Abstract: 2-Methyl-9H-selenoxanthen-9-one (selenoxanthone) 1 was obtained by the reaction of bis-(2-carboxyphenyl)diselenide with toluene in concentrated sulphuric acid. It is demonstrated by means of cyclic voltammetry, EPR spectroscopy and quantum chemical DFT calculations that the electrochemical reduction (ECR) of selenoxanthone 1 in acetonitrile is a one-electron reversible process with the formation of a long-lived radical anion having a similar type of the highest occupied molecular orbital (HOMO) to the radical anions of the thioxanthone series. The ECR potential of selenoxanthone 1 is found to be less negative than the corresponding ECR potential of its related 2-methyl-9H-thioxanthen-9-one, which indicates an increase in the adiabatic electron affinity of selenoxanthone 1 compared to its sulphur-containing analogue. This fact confirms the general nature of the phenomenon of an increase in the adiabatic electron affinity of heterocyclic compounds when a heteroatom is replaced by a heavier one within group VIa of the periodic system of elements.

Cite: ODINTSOV D.S. , IRTEGOVA I.G. , OS'KINA I.A. , SHUNDRIN L.A.
SYNTHESIS AND ELECTROCHEMICAL REDUCTION OF 2-METHYL-9H-SELENOXANTHEN-9-ONE
ХИМИЯ В ИНТЕРЕСАХ УСТОЙЧИВОГО РАЗВИТИЯ. 2023. V.31. N6. P.652-658. DOI: 10.15372/CSD2023513 WOS РИНЦ

ArticleLinkType.TRANSLATED_TO_ORIGINAL: Одинцов Д.С. , Иртегова И.Г. , Оськина И.А. , Шундрин Л.А.
Синтез и электрохимическое восстановление 2-метил-9Н-селеноксантен-9-она
ХИМИЯ В ИНТЕРЕСАХ УСТОЙЧИВОГО РАЗВИТИЯ. 2023. №6. С.671-677. DOI: 10.15372/KhUR2023513 РИНЦ

Identifiers:

Web of science	WOS:001155665200001
Elibrary	59461430
OpenAlex	W4403854621

Altmetrics: