The Volumetric Oxidation of Iodide and Bromide by Periodic Acid<sup>1</sup>

Willard, H. H.; Greathouse, Lucien H.

doi:10.1021/ja01279a010

Cited by 26 publications

(4 citation statements)

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“…Gravimetry is usually based on the formation of less soluble salts, such as barium periodate or paraperiodate. − Photospectroscopy relies on photoactivity, which was first reported by MacDonald and co-workers, and which was utilized by Crouthamel to confirm the dissociation constants . Further analysis methods are conductometry and potentiometry. , Structural assignments were achieved by Raman or infrared spectroscopy, and by single-crystal X-ray diffraction. − Modern analytical protocols were developed by Potthast and Waldvogel using high performance liquid chromatography coupled to a photodiode array (LC-PDA).…”

Section: Periodatementioning

confidence: 99%

Synthesis and Applications of Periodate for Fine Chemicals and Important Pharmaceuticals

Arndt

Kohlpaintner

Donsbach

et al. 2022

Org. Process Res. Dev.

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An emerging interest for the application of periodate in the synthesis of active pharmaceutical ingredients (APIs) and for the valorization of renewable feedstock is eminent. However, periodate exhibits a high molecular mass, is expensive compared to other common bulk-oxidizers and is used only reluctantly in technical applications. Recently, a new and green electrochemical synthesis was established. The preparation and regeneration method for periodate lowers costs and enables the use of periodate in the synthesis of regulated products. This review will briefly introduce the key innovations in the electrochemical synthesis of periodate and will survey the most important applications of periodate in the production of fine chemicals.

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Section: Periodatementioning

confidence: 99%

Synthesis and Applications of Periodate for Fine Chemicals and Important Pharmaceuticals

Arndt

Kohlpaintner

Donsbach

et al. 2022

Org. Process Res. Dev.

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“…The partially methylated acid was isolated and methylated with Purdie's reagent (20). The resultant ~nethylated ester glycoside (180 g) was dissolved in tetrahydrofuran (50 ml) and reduced by the dropwise addition with stirring of a solution of lithium aluminum hydride (600 ml) in tetrahydrofuran (23 ml).…”

Section: Proof Of Strzicture Of the Aldobiouronic :Lcidsmentioning

confidence: 99%

“…Oxidation was allowed to proceed in the dark a t 20". The periodate uptake was deterinined by the method of Willard and Greathouse (20) but using phosphate in place of borate and the formic acid production by the method of Halsall, Hirst, and Jones (21). …”

Section: Periodate Oxidation Of the Undegraded Polysaccharidementioning

confidence: 99%

The Structure of the "Gum Asafoetida" Polysaccharide

Jones¹,

Thomas²

1961

Can. J. Chem.

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The polysaccharide from gum asafoetida contains D-galactose, I>-arabinose, L-rhamnose, 4-O-methyl-~-glucuro11ic acid, and D-glucuronic acid. I t is a highly branched polyn~er which contains a backbone of D-galactopyranose residues which are very probably n~aiilly 1,3-Plinked.The side chains consist of residues of L-arabiiiofuranose, ~-g a l a~t~p y r a l l o~e , D-glucuronic acid, and its 4-0-methyl ether.

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“…Periodate is a powerful oxidizing agent in dilute aqueous solutions, and therefore, it has long been the subject of studies of elaborating different analytical procedures. , The majority of these methods is based on the direct oxidation of iodide and bromide ions by periodate producing elementary halogens that interact with the species to be analyzed quantitatively by different methods. For example, it has been shown that trace amounts of arsenic, thiocyanate, and phenylhydrazine and micro amounts of bromide and iodide ions can conveniently and precisely be determined by these methods.…”

Section: Introductionmentioning

confidence: 99%

Kinetics and Mechanism of the Oxidation of Bromide by Periodate in Aqueous Acidic Solution

2014

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The periodate–bromide reaction has been studied spectrophotometrically mainly in excess of bromide ion, monitoring the formation of the total amount of bromine at 450 nm at acidic buffered conditions and at a constant ionic strength in the presence of a phosphoric acid/dihydrogen phosphate buffer. The stoichiometry of the reaction was established to be strictly IO4(–) + 2Br(–) + 2H(+) → Br2 + IO3(–) + H2O. The formal kinetic order of the reactants was found to be perfectly one and two in the cases of periodate and bromide, respectively, but that of the hydrogen ion lies between one and two. We have also provided experimental evidence that dihydrogen phosphate accelerates the formation of bromine, suggesting the appearance of strong buffer assistance. On the basis of the experiments, a simple two-step kinetic model is proposed involving BrIO3 as a key intermediate that perfectly explains all of the experimental findings. Furthermore, we have also shown that in huge excess of bromide, the apparent rate coefficient obtained from the individual curve fitting method of the absorbance–time series is necessarily independent of the initial periodate concentration that may falsely be interpreted as the rate of bromine formation is also independent of the concentration of periodate.

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The Volumetric Oxidation of Iodide and Bromide by Periodic Acid¹

Cited by 26 publications

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Synthesis and Applications of Periodate for Fine Chemicals and Important Pharmaceuticals

Synthesis and Applications of Periodate for Fine Chemicals and Important Pharmaceuticals

The Structure of the "Gum Asafoetida" Polysaccharide

Kinetics and Mechanism of the Oxidation of Bromide by Periodate in Aqueous Acidic Solution

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The Volumetric Oxidation of Iodide and Bromide by Periodic Acid1

Cited by 26 publications

References 0 publications

Synthesis and Applications of Periodate for Fine Chemicals and Important Pharmaceuticals

Synthesis and Applications of Periodate for Fine Chemicals and Important Pharmaceuticals

The Structure of the "Gum Asafoetida" Polysaccharide

Kinetics and Mechanism of the Oxidation of Bromide by Periodate in Aqueous Acidic Solution

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Product

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The Volumetric Oxidation of Iodide and Bromide by Periodic Acid¹