Effect of Intramolecular Donor-Acceptor Interactions on the Radiolysis of Organic Compounds: Effects in Acetylacetone

• Published in: Doklady. Physical chemistry (1991) Vol. 510; no. 2; pp. 91 - 94
• Main Authors: Vlasov, S. I., Ponomarev, A. V., Ershov, B. G.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01-06-2023; Springer Nature B.V
• Subjects: Acetylacetone; Chemistry; Chemistry and Materials Science; Hydrogen bonds; Organic compounds; Pentanone; Physical Chemistry; Radiolysis; acetylacetone; tautomers; proton transfer; radical recombination; hydrogen bond; radiolysis
• ISSN: 0012-5016; 1608-3121
• DOI: 10.1134/S0012501622600188

It has been shown for acetylacetone as an example that the intramolecular hydrogen bond significantly affects the radiolytic transformations of organic compounds by suppressing the proton transfer from the primary radical cation to the molecule and also by promoting cleavage of the C–OH bond in the enol form. Due to these effects, the major heavy product of radiolysis at 295 K is 4-oxopent-2-en-2-yl acetate. Under boiling conditions (413 K), hydrogen bonds are cleaved, resulting in the predominant formation of 4-hydroxy-2-pentanone, which is not detected at 295 K.