Статья
2020
Acidity Constants of Lignin Model Compounds in the Electronically Excited State in Water–N,N-Dimethylformamide Mixtures
M. V. Kuznetsova, D. S. Kosyakov, N. S. Gorbova, K. G. Bogolitsyn
Российский журнал физической химии А
https://doi.org/10.1134/S0036024420080178
Abstract / Full Text
The acidity constants of a number of guaiacyl phenols simulating structural fragments of natural lignins in the electronically excited state in water–N,N-dimethylformamide mixtures are determined by fluorescence spectroscopy using the Förster cycle. The differentiating effect of an aprotic solvent on the acidity of phenols is shown. It is found that the pKa values in the excited state are associated with the properties of para-substituents with respect to the phenolic hydroxyl group. The highest capacity for acid ionization during photoexcitation is exhibited by compounds containing an electron-withdrawing carbonyl group.
Author information
- Northern (Arctic) Federal University, 163002, Arkhangelsk, RussiaM. V. Kuznetsova, D. S. Kosyakov, N. S. Gorbova & K. G. Bogolitsyn
- Federal Center for Integrated Arctic Research, Russian Academy of Sciences, 163000, Arkhangelsk, RussiaN. S. Gorbova
References
- C. Heitner, D. Dimmel, and J. A. Smidt, Lignin and Lignans: Advances in Chemistry (CRC, Boca Ration, 2010).
- K. G. Bogolitsyn, V. V. Lunin, D. S. Kosyakov, A. P. Karmanov, et al., Physical Chemistry of Lignin (Akademkniga, Moscow, 2010) [in Russian].
- D. S. Kosyakov, N. S. Gorbova, K. G. Bogolitsyn, and L. V. Gusakov, Russ. J. Phys. Chem. A 81, 1076 (2007). https://doi.org/10.1134/S0036024407070126
- A. A. Freitas, C. P. Silva, G. T. M. Silva, et al., Photochem. Photobiol. 94, 1086 (2018). https://doi.org/10.1111/php.12944
- K. G. Bogolitsyn, N. S. Gorbova, and D. S. Kosyakov, Russ. J. Phys. Chem. A 77, 590 (2003).
- L. Yang, J. Niu, Y. Zhan, et al., Chin. J. Chem. 36, 42 (2017). https://doi.org/10.1002/cjoc.201700534
- G. Cilento and W. Adam, Free Radical Biol. Med. 19, 103 (1995). https://doi.org/10.1016/0891-5849(95)00002-F
- S. Liukko, V. Yasapuro, and T. Liitia, Holzforschung. 61, 509 (2007).https://doi.org/10.1515/HF.2007.107
- C. Jaeger, A. Nourmamode, and A. Castellan, Holzforschung. 47, 375 (1993). https://doi.org/10.1515/hfsg.1993.47.5.375
- D. S. Kosyakov, N. V. Ul’yanovskii, E. A. Anikeenko, and N. S. Gorbova, Rapid Commun. Mass Spectrom. 30, 2099 (2016).https://doi.org/10.1002/rcm.7686
- K. Radotic, A. Kalauzi, D. Djikanovic, et al., J. Photochem. Photobiol. B 83, 1 (2006).https://doi.org/10.1016/j.jphotobiol.2005.12.001
- B. Albinsson, L. Shiming, K. Lundquist, and R. Stomberg, J. Mol. Struct. 508, 19 (1999).https://doi.org/10.1016/S0022-2860(98)009132
- N. S. Gorbova, D. S. Kosyakov, and K. G. Bogolitsyn, Izv. Vyssh. Uchebn. Zaved., Zh. Lesn., No. 2, 129 (2010).
- M. Klessinger and J. Michl, Excited States and Photochemistry of Organic Molecules (VCH, Weinheim, 1995).
- J. R. Lakowich, Principles of Fluorescence Spectroscopy (Kluwer, New York, 1999).
- Q. Wang, Y. Niu, R. Wang, et al., Chem. Asian J. 13, 1735 (2018).https://doi.org/10.1002/asia.201800457
- T. Forster, Zeitschr. Electrochem. 54, 42 (1950). https://doi.org/10.1002/bbpc.19500540111
- N. S. Gorbova, Cand. Sci. (Chem.) Dissertation (Arkhangel’sk, 2002).
- S. R. Manohara, V. U. Kumar, Shivakumariaiah, and L. Gerward, J. Mol. Liq. 181, 97 (2013). https://doi.org/10.1016/j.molliq.2013.02.018
- C. Reichardt, Solvents and Solvent Effects in Organic Chemistry (Weinheim, Wiley-VCH, 2011).
- C. Reichardt, Chem. Rev. 94, 2319 (1994). https://doi.org/10.1021/cr00032a005
- M. Ravi, T. Soujanya, A. Samanta, and T. P. Radhakrishnan, J. Chem. Soc. Faraday Trans. 91, 2739 (1995). https://doi.org/10.1039/FT9959102739
- D. D. Thiare, A. Khnote, A. Diop, et al., J. Mol. Liq. 211, 640 (2015).https://doi.org/10.1016/j.molliq.2015.07.071
- B. Szczepanik, J. Mol. Struct. 1099, 209 (2015). https://doi.org/10.1016/j.molstruc.2015.05.062
- B. Valeur, Molecular Fluorescence. Principles and Application (Wiley-VCH, Weinheim, 2002).
- S. Tetteh, R. Zugle, J. Prosper Kwaku Adotey, and A. Quashie, J. Spectrosc. 2018, 4193657 (2018). doi 1155/2018/4193657