Peculiarities in the Radiolysis of β-Diketones

S. I. Vlasov; Власов С. И.; A. A. Smirnova; Смирнова А. А.; A. V. Ponomarev; Пономарев А. В.; D. A. Uchkina; Учкина Д. А.; A. Yu. Sholokhova; Шолохова А. Ю.; A. A. Mitrofanov; Митрофанов А. А.

doi:10.31857/S0023119323030166

Peculiarities in the Radiolysis of β-Diketones

Authors: Vlasov S.I.¹, Smirnova A.A.², Ponomarev A.V.¹, Uchkina D.A.¹, Sholokhova A.Y.¹, Mitrofanov A.A.²
Affiliations:
1. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences
2. Faculty of Chemistry, Moscow State University
Issue: Vol 57, No 3 (2023)
Pages: 218-223
Section: RADIATION CHEMISTRY
URL: https://rjsvd.com/0023-1193/article/view/661508
DOI: https://doi.org/10.31857/S0023119323030166
EDN: https://elibrary.ru/KIFSPQ
ID: 661508

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Abstract

Intramolecular hydrogen bonding has a significant effect on the radiolytic transformations of β- diketones. Using the radiolysis of acetylacetone as an example, it has been shown that a hydrogen bond between the hydroxyl and carbonyl in an enol prevents proton transfer from the primary radical cation to the neighboring molecule. As a result, the radiolytic formation of a keto alcohol (4-hydroxy-2-pentanone) was not observed at room temperature, but it was effective under boiling conditions. The intramolecular hydrogen
bond contributed to a significant structural stress in the radical cation, which increased the yield of C–OH bond cleavage and the inhomogeneous formation of acetate (4-oxopent-2-en-2-yl acetate) under normal conditions

Keywords

дикетон, енол, ацетилацетон, радиолиз, водородная связь, фрагментация

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