Spectral-Luminescent Study of the Acid–Base Equilibrium of 5-Aminouracil and 6-Aminouracil in Aqueous Solutions

S. S. Ostakhov; Остахов С. С.; R. R. Kayumova; Каюмова Р. Р.; A. A. Akhiyarov; Ахияров А. А.; S. P. Ivanov; Иванов С. П.; S. L. Khursan; Хурсан С. Л.

doi:10.31857/S0023119323010102

Spectral-Luminescent Study of the Acid–Base Equilibrium of 5-Aminouracil and 6-Aminouracil in Aqueous Solutions

Authors: Ostakhov S.S.¹, Kayumova R.R.¹, Akhiyarov A.A.¹, Ivanov S.P.¹, Khursan S.L.¹
Affiliations:
1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences
Issue: Vol 57, No 1 (2023)
Pages: 3-8
Section: PHOTONICS
URL: https://rjeid.com/0023-1193/article/view/661525
DOI: https://doi.org/10.31857/S0023119323010102
EDN: https://elibrary.ru/DCKNTA
ID: 661525

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Abstract
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Abstract

The spectral fluorescence characteristics of 5-aminouracil (5AU) and 6-aminouracil (6AU) in neutral and alkaline aqueous solutions have been studied. With the use of the density functional theory, it has been shown that uracils preferentially dissociate at the N1–H bond. The acid–base equilibrium constants pKa1(5AU) = 9.4 and pKa1(6AU) = 8.95 were determined by a fluorescence method. It was concluded that the ultrashort lifetime of the excited singlets of 5AU and 6AU prevents the measurement of the acid–base equilibrium constant of uracils in an electronically excited state.

Keywords

6-aminouracil, 5-aminouracil, fluorescence, acid–base equilibrium, pKa1

References

Watson J.D., Crick F.H.C. // Nature. 1953. V. 171. № 4361. P. 964.
Sowers L.C., Shaw B.R, Veigl M.L., Sedwick W.D. // Mutat. Res. 1987. V. 177. P. 201.
Abdrakhimova G.S., Ovchinnikov M.Yu., Lobov A.N., Spirikhin L.V., Ivanov S.P., Khursan S.L. // J. Phys. Org. Chem. 2014. V. 27. P. 876.
Abdrakhimova G.S., Ovchinnikov M.Yu., Lobov A.N., Spirikhin L.V., Khursan S.L., Ivanov S.P. // J. Mol. Struct. 2018. V. 1158. P. 51.
Privat E.S., Sowers L.C. // Mutat. Res. 1996. V. 354. P. 151.
Wittenberg E. // Chem. Ber. 1966. V. 99. P. 2391.
Berens K., Shugar D. // Acta Biochim. Polonica. 1963. V. 10. № 1. P. 25.
Wempen I., Fox J.J. // J. Am. Chem. Soc. 1964. V. 86. № 12. P. 2474.
Ilyina M.G., Khamitov E.M., Ivanov S.P., Mustafin A.G., Khursan S.L. // J. Phys. Chem. A. 2017. V. 122. P. 341.
Ilyina M.G., Khamitov E.M., Ivanov S.P., Khursan S.L. // Comput. Theor. Chem. 2016. V. 1078. P. 81.
Zielenkiewicz W., Poznanski J., Zielenkiewicz A. // J. Solution Chem. 2000. V. 29. P. 757.
Ахияров А.А., Иванов С.П. // Вестник Башкирского университета. 2021. Т. 26. С. 631.
Ostakhov S.S., Sultanbaev M.V., Ovchinnikov M.Yu., Kayumova R.R., Khursan S.L. // High Energy Chem. 2017. V. 51. P. 108.
Ivanov S.P., Ostakhov S.S., Abdrakhimova G.S., Akhiyarov A.A., Khursan S.S. // Biophys. Chem. 2020. V. 266. 106432.
Паркер С. Фотолюминесценция растворов / Под ред. Васильева Р.Ф. М.: Мир, 1972. 510 с.
Tatischeff I., Klein K. // Photochem. Photobiol. 1975. V. 22. P. 221.
Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Scalmani G., Barone V., Mennucci B., Petersson G.A., Nakatsuji H., Caricato M., Li X., Hratchian H.P., Izmaylov A.F., Bloino J., Zheng G., Sonnenberg J.L., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery Jr. J. A., Peralta J.E., Ogliaro F., Bearpark M., Heyd J.J., Brothers E., Kudin K.N., Staroverov V.N., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J.C., Iyengar S.S., Tomasi J., Cossi M., Rega N., Millam J.M., Klene M., Knox J.E., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Martin R.L., Morokuma K., Zakrzewski V.G., Voth G.A., Salvador P., Dannenberg J.J., Dapprich S., Daniels A.D., Farkas Ö., Foresman J.B., Ortiz J.V., Cioslowski J., Fox D.J. // Gaussian 09, Revision D.1, Gaussian, Inc., Wallingford CT. 2009.
Andrienko G.A. // Chemcraft. Version 1.8 (build 489). URL: http://www.chemcraftprog.com.
Tao J., Perdew J.P., Staroverov V.N., Scuseria G.E. // Phys. Rev. Lett. 2003. V. 91. 146401.
Krishnan R., Binkley J.S., Seeger R., Pople J.A. // J. Chem. Phys. 1980. V. 72. P. 650.
Tomasi J., Mennucci B., Cammi R. // Chem. Rev. 2005. V. 105. P. 2999.
Bányász Á., Karpati S., Mercier Ya., Reguero M., Gustavsson T., Markovitsi D., Improta R. // J. Phys. Chem. B. 2010. V. 114. P. 12708.
Jimenez-Halla J.O.C., Matito E., Robles J., Sola M. // J. Organomet. Chem. 2006. V. 691. № 21. P. 4359.
Stanger A. // J. Org. Chem. 2005. V. 71. № 3. P. 883.
Gustavsson T., Improta R., Bányász Á., Vaya I., Markovitsi D. // J. Photochem. Photobiol. A. 2012. V. 234. P. 37.
Васильев В.П. Аналитическая химия. Ч. 1. Гравиметрический и титриметрические методы анализа. М.: Высшая школа, 1989. 320 с.
Langen P., Etzold G., Barwolff D., Preussel B. // Biochem. Pharm. 1967. V. 16. P. 1833.
Stankevich E.I., Popelis Yu.Yu., Grinshtein E.E., Ozola A.Ya., Dubur G.Ya. // Khim. Geterot. Soed. 1970. V. 6. P. 122.
Barlin G.B. // J. Chem. Soc. B. 1971. P. 1425.
Hatada T., Mamori M., Nakashima K., Yoshimura M. // Yakugaku Zasshi. 1978. V. 98. № 5. P. 668.
Mori M., Teshima S., Yoshimoto H., Fujita S., Taniguchi R., Hatta H., Nishimoto S. // J. Phys. Chem. B. 2001. V. 105. № 10. P. 2070.
Барлтроп Дж., Койл Дж. Возбужденные состояния в органической химии / Под ред. Кузьмина М.Г. М.: Мир, 1978. 446 с.
Gustavsson T., Bányász Á., Lazzarotto E., Markovitsi D., Scalmani G., Frisch M.J., Barone V., Improta R. // J. Am. Chem. Soc. 2006. V. 128. № 2. P. 607.