Self-association of acetic acid in some organic solvents

Fujii, Yukio; Yamada, Hiromichi; Mizuta, Masateru

doi:10.1021/j100334a054

Cited by 126 publications

(152 citation statements)

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“…The stoichiometry of the fast pre-equilibrium deprotonation is 1:1, which means that the concentration of acetic acid is as high as the initial concentration of precatalyst complex 92. However, as acetic acid mainly exists as a hydrogen-bonded dimer in dichloromethane solution, [143] as well as at least two new species. In the presence of the azide, the deprotonation reaction of the alkyne substrate will be greatly favoured as the acetylide complex K02E reacts with the azide in a fast and irreversible elementary step, so that the concentration of K02E is steadily kept low.…”

Section: Variation Of Catalyst Concentrationmentioning

confidence: 99%

Highly Active Dinuclear Copper Catalysts for Homogeneous Azide–Alkyne Cycloadditions

et al. 2012

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It is better to light a candle than to curse the dark. AbstractThe copper-catalyzed azide-alkyne cycloaddition for the synthesis of 1,4-disubstituted 1,2,3-triazoles (CuAAC) is a variant of Huisgen's 1,3-dipolar cycloaddition which disburdens the thermal reaction from its major drawbacks such as poor regioselectivity, long reaction times and harsh conditions. In contrast to the widely used "black box" reagent mixtures, a molecularly defined, highly active catalyst system for homogeneous CuAAC reactions has been developed in this PhD project. In dependence on the postulated stepwise mechanism, its most important structural feature is the presence of two copper(I) ions irreversibly bound in the same catalyst molecule.A highly modular and profitable synthesis for bistriazolium hexafluorophosphate salts as precursors for the ancillary ligand system was devised. In analogy to the CuAAC catalyst systems of general formula [(NHC) 2 Cu]PF 6 described in literature, novel dinuclear copper(I) complexes with a bistriazolylidene ligand backbone and 1,3-bis(2,6-diisopropylphenyl)-imidazol-2-ylidene (IPr) as sacrificial ligand were prepared.However, these complexes did not show the expected high catalytic activity, most probably due to the strong coordination of the IPr ligands. In consequence, another family of dinuclear copper(I) complexes with m-coordinated acetate as labile ligand was synthesized by reaction of the bistriazolium hexafluorophosphate ligand precursors with copper(I) acetate in the presence of a base.The broad applicability and high catalytic activity of one of these bistriazolylidene dicopper acetate complexes was confirmed by a series of gaschromatographically mo-

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Section: Variation Of Catalyst Concentrationmentioning

confidence: 99%

Highly Active Dinuclear Copper Catalysts for Homogeneous Azide–Alkyne Cycloadditions

et al. 2012

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“…The formation of dimers is favored at increased acetic acid concentration. The selfassociation of acetic acid in some organic solvent has been studied by Fujii et al, 37 using FTIR spectroscopy and partition techniques. The FTIR peak assignment is not straight forward, as monomers and dimers are in constant equilibrium and most of the vibrations are coupled, but he proposed the following peak assignment for the carbonyl stretch: ϳ 1715 cm : terminal carbonyl.…”

Section: Molecular Interactionsmentioning

confidence: 99%

“…Acetic acid will, therefore, enhance water solubility. Fujii et al 37 studied the partition of benzoic acid between an aqueous phase and an organic solvent immiscible with water. These authors hypothesized the formation of water-bridged benzoic acid dimers in the organic phase.…”

Section: Molecular Interactionsmentioning

confidence: 99%

Diffusion of water-acetic acid mixtures in epoxy

Dutheillet

Mantle

Veselý

et al. 1999

J. Polym. Sci. B Polym. Phys.

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“…Homodimer formation has been observed for many different types of molecules, ranging from simple acetic acid [1] to highly complex proteins [2]. In particular, many kinds of proteins, such as the structural coat proteins of viruses [3,4], and functional enzymes, such as organophosphorous hydrolase [5], form homodimers.…”

Section: Introductionmentioning

confidence: 99%

Lock-and-key dimerization in dense Brownian systems of hard annular sector particles

Hodson

Mason

2016

Phys. Rev. E

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We develop a translational-rotational cage model that describes the behavior of dense two dimensional (2D) Brownian systems of hard annular sector particles (ASPs), resembling "C"-shapes. At high particle densities, pairs of ASPs can form mutually interdigitating lock-and-key dimers. This cage model considers either one or two mobile central ASPs which can translate and rotate within a static cage of surrounding ASPs that mimics the system's average local structure and density. By comparing with recent measurements made on dispersions of microscale lithographic ASPs (P.-Y. Wang and T.G. Mason, J. Am. Chem. Soc. 137 15308 (2015)), we show that mobile two-particle predictions of the probability of dimerization P dimer , equilibrium constant K, and 2D osmotic pressure Π2D, as a function of the particle area fraction φA, correspond closely to these experiments. By contrast, predictions based on only a single mobile particle do not agree well with either the two-particle predictions or the experimental data. Thus, we show that collective entropy can play an essential role in the behavior of dense Brownian systems composed of non-trivial hard shapes, such as ASPs.

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Self-association of acetic acid in some organic solvents

Cited by 126 publications

References 0 publications

Highly Active Dinuclear Copper Catalysts for Homogeneous Azide–Alkyne Cycloadditions

Highly Active Dinuclear Copper Catalysts for Homogeneous Azide–Alkyne Cycloadditions

Diffusion of water-acetic acid mixtures in epoxy

Lock-and-key dimerization in dense Brownian systems of hard annular sector particles

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