crystal Growth & Design

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Metronidazole Cocrystal Polymorphs with Gallic and Gentisic Acid Accessed through Slurry, Atomization Techniques, and Thermal Methods

Dyba,

Wiącek,

Nowak

et al. 2023

Crystal Growth & Design

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In this study, key features of metronidazole (MNZ) cocrystal polymorphs with gallic acid (GAL) and gentisic acid (GNT) were elucidated. Solvent-mediated phase transformation experiments in 30 solvents with varying properties were employed to control the polymorphic behavior of the MNZ cocrystal with GAL. Solvents with relative polarity (RP) values above 0.35 led to cocrystal I°, the thermodynamically stable form. Conversely, solvents with RP values below 0.35 produced cocrystal II, which was found to be only 0.3 kJ mol–1 less stable in enthalpy. The feasibility of electrospraying, including solvent properties and process conditions required, and spray drying techniques to control cocrystal polymorphism was also investigated, and these techniques were found to facilitate exclusive formation of the metastable MNZ-GAL cocrystal II. Additionally, the screening approach resulted in a new, high-temperature polymorph I of the MNZ-GNT cocrystal system, which is enantiotropically related to the already known form II°. The intermolecular energy calculations, as well as the 2D similarity between the MNZ-GAL polymorphs and the 3D similarity between MNZ-GNT polymorphs, rationalized the observed transition behaviors. Furthermore, the evaluation of virtual cocrystal screening techniques identified molecular electrostatic potential calculations as a supportive tool for coformer selection.

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Impurity-induced acceleration of polymorphic conversion via crystalline solid solutions and the T–X phase diagrams of salicylic acid and 3-hydroxybenzoic acid

Zhang,

Ricci,

Molajafari

et al. 2024

CrystEngComm

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The trimorphism of 3-hydroxybenzoic acid: an experimental and computational study

Abstract: Following the computational prediction that 3-hydroxybenzoic acid (3HBA) could exist in more than the two literature polymorphs, an experimental investigation targeting computationally generated structures was performed. The third polymorph III,...

Cited by 4 publications

References 47 publications

Searching for Suitable Kojic Acid Coformers: From Cocrystals and Salt to Eutectics

Searching for Suitable Kojic Acid Coformers: From Cocrystals and Salt to Eutectics

Metronidazole Cocrystal Polymorphs with Gallic and Gentisic Acid Accessed through Slurry, Atomization Techniques, and Thermal Methods

Impurity-induced acceleration of polymorphic conversion via crystalline solid solutions and the T–X phase diagrams of salicylic acid and 3-hydroxybenzoic acid

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