"Diketone - Enol" and "Enol - Enol" Tautomerism in Polyfluoroacyl Cycloalkanone Organic Compounds

Kuchkorova Raino Rasulovna; Iskandarov Aybek Yuldashevich

Authors

Kuchkorova Raino Rasulovna Candidate of Chemical Sciences, Associate Professor
Iskandarov Aybek Yuldashevich Tashkent State Pedagogical University named after Nizami

Keywords:

Diketone-enol, Enol-enol, NMR, CCl4, CDCl3, and DMFA-d7, CF3 Groups, Cis-enol, Trans-enol, 1,3-diketones

Abstract

The research investigates tautomers of polyfluoroacyl cycloalkanone structures while exploring how fluorine groups and cyclic ring systems affect their enol and diketone tautomerism. The research field of linear β-diketones has been thoroughly studied but investigational work on fluorinated cyclic analogs stays poorly understood. The analysis of tautomeric equilibria occurred through ¹H and ¹³C NMR and IR spectroscopy techniques which evaluated solvents such as CDCl₃, CCl₄, DMFA-d₇. Computer modeling through MINDO/3, MNDO/H, AM1, RMZ and Sybyl provided structural support. Results show that majority of 2-polyfluoroacyl cycloalkanones exist mainly as enols through strong intramolecular hydrogen bonding but 2-perfluorohexanoylcyclododecanone favors the diketone form because of its macrocyclic effects. IR spectral examinations demonstrated simultaneous existence of tautomers as well as chemical shift data supported electronic modifications from the CF₃ groups. The research discoveries create vital knowledge for understanding fluorinated systems that are utilized in drug design and catalysis applications and material science developments. The investigation of dynamic tautomerism requires more research to be done under physiological conditions while expanding studies to include metal-complexed derivatives and heterocyclic systems.

References

[1] R. R. Kuchkorova, “IK-i PMR–Spektr-Analiz 1-Benzoil-3-(4-Bromfenil)-5-Gidroksi-5-Triftormetil-2-Pirazolinovogo Liganda,” in Int. Sci. Res. Conf., vol. 3, no. 32, pp. 8–14, Mar. 2025.

[2] B. Umarov and R. Kuchkorova, “Complex Nickel (II) Compounds Based on Acylhydrazones of Aroyltrifluoracetylmethanes,” Science and Innovation, vol. 2, no. A12, pp. 236–241, 2023.

[3] B. F. Kurbonov, B. B. Umarov, and N. A. Parpiyev, “Spektroskopicheskoye issledovaniye kompleksov Ni(II), Zn(II), Co(II) s gidrazonami monokarbonilnykh soyedineniy,” Uzb. Khim. Zhurnal, no. 3, pp. 3–6, 1996.

[4] Sh. Z. Kadirova and R. R. Kuchkarova, “Preparation of Aliphatic and Aromatic 1,3-Diketones with Polyfluoroalkyl Substitutes,” Eur. Chem. Bull., no. 7, 2023.

[5] R. R. Kuchkarova, “Kompleksnye soyedineniya na osnove asilgidrazonov 1-(2-tenoil)-3,3,3-triftorasetona,” Nov. 2022.

[6] R. R. Kuchkarova, “Kompleksnye soyedineniya proizvodnykh ftorirovannykh β-diketonov s perekhodnymi metallami,” unpublished.

[7] U. B. Bafoevich, R. K. Rasulovna, and K. S. Ziyodulloevna, “Reaction of 1,1,1-Trifluoromethyl-4-Phenylbutanedione-2,4 with Benzoic Acid Hydrazide,” Inf. Technol. Ind., vol. 9, no. 3, pp. 939–944, 2021.

[8] R. R. Kuchkarova, “Kompleksnye soyedineniya sinka(II) na osnove asilgidrazonov 1-(tenoil)-3,3,3-triftorasetona,” Qo‘qon Davlat Ped. Inst. Ilmiy Xabarlari, no. 4, pp. 532–539, 2024.

[9] R. R. Kuchkorova, “Complex Nickel(II) Compounds Based on Acylhydrazones of Aroyltrifluoracetylmethanes,” Science and Innovation Int. Sci. J., pp. 236–241, 2023.

[10] R. R. Kuchkorova, “Kolchato-syepnykh peregruppirovkakh ligandov pri kompleksoobrazovanii s ionami perekhodnykh metallov,” Tafakkur Ziyosi, no. 1, pp. 158–161, 2024.

[11] B. B. Umarov, Kompleksnye soyedineniya nekotorykh perekhodnykh metallov s bis-5-oksipirazolinami, Dr. Sci. diss., Institute of Chemistry, Academy of Sciences of the Republic of Uzbekistan, Tashkent, 1996.

[12] R. R. Kuchkarova, “Asilgidrazony 1-(2-tenoil)-3,3,3-triftorasetona,” Ta’lim, Fan va Innovatsiya, no. 1, pp. 39–42, 2024.

[13] R. R. Kuchkorova, B. B. Umarov, and Sh. Z. Kadirova, “Preparation of Aliphatic and Aromatic 1,3-Diketones with Polyfluoroalkyl Substitute,” Eur. Chem. Bull., vol. 12, no. 7, pp. 303–307, 2023.

[14] B. B. Umarov, Kompleksnye soyedineniya nekotorykh perekhodnykh metallov s bis-5-oksipirazolinami, Dr. Sci. diss., Institute of Chemistry, Academy of Sciences of the Republic of Uzbekistan, Tashkent, 1996.

[15] R. R. Kuchkorova, B. B. Umarov, and Sh. Z. Kadirova, “Preparation of Aliphatic and Aromatic 1,3-Diketones with Polyfluoroalkyl Substitute,” Eur. Chem. Bull., vol. 12, no. 7, pp. 303–307, 2023.