Determination of Diaryliodonium Cation by Reverse Iodometric Titration with Ascorbic Acid

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F22%3A43925016" target="_blank" >RIV/60461373:22310/22:43925016 - isvavai.cz</a>

Result on the web

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DOI - Digital Object Identifier

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Result language

angličtina

Original language name

Determination of Diaryliodonium Cation by Reverse Iodometric Titration with Ascorbic Acid

Original language description

Today, diaryliodonium salts have found numerous of applications in organic synthesis, covalent activation of carbon surfaces by arylation, as additives in livestock feed mixtures, as initiators of polymerization reactions or they are being studied for theirs promising use in pharmacy as a NADH dehydrogenase inhibitor. For the analysis of the diaryliodonium salts, the authors in the literature use HPLC with subsequent detection by MS or UV/Vis, as well as 1H and 13C NMR. X-ray diffraction can also be used for crystalline analysis. Using these methods, the presence or amount of the resulting substance can be determined, and by NMR or X-ray diffraction the structure of the resulting product can also be verified. However, these methods are instrumentally demanding and are not always available in the facility. On the other hand, this may be volumetric titration. In general, a titration is a widely used analytical method for routine determination of analyte content in both laboratory and industrial samples. It is usually not very demanding on instrumentation, and it can be easily automated. Compared to NMR and HPLC, it usually allows more precise determination of the substance contend. Its disadvantages include a lower sensitivity threshold and non-selectivity to similar reactants (depending on the type of detection). Therefore, titration is of course not able to replace HPLC or NMR in terms of elucidation of the specific structure of the analyte (NMR) or multiple product analysis. However, no titration method taking advantage of the oxidising ability of diaryliodonium salts can be found in the literature. This is slightly surprising since diaryliodonium compounds belong to a group of hypervalent iodine compounds, which are well known oxidation agents. In this work, the very first titration method for the determination of diaryliodonium salts is presented. The developed reverse titration is based on reaction of diaryliodonium salt with excess of ascorbic acid which is, in the next step, determined by means of iodometric potentiometric titration. This titration was investigated in terms of the effect pH, reaction time or the excess of ascorbic acid used for reduction. These conditions were implemented in the developed method. Subsequently, the method was tested on different derivatives of diaryliodonium salts. Despite being applicable to wide range of diaryliodonium salts, the procedure is not universal, and it failed in some cases. These cases are also discussed. The determination error and its possible causes are also discussed. The work was supported from European Regional Development Fund-Project “Organic redox couple based batteries for energetics of traditional and renewable resources (ORGBAT)” No. CZ.02.1.01/0.0/0.0/16_025/0007445.

Czech name

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Czech description

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Type

O - Miscellaneous

CEP classification

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OECD FORD branch

10406 - Analytical chemistry

Project

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Continuities

O - Projekt operacniho programu

Publication year

2022

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů