References

  1. M.S. Latha, J. Martis, V. Shobhav, R.S. Shinde, S. Bangera, B. Krishnankutty, S. Bellary, S. Varughese, P. Rao, B.R.N. Kumar, Sunscreening agents: a review, J. Clin. Aesthet. Dermatol., 6 (2013) 16–26.
  2. A.J.M. Santos, M.S. Miranda, J.C.G.E. da Silva, The degradation products of UV filters in aqueous and chlorinated aqueous solutions, Water Res., 46 (2012) 3167–3176.
  3. S. Kim, K. Choi, Occurrences, toxicities, and ecological risks of benzophenone-3, a common component of organic sunscreen products: a mini-review, Environ Int., 70 (2014) 143–157.
  4. M.E. Balmer, H.R. Buser, M.D. Müller, T. Poiger, Occurrence of some organic UV filters in wastewater, in surface waters, and in fish from Swiss lakes, Environ. Sci. Technol., 39 (2005) 953–962.
  5. C.A. Downs, E. Kramarsky-Winter, R. Segal, J. Fauth, S. Knutson, O. Bronstein, F.R. Ciner, J. Rina, Y. Lichtenfeld, C.M. Woodley, P. Pennington, K. Cadenas, A. Kushmaro, Y. Loya, Toxicopathological effects of the sunscreen UV filter, oxybenzone (benzophenone-3), on coral planulae and cultured primary cells and its environmental contamination in Hawaii and the U.S. Virgin Islands, Arch. Environ. Contam. Toxicol., 70 (2015) 265–288.
  6. G. Kerdivel, R.L. Guevel, D. Habauzit, F. Brion, S. Ait-Aissa, F. Pakdel, Estrogenic potency of benzophenone UV filters in breast cancer cells: proliferative and transcriptional activity substantiated by docking analysis, PLoS One, 8 (2013) e60567.
  7. M. Coronado, H. De Haro, X. Deng, M.A. Rempel, R. Lavado, D. Schlenk, Estrogenic activity and reproductive effects of the UV-filter oxybenzone (2-hydroxy-4-methoxyphenylmethanone) in fish, Aquat. Toxicol., 90 (2008) 182–187.
  8. M. Schlumpf, S. Durrer, O. Faass, C. Ehnes, M. Fuetsch, C. Gaille, M. Henseler, L. Hofkamp, K. Maerkel, S. Reolon, B. Timms, J.A.F. Tresguerres, W. Lichtensteiger, Developmental toxicity of UV filters and environmental exposure: a review, Int. J. Androl., 31 (2008) 144–151.
  9. K.M. Hanson, E. Gratton, C.J. Bardeen, Sunscreen enhancement of UV-induced reactive oxygen species in the skin, Free Radical Biol. Med., 41 (2006) 1205–1212.
  10. D. Nakajima, S. Asada, S. Kageyama, T. Yamamoto, H. Kuramochi, N. Tanaka, K. Takeda, S. Goto, Activity related to the carcinogenicity of plastic additives in the benzophenone group, J. UOEH, 28 (2006) 143–156.
  11. H. Zhao, D. Wei, M. Li, Y. Du, Substituent contribution to the genotoxicity of benzophenone-type UV filters, Ecotoxicol. Environ. Saf., 95 (2013) 241–246.
  12. M.C. Cuquerella, V. Lhiaubet-Vallet, J. Cadet, M.A. Miranda, Benzophenone photosensitized DNA damage, Acc. Chem. Res., 45 (2012) 1558–1570.
  13. S.J. In, S.-H. Kim, R.E. Go, K.A. Hwang, K.-C. Choi, Benzophenone-1 and nonylphenol stimulated MCF-7 breast cancer growth by regulating cell cycle and metastasis-related genes via an estrogen receptor α-dependent pathway, J. Toxicol. Environ. Health, 78 (2015) 492–505.
