Citation: Mengdie Cai, Weimin Gan, Zhiqin Ding, Hongping Cai, Lijun Wei, Xianglei Cheng. Studies on reaction mechanisms and distinct chemiluminescence from cyanoimino neonicotinoids triggered by peroxymonosulfate in advanced oxidation processes[J]. Chinese Chemical Letters, ;2023, 34(3): 107554. doi: 10.1016/j.cclet.2022.05.068 shu

Studies on reaction mechanisms and distinct chemiluminescence from cyanoimino neonicotinoids triggered by peroxymonosulfate in advanced oxidation processes

Jiangxi Province Key Laboratory of Preventive Medicine, School of Public Health, Nanchang University, Nanchang 330006, China

weilj7681@163.com

chengxlsd@163.com

Received Date: 7 February 2022
Revised Date: 7 May 2022
Accepted Date: 21 May 2022
Available Online: 26 May 2022

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In this study, we proposed a novel method to investigate the advanced oxidation process of neonicotinoids (NNIs) from the perspective of concomitant chemiluminescence (CL) reaction. It was found that in the presence of cobalt ions with cyanoimino NNIs, acetamiprid (ACE) and thiacloprid (THI), could promote peroxymonosulfate and Ru(bpy)₃²⁺ to produce strong CL, but no CL occurred with nitro-involved NNIs as alternatives. Experimental dada from UV absorption spectra and chemiluminescence spectra suggested that new cyclic compounds might be formed during the reaction. Based on the results of free radical scavenging experiment and mass spectra, a new degradation and reaction mechanism of cyanoimino-containing NNIs was proposed. ACE or THI were first attacked by SO₄^•− to form benzyl radicals, which in turn reacted with the carbon atoms of cyano group through electrophilic addition reaction in the formation of intramolecular ring. Then a redox reaction between Ru(bpy)₃³⁺ and imino group immediately took place with CL emission (610 nm). The new mechanistic knowledge would be meaningful for other contaminants for their interactions with PMS.
- Advanced oxidation processes,
- Chemiluminescence mechanisms,
- Annulation reaction,
- Peroxymonosulfate,
- Acetamiprid,
- Thiacloprid
1. [1]
  W.C. Yu, L.X. Zhao, Trac. Trends Anal. Chem. 136 (2021) 116197. doi: 10.1016/j.trac.2021.116197
2. [2]
  Z. Lin, W. Xue, H. Chen, J.M. Lin, Anal. Chem. 83 (2011) 8245–8251. doi: 10.1021/ac202039h
3. [3]
  B. Al Mughairy, H.A.J. AlLawati, Trac. Trends Anal. Chem. 124 (2020) 115802. doi: 10.1016/j.trac.2019.115802
4. [4]
  M.W. Yang, J.G. Huang, J.L. Fan, et al., Chem. Soc. Rev. 49 (2020) 6800–6815. doi: 10.1039/D0CS00348D
5. [5]
  Y. Zhang, R. Zhang, X.L. Yang, H.L. Qi, C.X. Zhang, J. Pharm. Anal. 9 (2019) 9–19. doi: 10.1016/j.jpha.2018.11.004
6. [6]
  Z.X. Zhan, Y.C. Dai, Q.Y. Li, Y. Lv, Trac. Trends Anal. Chem. 134 (2021) 116129. doi: 10.1016/j.trac.2020.116129
7. [7]
  X.N. Dou, Q. Zhang, S.N.A. Shah, et al., Chem. Sci. 10 (2019) 497–500. doi: 10.1039/C8SC03511C
8. [8]
  S.N.A. Shah, X.N. Dou, M. Khan, K. Uchiyama, J.M. Lin, Talanta 196 (2019) 370–375. doi: 10.1016/j.talanta.2018.12.091
9. [9]
  W. Xue, Z. Lin, H. Chen, C. Lu, J.M. Lin, J. Phys. Chem. C 115 (2011) 21707–21714. doi: 10.1021/jp207554t
10. [10]
  W.W. Cheng, X. Teng, C. Lu, Anal. Chem. 92 (2020) 5456–5463. doi: 10.1021/acs.analchem.0c00204
11. [11]
