Ester hydrolysis: Conditions for acid autocatalysis and a kinetic switch

Bánsági, Tamás; Taylor, Annette F.

doi:10.1016/j.tet.2017.05.049

Cited by 21 publications

(17 citation statements)

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“…Investigating the dissolution of inorganic nanoparticles is a topic of great relevance, both theoretical and practical, with applications ranging from advanced materials to environmental science and medicine [ 1 , 2 , 3 , 4 ]. Cyclic esters are slow acid generators, useful for controlling the evolution of pH in time due to the acids produced by their hydrolysis [ 5 ]. As such, they are important tools for the application of systems chemistry principles to materials science [ 6 , 7 ].…”

Section: Introductionmentioning

confidence: 99%

“…As slow acid generators, we chose a lactone, δ-gluconolactone (GL), and a sultone, 1,3-propanesultone (PrS). The kinetics of hydrolysis of both are already known, and their reaction with water (Equations (1) and (2)) give, respectively, gluconic acid (pK a 3.86, a typical carboxylic acid) [ 5 ] and 1-hydroxypropanesulfonic acid (pK a 1.53, a typical sulfonic acid) [ 10 ], which are both strong enough to dissolve zinc oxide, thus forming the corresponding soluble salts (Equations (1) and (2)):…”

Section: Introductionmentioning

confidence: 99%

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Dissolution of Zinc Oxide Nanoparticles in the Presence of Slow Acid Generators

et al. 2022

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We describe a preliminary investigation of the dissolution dynamics of zinc oxide nanoparticles in the presence of cyclic esters (δ-gluconolactone and propanesultone) as slow acid generators. The particles dissolution is monitored by means of turbidimetry and correlated with the evolution of pH over time. The results could be of interest for the design of chemically programmable colloidal systems.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Dissolution of Zinc Oxide Nanoparticles in the Presence of Slow Acid Generators

et al. 2022

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“…Of course, the cleavage reaction itself consists of multiple steps, none of which is overtly catalytic [5]. The mechanisms by which Mn 2+ catalyzes the oxidation of oxalate by permanganate in this classical example of autocatalysis is much less obvious and can be explained only by an elaborate network of reactions [6,7].…”

Section: Introductionmentioning

confidence: 99%

Defining Autocatalysis in Chemical Reaction Networks

Andersen¹,

Flamm²,

Merkle³

et al. 2021

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Autocatalysis is a deceptively simple concept, referring to the situation that a chemical species X catalyzes its own formation. From the perspective of chemical kinetics, autocatalysts show a regime of superlinear growth. Given a chemical reaction network, however, it is not at all straightforward to identify species that are autocatalytic in the sense that there is a sub-network that takes X as input and produces more than one copy of X as output. The difficulty arises from the need to distinguish autocatalysis e.g. from the superposition of a cycle that consumes and produces equal amounts of X and a pathway that produces X. To deal with this issue, a number of competing notions, such as exclusive autocatalysis and autocatalytic cycles, have been introduced. A closer inspection of concepts and their usage by different authors shows, however, that subtle differences in the definitions often makes conceptually matching ideas difficult to bring together formally. In this contribution we make some of the available approaches comparable by translating them into a common formal framework that uses integer hyperflows as a basis to study autocatalysis in large chemical reaction networks. As an application we investigate the prevalence of autocatalysis in metabolic networks.

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“…This pH change can be made transient by coupling the MGS clock with an in situ acid generator such as a lactone 26 (Table S1, ESI †). 14,27 Lactones are the cyclic esters of carboxylic acids, with an enhanced tendency toward hydrolysis driven by the release of ring strain. 28 Among lactones, d-gluconolactone (GL) has risen to the forefront thanks to its non-toxicity, water solubility, availability, and the relatively low pK a (3.86) of its hydrolysis product, gluconic acid.…”

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confidence: 99%