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Direct and Indirect Photodegradation of Daidzein in Different Dissociated Forms in Water: Theoretical Analysis Based on DFT/TDDFT

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Abstract

Daidzein (DAID), as a common phytoestrogen, is often detected in the environment. In this paper, the photodegradation mechanism and UV absorption spectra of three different dissociation forms of DAID in water were studied by density functional theory (DFT) and time-dependent density functional theory (TDDFT). The photodegradation mechanism includes direct photolysis and indirect photolysis by reacting with ·OH in water. The reaction types of indirect photolysis of DAID0 with ·OH are OH-addition and H-abstraction, and H-abstraction is more favorable than OH-addition. The indirect photolysis reaction type of DAID− and DAID2− with ·OH is OH-addition. The degree of difficulty in the reaction of the three dissociation forms of DAID in water with ·OH is: DAID0 < DAID− < DAID2−. Results have shown that DAID can undergo degradation and can be transformed by reacting with ·OH in water. In addition, the direct photolysis reaction is also considered in the excited state to reveal the mechanism of the photochemical reaction. The direct photolysis pathway of DAID in water is the cleavage of C–C bond and C–O bond, but the Ea values required for these reactions are higher than the Ea values for the indirect photolysis reactions, indicating that direct photolysis is not the main pathway of photodegradation. The method of quantum chemical calculation in this study is helpful to understand the photochemical transformation of DAID in water.

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The dataset used and/or analyzed in this study are available from the corresponding author on reasonable request.

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Funding

This research was supported by the National Natural Science Foundation of China (41601519).

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Authors and Affiliations

  1. School of Environmental Science and Engineering, Collaborative Innovation Center of Atmospheric Environment and Equipment Technology, Jiangsu Key Laboratory of Atmospheric Environment Monitoring and Pollution Control, Nanjing University of Information Science and Technology, Nanjing, 210044, China

    Ying Lu, Yifan Shen & Se Wang

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  1. Ying Lu
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  2. Yifan Shen
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  3. Se Wang
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YL performed the theoretical calculations and wrote the manuscript; YS performed the data analyses and manuscript preparation; SW contributed to the conception of the study and wrote the manuscript.

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Correspondence to Se Wang.

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Lu, Y., Shen, Y. & Wang, S. Direct and Indirect Photodegradation of Daidzein in Different Dissociated Forms in Water: Theoretical Analysis Based on DFT/TDDFT. Water Air Soil Pollut 235, 62 (2024). https://doi.org/10.1007/s11270-023-06858-9

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