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; Friesen, Brent; Bohinski, Tim; Bulger, David; Federici, Matthew; Hale, Jenny; Mancinelli, Jenna; Mirza, Khalid B.; Moritz, Marshall; Rein, Daniel T.; Tchakounte, Cedric; Truong, Hai Bang

doi:10.1038/npre.2010.4243

Cited by 9 publications

(7 citation statements)

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“…Although to our best knowledge there lacks literature value of OA solubility in the two solvents, the 10-fold better solubility of 1-otadecylamine, the saturated version of oleylamine, in toluene than hexane is in line with our hypothesis. 33 This increased solubility caused the OA molecules that were originally attached to the AuNPs to gradually detach from the AuNPs, which is supported by our observations in poor AuNP stability and surface-pressure isotherms ( Figure 6). Understandably, amines form weaker bonds with gold than thiols, thus resulting in a higher tendency to detach.…”

Section: ' Results and Discussionsupporting

confidence: 76%

Enhanced Ordering in Gold Nanoparticles Self-Assembly through Excess Free Ligands

et al. 2011

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Self-assembly of nanometer-sized particles is an elegant and economical approach to achieve dense patterns over large areas beyond the resolution and throughput capabilities of electron-beam lithography. In this paper, we present results of self-assembly of oleylamine-capped gold nanoparticles with 8.0 ± 0.3 nm diameter into densely packed and well-ordered monolayers with center-to-center distance of ∼11 nm. Self-assembly was done in a Langmuir-Blodgett trough and picked up onto Si substrates. The nanoparticles undesirably assembled within micrometer-sized "droplets" that were organic in nature. However, within these droplets, we observed that the addition of the excess ligand, oleylamine, drastically enhanced the self-assembly of the nanoparticles into monolayers with near-perfect ordering. This approach has the potential use in templated self-assembly of nanoparticles for rearranging poorly ordered assembly into a commensurate prepatterned substrate.

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Section: ' Results and Discussionsupporting

confidence: 76%

Enhanced Ordering in Gold Nanoparticles Self-Assembly through Excess Free Ligands

et al. 2011

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“…To compare calculated solubilities, we drew on the Open Notebook Science Solubility Challenge 24 which provides 9700 experimental solubility datasets, where in their terminology, a “dataset” 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 sub-set based on four rules.…”

Section: Methodsmentioning

confidence: 99%

“…Data for our test comes from the Open Notebook Challenge. 24 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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“…Cheminformaticians will recognize this data structure as an edge from graph theory. This structure allows us to represent facts like "vanillin dissolves in methyl alcohol" [7]. RDF uses Uniform Resource Identifiers (URIs) to identify things.…”

Section: Conceptsmentioning

confidence: 99%