Hydrogen‐Bonded Complexes of Phenols

Laurence, Christian; Berthelot, M.; Graton, Jérôme

doi:10.1002/9780470682531.pat0284

Cited by 4 publications

(8 citation statements)

References 264 publications

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“…The pK HB scale developed by Taft focuses on equilibrium constants for H-bonded donor-acceptor complexes in solution. On this scale the H-bond acceptors relevant to this work have the following values; thiophene (−0.37), 20a methoxybenzene (−0.08), 22 nitrobenzene (+0.48), pyrazine (+1.22) and pyridine (+1.86). 20a This indicates that thiophene and methoxybenzene are poor H-bond acceptors in relation to the N-heterocyclic rings such as pyrazine and pyridine.…”

Section: Discussionmentioning

confidence: 99%

Syntheses of, and structural studies on, benzo-fused 1,2,4-thiadiazines

et al. 2014

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Section: Discussionmentioning

confidence: 99%

Syntheses of, and structural studies on, benzo-fused 1,2,4-thiadiazines

et al. 2014

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“…These observations are in accordance with the data from the CSD on carboxylic acids, where in the absence of competing hydrogen bond donors or acceptors, the carboxylic acid moiety will preferentially form the homodimer supramolecular synthon (Table ). Similarly, the phenolic substituents exhibit the common motifs associated with phenols such as the phenol O–H···O phenol homosynthon or the phenol O–H···OC acid heterosynthon. − A notable observation is that as the number of phenolic substituents on the phenolic acid backbone increases, other hydrogen bonding synthons characteristic of the phenol functional group become more prevalent, and all the phenolic substituents are involved in hydrogen bonding. For example, a higher number of hydrates are seen for gallic acid ( 1 ) and protocatechuic acid ( 2 ) which have three and two phenolic substituents, respectively.…”

Section: Polyphenolsmentioning

confidence: 99%

Cocrystallization of Nutraceuticals

Sinha

Maguire

Lawrence

2015

Crystal Growth & Design

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Cocrystallization has emerged over the past decade as an attractive technique for modification of the physicochemical properties of compounds used as active pharmaceutical ingredients (APIs), complementing more traditional methods such as salt formation. Nutraceuticals, with associated health benefits and / or medicinal properties, are attractive as coformers due to their ready availability, known pharmacological profile and natural origin, in addition to offering a dual therapy approach. Successful studies of favorably altering the physicochemical properties of APIs through cocrystallization with nutraceuticals are highlighted in this review. Many of the key functional groups commonly seen in nutraceuticals (e.g. acids, phenols), underpin robust supramolecular synthons in crystal engineering. This review assesses the structural data available to date across a diverse range of nutraceuticals, both in pure form and in multicomponent materials, identifies the persistent supramolecular features present. This insight will ultimately enable predictive and controlled assembly of functional materials incorporating nutraceuticals together with APIs.

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“…32,40 This observation is in accordance with the data from the CSD on carboxylic acids, 41 where in the absence of competing hydrogen bond acceptors, the carboxylic acid moiety will preferentially form the homodimer. Likewise, the phenolic substituent exhibits the common motifs associated with phenols, 33 i.e. O-H⋯OC acid heterosynthon in SA, and phenol O-H⋯O alcohol homosynthon in the methanol solvate.…”

Section: Structural Analysismentioning

confidence: 99%

“…Thus, they can hydrogen bond with acceptors such as pyridines and the oxygen atom of various carbonyl functional groups, as well as with donors including alcohols and other phenols. 33 The calculated molecular electrostatic potentials (MEPs) of the carboxylic acid (+246 kJ mol −1 ) and the phenolic (+218 kJ mol −1 ) moieties on sinapic acid also highlight the hydrogen-bond donor potential of sinapic acid. 15 Therefore, we anticipated that sinapic acid would form a range of intermolecular interactions such as acid-acid, acid-amide, acid-N aromatic , phenol-N aromatic and phenol-carbonyl hydrogen bonds, as illustrated in Fig.…”

Section: Introductionmentioning

confidence: 96%

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Novel co-crystals of the nutraceutical sinapic acid

et al. 2015

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Sinapic acid (SA) is a nutraceutical with known anti-oxidant, anti-microbial, anti-inflammatory, anti-cancer, and anti-anxiety properties. Novel co-crystals of SA were prepared with co-formers belonging to the category of GRAS [isonicotinic acid (INC), nicotinamide (NIA)], non-GRAS [4-pyridinecarbonitrile (PYC)], and active pharmaceutical ingredients (APIs) [6-propyl-2-thiouracil (PTU)] list of compounds. Structural study based on the X-ray crystal structures revealed the intermolecular hydrogen-bonded interactions and molecular packing. The crystal structure of sinapic acid shows the anticipated acid-acid homodimer along with discrete hydrogen bonds between the acid carbonyl and the phenolic moiety. The robust acid-acid homodimer appears to be very stable and is retained in the structures of two co-crystals (SA[middle dot]NIA and SA[middle dot]PYC). In these cases, co-crystallization occurs via intermolecular phenol O-H[three dots, centered]Naromatic hydrogen bonds between the co-formers. In the SA[middle dot]PTU[middle dot]2MeCN co-crystal the acid-acid homodimer gives way to the anticipated acid-amide heterodimer, with the phenolic moiety of SA hydrogen-bonded to acetonitrile. Attempts at obtaining the desolvated co-crystal led to lattice breakdown, thus highlighting the importance of acetonitrile in the formation of the co-crystal. Among the co-crystals examined, SA[middle dot]INC (5 weeks), SA[middle dot]NIA (8 weeks) and SA[middle dot]PYC (5 weeks) were found to be stable under accelerated humidity conditions (40 [degree]C, 75% RH), whereas SA[middle dot]PTU[middle dot]2MeCN decomposed after one week into individual components due to solvent loss

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Hydrogen‐Bonded Complexes of Phenols

Abstract: Introduction Hydrogen‐Bond Basicity of Phenols Hydrogen‐Bond Acidity of Phenols Self‐Association of Phenols Intramolecular Hydrogen Bonds Properties of the Complexes Construction of Hydrogen‐Bond Basicity Scalesfrom Phenols Hydrogen Bonding and Protonation

Cited by 4 publications

References 264 publications

Syntheses of, and structural studies on, benzo-fused 1,2,4-thiadiazines

Syntheses of, and structural studies on, benzo-fused 1,2,4-thiadiazines

Cocrystallization of Nutraceuticals

Novel co-crystals of the nutraceutical sinapic acid

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