  L.J. Zhang, M.N. Shi, W.J. Zhou, W.J. Guan, C. Lu, Anal. Chem. 93 (2021) 7724–7731. doi: 10.1021/acs.analchem.1c01136
12. [12]
  L. Mi, Y.D. Sun, L. Shi, T. Li, ACS Appl. Mater. Interfaces 12 (2020) 7879–7887. doi: 10.1021/acsami.9b18053
13. [13]
  Z. Lin, W. Xue, H. Chen, J.M. Lin, Chem. Commun. 48 (2012) 1051–1053. doi: 10.1039/C1CC15290D
14. [14]
  J. Liu, H. Chen, Z. Lin, J.M. Lin, Anal. Chem. 82 (2010) 7380–7386. doi: 10.1021/ac101510b
15. [15]
  K.L. James, N.P. Randall, K.F.A. Walters, N.R. Haddaway, M. Land, Environ. Evid. 5 (2016) 1–9. doi: 10.1186/s13750-016-0052-0
16. [16]
  D.D. Zhang, S.X. Cui, Z.P. Xu, D.M. Li, Z.Z. Tian, Chin. Chem. Lett. 28 (2017) 1743–1745. doi: 10.1016/j.cclet.2017.05.002
17. [17]
  C.C. Zhu, G.L. Li, K.Y. Xiao, et al., Chin. Chem. Lett. 30 (2019) 255–258. doi: 10.1016/j.cclet.2018.05.013
18. [18]
  R. Meffe, I. d. Bustamante, Sci. Total Environ. 481 (2014) 280–295. doi: 10.1016/j.scitotenv.2014.02.053
19. [19]
  A. Jelic, M. Gros, A. Ginebreda, et al., Water Res. 45 (2011) 1165–1176. doi: 10.1016/j.watres.2010.11.010
20. [20]
  E.A.D. Mitchell, B. Mulhauser, M. Mulot, et al., Science 358 (2017) 109–111. doi: 10.1126/science.aan3684
21. [21]
  K. Tasman, S.A. Rands, J.J.L. Hodge, iScience 23 (2020) 1–17.
22. [22]
  C.A. Hallmann, R.P. Foppen, C.A. Van Turnhout, H. De Kroon, E. Jongejans, Nature 511 (2014) 341–352. doi: 10.1038/nature13531
23. [23]
  J. Babelova, Z. Sefcikova, S. Cikos, et al., Toxicology 392 (2017) 71–80. doi: 10.1016/j.tox.2017.10.011
24. [24]
  A. Osaka, J. Ueyama, T. Kondo, et al., Environ. Res. 147 (2016) 89–96. doi: 10.1016/j.envres.2016.01.028
25. [25]
  D. Guo, S. You, F. Li, Y. Liu, Chin. Chem. Lett. 33 (2022) 1–10. doi: 10.1016/j.cclet.2021.06.027
26. [26]
  Y. Zhang, B.T. Zhang, Y.G. Teng, et al., J. Hazard. Mater. 400 (2020) 123290. doi: 10.1016/j.jhazmat.2020.123290
27. [27]
  J. Qi, J. Liu, F. Sun, et al., Chin. Chem. Lett. 32 (2021) 1814–1818. doi: 10.1016/j.cclet.2020.11.026
28. [28]
  C. Lyu, L. Zhang, D. He, B. Su, Y. Lyu, Chin. Chem. Lett. 33 (2022) 930–934. doi: 10.1016/j.cclet.2021.07.012
29. [29]
  L.W. Matzek, K.E. Carter, Chemosphere 151 (2016) 178–188. doi: 10.1016/j.chemosphere.2016.02.055
30. [30]
  F. Rehman, M. Sayed, J.A. Khan, et al., J. Hazard. Mater. 357 (2018) 506–514. doi: 10.1016/j.jhazmat.2018.06.012
31. [31]
  L. Chen, T. Cai, C. Cheng, Z. Xiong, D. Ding, Chem. Eng. J. 351 (2018) 1137–1146. doi: 10.1016/j.cej.2018.06.107
32. [32]
  S. Zhou, Y. Wang, K. Zhou, et al., Chin. Chem. Lett. 32 (2021) 2179–2182. doi: 10.1016/j.cclet.2020.12.002
33. [33]
  B. Lin, X. Lu, N. Li, N. Xu, J.M. Lin, Chin. Chem. Lett. 31 (2020) 476–478. doi: 10.1016/j.cclet.2019.07.066
34. [34]
  Y. Zheng, Z. Wu, J.M. Lin, L. Lin, Chin. Chem. Lett. 31 (2020) 451–454. doi: 10.1016/j.cclet.2019.07.036
35. [35]
  X. Cui, X. Liu, C. Lin, M. He, W. Ouyang, Chemosphere 254 (2020) 126820. doi: 10.1016/j.chemosphere.2020.126820
36. [36]
  M.M. Du, H.N. Kuang, Y.Q. Zhang, et al., J. Environ. Chem. Eng. 9 (2021) 105647. doi: 10.1016/j.jece.2021.105647
37. [37]
  J. Tan, Z.F. Li, J. Li, et al., J. Hazard. Mater. 423 (2022) 127048. doi: 10.1016/j.jhazmat.2021.127048
38. [38]
  S. Banerjee, S. Sathyamoorthi, J. Du Bois, R.N. Zare, Chem. Sci. 8 (2017) 7003–7008. doi: 10.1039/C7SC02240A
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