Open Notebook Science Challenge: Solubilities of Organic Compounds in Organic Solvents

Bradley, Jean‐Claude; Neylon, Cameron; Guha, Rajarshi; Williams, Antony J.; Hooker, Bill; Lang, Andrew S.; Friesen, Brent; Bohinski, Tim; Bulger, David A; Federici, Matthew; Hale, Jenny; Mancinelli, Jenna; Mirza, Khalid B.; Moritz, Marshall; Rein, Daniel T.; Tchakounte, Cedric; Truong, Hai T.

doi:10.1038/npre.2010.4243.3

Cited by 10 publications

(7 citation statements)

References 6 publications

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“…To demonstrate that COSMotherm handles vanillin reasonably well, we also calculated the solubility of solid vanillin in nine solvents based on the enthalpy H melt (5.35 kcal/mol) and temperature (355 K) of melting. 10 The predictions show good agreement with experiment (Table 1). …”

Section: ■ Discussionsupporting

confidence: 58%

Comment on “Phase Behavior of Ternary Mixtures of Water–Vanillin–Ethanol for Vanillin Extraction via Dissipative Particle Dynamics”

et al. 2015

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This comment addresses a few issues of concern regarding the use of Dissipative Particle Dynamics (DPD) to characterize molecular phase diagrams and identify phase morphologies in the recent paper by Son et al. (J. Chem. Eng. Data 2014, 59, 3036−3040). While useful solubility modeling and self-assembly can be aided by various coarse graining strategies including DPD, one should employ as well complementary techniques and ensure consistency of conclusions through experiments or readily available tools. We believe the approach and parametrization scheme is inappropriate to the system of study resulting in unrealistic results and interpretations.

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Section: ■ Discussionsupporting

confidence: 58%

Comment on “Phase Behavior of Ternary Mixtures of Water–Vanillin–Ethanol for Vanillin Extraction via Dissipative Particle Dynamics”

et al. 2015

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“…Data Set Selection. To compare calculated solubilities, we drew on the Open Notebook Science Solubility Challenge 25 which provides 9700 experimental solubility data sets, where in their terminology, a "data set" consists of a set of experimental data resulting in a solubility measurement. We wanted a test set consisting of around 50 solubility measurements, so we filtered these 9700 measurements to select a subset based on four rules.…”

Section: Methodsmentioning

confidence: 99%

“…Data for our test comes from the Open Notebook Challenge. 25 For each of these solute−solvent pairs, we compute the solvation free energy and other properties, allowing us to calculate the relative solubility for comparison with experiment.…”

Section: Introductionmentioning

confidence: 99%

Using MD Simulations To Calculate How Solvents Modulate Solubility

Liu¹,

Cao²,

Hoang³

et al. 2016

J. Chem. Theory Comput.

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Here, our interest is in predicting solubility in general, and we focus particularly on predicting how the solubility of particular solutes is modulated by the solvent environment. Solubility in general is extremely important, both for theoretical reasons – it provides an important probe of the balance between solute-solute and solute-solvent interactions – and for more practical reasons, such as how to control the solubility of a given solute via modulation of its environment, as in process chemistry and separations. Here, we study how the change of solvent affects the solubility of a given compound. That is, we calculate relative solubilities. We use MD simulations to calculate relative solubility and compare our calculated values with experiment as well as with results from several other methods, SMD and UNIFAC, the latter of which is commonly used in chemical engineering design. We find that straightforward solubility calculations based on molecular simulations using a general small-molecule force field outperform SMD and UNIFAC both in terms of accuracy and coverage of the relevant chemical space.

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“…A central goal in chemistry is to understand and manipulate molecular properties through the addition of chemical substituents at particular sites on the molecule. − Recently, strong-field ionization and mass spectrometry have been employed to assess the effects of substituent groups on molecular properties such as cationic excited state energies, vibrational couplings, and dissociation dynamics. − In fluoro- and methoxy-substituted phenols, the substitution pattern on the phenyl ring was found to determine the adiabatic ionization energy and vibrational energy levels . Time-resolved experiments and quantum calculations for trifluoroacetone and trichloroacetone revealed enhanced dissociation when the delay between the pump and probe pulses matched the vibrational dynamics of the respective molecules, with the longer vibrational period of trichloroacetone correlating with a longer time delay producing the maximum fragmentation yield .…”

Section: Introductionmentioning

confidence: 99%

Controlling Dissociation of Alkyl Phenyl Ketone Radical Cations in the Strong-Field Regime through Hydroxyl Substitution Position

et al. 2014

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The hydroxy-substituted alkyl phenyl ketones 2'-, 3'- and 4'- (ortho, meta, and para) hydroxyacetophenone were excited in the strong-field regime with wavelengths ranging from 1200-1500 nm to produce the respective radical cations. For 2'- and 3'-hydroxyacetophenone, the parent molecular ion dominated the mass spectrum, and the intensity of the fragment ions remained unchanged as a function of excitation wavelength. In contrast, 4'-hydroxyacetophenone exhibited depletion of the parent molecular ion with corresponding enhanced formation of the benzoyl fragment ion upon excitation with 1370 nm as compared with other excitation wavelengths. Density functional (DFT) calculations suggest that dissociation occurs when the acetyl group in 4'-hydroxyacetophenone radical cation twists out-of-plane with respect to the phenyl ring, enabling a one-photon transition between the ground cation state D0 and the excited cation state D2 to occur. The DFT calculations also suggest that the lack of dissociation in the wavelength-resolved strong-field excitation measurements for 2'- and 3'-hydroxyacetophenone arises because both isomers have a barrier to rotation about the carbon-carbon bond connecting the phenyl and acetyl groups. These results help elucidate the effects of substituents on the torsional motion of radical cations and illustrate the potential for controlling molecular dissociation through the addition of substituents.

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Open Notebook Science Challenge: Solubilities of Organic Compounds in Organic Solvents

Cited by 10 publications

References 6 publications

Comment on “Phase Behavior of Ternary Mixtures of Water–Vanillin–Ethanol for Vanillin Extraction via Dissipative Particle Dynamics”

Comment on “Phase Behavior of Ternary Mixtures of Water–Vanillin–Ethanol for Vanillin Extraction via Dissipative Particle Dynamics”

Using MD Simulations To Calculate How Solvents Modulate Solubility

Controlling Dissociation of Alkyl Phenyl Ketone Radical Cations in the Strong-Field Regime through Hydroxyl Substitution Position

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