INFLUENCE OF INTRAMOLECULAR DONOR-ACCEPTOR INTERACTIONS ON RADIOLYSIS OF ORGANIC COMPOUNDS: EFFECTS IN ACETYLACETONE-Reference-Cited by-同舟云学术

INFLUENCE OF INTRAMOLECULAR DONOR-ACCEPTOR INTERACTIONS ON RADIOLYSIS OF ORGANIC COMPOUNDS: EFFECTS IN ACETYLACETONE

Published:2023-05-01 Issue:1 Volume:510 Page:69-73
ISSN:2686-9535
Container-title:Доклады Российской академии наук. Химия, науки о материалах
language:
Short-container-title:Doklady Rossijskoj akademii nauk. Himiâ, nauki o materialah.

Author:

Vlasov S. I.¹,Ponomarev A. V.¹,Ershov B. G.¹

Affiliation:

1. A.N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences

Abstract

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

Publisher

The Russian Academy of Sciences

Reference11 articles.

1. Belova N.V., Oberhammer H., Trang N.H., Girichev G. V. // J. Org. Chem. 2014. V. 79. P. 5412–5419. https://doi.org/10.1021/jo402814c

2. Antonov I., Voronova K., Chen M.-W., Sztáray B., Hemberger P., Bodi A., Osborn D.L., Sheps L. // J. Phys. Chem. A. 2019. V. 123. P. 5472–5490. https://doi.org/10.1021/acs.jpca.9b04640

3. Imatdinova D.N., Vlasov S.I., Ponomarev A.V. // Mendeleev Commun. 2021. V 31. P. 558–560. https://doi.org/10.1016/j.mencom.2021.07.041

4. Howard D.L., Kjaergaard H.G., Huang J., Meuwly M. // J. Phys. Chem. A. 2015. V. 119. P. 7980–7990. https://doi.org/10.1021/acs.jpca.5b01863

5. Curran H.J. // Int. J. Chem. Kinet. 2006. V. 38. P. 250–275. https://doi.org/10.1002/kin.20153