From the X-rays to a reliable “low cost” computational structure of caffeic acid: DFT, MP2, HF and integrated molecular dynamics–X-ray diffraction approach to condensed phases

Lombardo, Giuseppe M.; Portalone, Gustavo; Colapietro, Marcello; Rescifina, Antonio; Punzo, Francesco

doi:10.1016/j.molstruc.2011.03.001

Cited by 14 publications

(20 citation statements)

References 54 publications

(82 reference statements)

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“…1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 The structure of caffeic acid displays identical motifs to those observed in gallic acid and protocatechuic acid, wherein the expected acid-acid homodimer is retained with one of the phenolic substituents responsible for satisfying the carbonyl group of the acid-acid dimer on both sides (FESNOG01) (Figure 15). 65 The remaining phenolic substituent forms bifurcated hydrogen bonds with two phenolic substituents of an adjacent caffeic acid molecule. There are ten known crystal structures containing p-coumaric acid (see Table 1).…”

Section: Phenolic Acidsmentioning

confidence: 99%

“…The structure of caffeic acid (FESNOG01) 65. The structure of caffeic acid-nicotinamide (1:1) monohydrate also displays the preferred acid-amide heterodimer, where the two phenolic substituents of caffeic acid on adjacent molecules are involved in forming a R 2 2 (10) supramolecular homosynthon, thus giving rise to a 2-D sheet like architecture (MUPMOA)(Figure 16) 66.…”

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confidence: 99%

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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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Section: Phenolic Acidsmentioning

confidence: 99%

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confidence: 99%

Cocrystallization of Nutraceuticals

Sinha

Maguire

Lawrence

2015

Crystal Growth & Design

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“…The competition between these binding sites has been addressed by several studies. 1,[3][4][5]6,9,[20][21][22][23][24] Of the thirty-one hits that CA generates in the Cambridge Structural Database [(CSD (Conquest version 1.14 Build RC5)], none corresponds to a CA salt. In fact, the present literature reports, mainly, computational studies of these compounds 1,[3][4][5]9,24 or the attempts to characterize their structures in solution.…”

Section: Introductionmentioning

confidence: 99%

“…As QM driven MD schemes are quite computationally expensive, whenever QM effects can be neglected, empirical FF are preferred. 32 In a previous work 20 we performed a thorough comparison of QM and empirical FF applied to the study of CA. The reported results evidenced how the chosen empiric FF best reproduced, even if compared to the QM ones, the ab initio H-bonding and stacking stabilization energies.…”

Section: Introductionmentioning

confidence: 99%

Potassium caffeate/caffeic acid co-crystal: the rat race between the catecholic and carboxylic moieties in an atypical co-crystal

et al. 2012

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The vast literature concerning caffeic acid and its derivatives lacks any reference to the solid state structures of its inorganic salts as these crystals are quite difficult grow. Most of the already published works deal with computational studies of these compounds as well as investigations of their behaviour in solution. Having obtained good quality potassium caffeate/caffeic acid co-crystals, we solved their structure and used a robust approach, already applied to caffeic acid alone, to compare the X-ray structure with the one inferred by Molecular Dynamics (MD), focusing our attention on the structure-property relationships. The reliability of this method is confirmed by the overall agreement extended up to the anisotropic displacement parameters calculated, on one hand, by means of MD and the ones gathered, on the other hand, by X-ray measurements. Moreover, the lack of experimental evidence of an enthalpically favored polymorph, arising from the MD calculations, were explained on the basis of the Shannon's entropy.

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“…Experience has shown that upon a careful parametrisation, MD simulations can accurately reproduce crystal structures to the level of anisotropic displacement parameters. 67,68 Nevertheless, unless all relevant parameters are fine tuned, simulated results are better used in a qualitative man-ner, 67 as most force fields had proven to reproduce the overall behaviour of molecular systems reasonably well. [69][70][71] Free energy calculations are particularly sensitive to the choice of force field and parameters, and results are difficult to validate experimentally.…”

Section: Addressing the Validity Of Molecular Dynamics Simulationsmentioning

confidence: 99%

Investigating the hydration and structural changes of molecular organic materials under high-pressure conditions

Granero-García¹

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RMS root mean square Z N P T partition function, or RSS residual sum of squares number of molecules per unit cell s reduced coordinate xviii Database study on hydrate formation at high pressure Water is the most common solvent present in molecular organic materials, 9 and is easily incorporated in their structure due to its small size and H-bond forming capabilities. 10 Despite its ubiquitous presence and a considerable amount of research on the topic (Ch. 2), our understanding of the role of water in organic crystals is still limited, and prediction and control of hydrate formation remains an open question in crystal engineering. 11 A complete database study of hydrates formed at high pressure has been performed to bring to light trends on hydrate formation which can further contribute to systematise our overall knowledge on phase transformations. An equation of state for the compressibility of lattice water has been modelled as part of this study, providing an use-

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From the X-rays to a reliable “low cost” computational structure of caffeic acid: DFT, MP2, HF and integrated molecular dynamics–X-ray diffraction approach to condensed phases

Cited by 14 publications

References 54 publications

Cocrystallization of Nutraceuticals

Cocrystallization of Nutraceuticals

Potassium caffeate/caffeic acid co-crystal: the rat race between the catecholic and carboxylic moieties in an atypical co-crystal

Investigating the hydration and structural changes of molecular organic materials under high-pressure conditions

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