Stability and cooperativity of hydrogen bonds in dihydroxybenzoic acids

Adam, Martin; Gutmann, Matthias J.; Leech, Charlotte K.; Middlemiss, Derek S.; Parkin, Andrew; Thomas, Lynne H.; Wilson, Chick C.

doi:10.1039/b9nj00353c

Cited by 29 publications

(25 citation statements)

References 32 publications

(23 reference statements)

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“…In order to facilitate the identification of the solid phases, a literature review of the previous reported structures is presented in the Supporting information (Table S3). From a single crystal, it was found that the gentisic acid crystalizes in monoclinic P system with cell parameters of a = 5.58 Å, b = 4.90 Å, c = 23.51 Å, β = 93.34°, which are comparable to those published in CCDC database (CCDC numbers: 747937-747942 and 747946-747948) [61].…”

Section: Solid Phase Studiessupporting

confidence: 72%

Solubility and solid phase studies of isomeric phenolic acids in pure solvents

Vilas-Boas

Brandão

Martins

et al. 2018

Journal of Molecular Liquids

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The solubilities of gallic, protocatechuic, gentisic or α-resorcylic acids were measured in nine pure solvents (water, methanol, ethanol, 1-propanol, 2-propanol, 2-butanone, ethyl acetate, acetonitrile and dimethylformamide) at 298.15 K and 313.15 K, using the analytical isothermal shake-flask method. Additionally, solid phase studies of the selected phenolic acids were carried out using differential scanning calorimetry (DSC) and X-ray diffraction (XRD), giving access to important data on melting properties as well as on the structure of the solid phase before and after the dissolution. The NRTL-SAC model coupled to the reference solvent approach (RSA) were applied to correlate the solubility data in a set of seven solvents and, after used to predict the solubility in 1-propanol and dimethylformamide. Average relative deviations (ARD) between 28 and 40% for the correlation and between 16 and 59% for the predictions were obtained. These values are within the order of magnitude usually found for such type of semipredictive models, using a limited set of data.

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Section: Solid Phase Studiessupporting

confidence: 72%

Solubility and solid phase studies of isomeric phenolic acids in pure solvents

Vilas-Boas

Brandão

Martins

et al. 2018

Journal of Molecular Liquids

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“…For the triclinic anhydrate, only the lattice dimensions have been reported, and the volume of ZZZEEU corresponds to a monohydrate rather than an anhydrous form(9) but not to the new monohydrate described in this work. For the monoclinic polymorph (form II° hereafter), the temperature range has been extended very recently down to 20 K.(10) Furthermore, different hydrate stoichiometries, ranging from 0.5 to 3 mol water per mol of acid can be found in literature reports, 8,11 but only the crystal structure of the hemihydrate has been determined. A recent study comparing six isomeric dihydroxybenzoic acids failed to crystallize new polymorphs by melt crystallization and sublimation experiments.…”

Section: Introductionmentioning

confidence: 99%

Solid-State Forms of β-Resorcylic Acid: How Exhaustive Should a Polymorph Screen Be?

Braun

Karamertzanis

Arlin

et al. 2010

Crystal Growth & Design

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A combined experimental and computational study was undertaken to establish the solid-state forms of β-resorcylic acid (2,4-dihydroxybenzoic acid). The experimental search resulted in nine crystalline forms: two concomitantly crystallizing polymorphs, five novel solvates (with acetic acid, dimethyl sulfoxide, 1,4-dioxane, and two with N,N-dimethyl formamide), in addition to the known hemihydrate and a new monohydrate. Form II°, the thermodynamically stable polymorph at room temperature, was found to be the dominant crystallization product. A new, enantiotropically related polymorph (form I) was obtained by desolvation of certain solvates, sublimation experiments, and via a thermally induced solid−solid transformation of form II° above 150 °C. To establish their structural features, interconversions, and relative stability, all solid-state forms were characterized with thermal, spectroscopic, X-ray crystallographic methods, and moisture-sorption analysis. The hemihydrate is very stable, while the five solvates and the monohydrate are rather unstable phases that occur as crystallization intermediates. Complementary computational work confirmed that the two experimentally observed β-resorcylic acid forms I and II° are the most probable polymorphs and supported the experimental evidence for form I being disordered in the p-OH proton position. These consistent outcomes suggest that the most practically important features of β-resorcylic acid crystallization under ambient conditions have been established; however, it appears impractical to guarantee that no additional metastable solid-state form could be found.

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“…Additionally, although feasible, without an initial X-ray model it is rather hard to determine crystal structures from the neutron diffraction, due to the positive and negative nature of the scattering lengths, which further complicates the assignment of phases. However, once obtained, neutron diffraction data give valuable information about absolute atomic positions and bond lengths especially involving hydrogen [68][69][70][71].…”

Section: Neutron Diffractionmentioning

confidence: 99%

X-ray and Neutron Diffraction in the Study of Organic Crystalline Hydrates

Fucke

Steed

2010

Water

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A review. Diffraction methods are a powerful tool to investigate the crystal structure of organic compounds in general and their hydrates in particular. The laboratory standard technique of single crystal X-ray diffraction gives information about the molecular conformation, packing and hydrogen bonding in the crystal structure, while powder X-ray diffraction on bulk material can trace hydration/dehydration processes and phase transitions under non-ambient conditions. Neutron diffraction is a valuable complementary technique to X-ray diffraction and gives highly accurate hydrogen atom positions due to the interaction of the radiation with the atomic nuclei.Although not yet often applied to organic hydrates, neutron single crystal and neutron powder diffraction give precise structural data on hydrogen bonding networks which will help explain why hydrates form in the first place.

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Stability and cooperativity of hydrogen bonds in dihydroxybenzoic acids

Cited by 29 publications

References 32 publications

Solubility and solid phase studies of isomeric phenolic acids in pure solvents

Solubility and solid phase studies of isomeric phenolic acids in pure solvents

Solid-State Forms of β-Resorcylic Acid: How Exhaustive Should a Polymorph Screen Be?

X-ray and Neutron Diffraction in the Study of Organic Crystalline Hydrates

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