  14. S.-H. Kim, K. Hwang, S.-M. Shim, K.-C. Choi, Growth and migration of LNCaP prostate cancer cells are promoted by triclosan and benzophenone-1 via an androgen receptor signaling pathway, Environ. Toxicol. Pharmacol., 39 (2015) 568–576.
  15. P.P. Phiboonchaiyanan, K. Busaranon, C. Ninsontia, P. Chanvorachote, Benzophenone-3 increases metastasis potential in lung cancer cells via epithelial to mesenchymal transition, Cell Biol. Toxicol., 33 (2017) 251–261.
  16. S. Zhang, X. Wang, H. Yang, Y.F. Xie, Chlorination of oxybenzone: kinetics, transformation, disinfection byproducts formation, and genotoxicity changes, Chemosphere, 154 (2016) 521–527.
  17. A. Gackowska, M. Przybyłek, W. Studziński, J. Gaca, Formation of chlorinated breakdown products during degradation of sunscreen agent 2-ethylhexyl-4-methoxycinnamate in the presence of sodium hypochlorite, Environ. Sci. Pollut. Res., 23 (2016) 1886–1897.
  18. J. Li, L.-Y. Ma, L. Xu, Transformation of benzophenone-type UV filters by chlorine: kinetics, products identification and toxicity assessments, J. Hazard. Mater., 311 (2016) 263–272.
  19. S.E. Duirk, D.R. Bridenstine, D.C. Leslie, Reaction of benzophenone UV filters in the presence of aqueous chlorine: kinetics and chloroform formation, Water Res., 47 (2013) 579–587.
  20. N. Negreira, P. Canosa, I. Rodrıguez, M. Ramil, E. Rubı, R. Cela, Study of some UV filters stability in chlorinated water and identification of halogenated by-products by gas chromatography–mass spectrometry, J. Chromatogr., A, 1178 (2008) 206–214.
  21. O. Acevedo, Simulating chemical reactions in ionic liquids using QM/MM methodology, J. Phys. Chem. A, 118 (2014) 11653−11666.
  22. G. Groenhof, Introduction to QM/MM Simulations, L. Monticelli, E. Salonen (eds.), Biomolecular Simulations: Methods and Protocols, Methods in Molecular Biology, Chap. 3, Vol. 924, Springer Science+Business Media, New York, 2013, pp. 43–65.
  23. M.W. van der Kamp, A.J. Mulholland, Combined quantum mechanics/molecular mechanics (QM/MM) methods in computational enzymology, Biochemistry, 16 (2013) 2708–2728.
  24. H.M. Senn, W. Thiel, QM/MM methods for biomolecular systems, Angew. Chem. Int. Ed. Engl., 48 (2009) 1198–1229.
  25. A.S. Gonçalves, T.C.C. França, J.D. Figueroa-Villar, P.G. Pascutti, Molecular dynamics simulations and QM/MM studies of the reactivation by 2-PAM of Tabun-inhibited human acethylcolinesterase, J. Braz. Chem. Soc., 22 (2011) 155–165.
  26. K.W. Sattelmeyer, J. Tirado-Rives, W.L. Jorgensen, Comparison of SCC-DFTB and NDDO-based semiempirical molecular orbital methods for organic molecules, J. Phys. Chem. A, 50 (2006) 13551–13559.
  27. M.P. Repasky, J. Chandrasekar, W. Jorgensen, PDDG/PM3 and PDDG/MNDO: improved semiempirical methods, J. Comput. Chem., 23 (2002) 1601–1622.
  28. S. Antonczak, M. Ruiz-López, J.-L. Rivail, The hydrolysis mechanism of formamide revisited: comparison between ab initio, semiempirical and DFT results, J. Mol. Model., 3 (1997) 434–442.
  29. J.J. Dannenberg, Hydrogen bonds: a comparison of semiempirical and ab initio treatments, J. Mol. Struct. THEOCHEM, 401 (1996) 279–286.
  30. H.F. Ridgway, B. Mohan, X. Cui, K.J. Chua, M.R. Islam, Molecular dynamics simulation of gas-phase ozone reactions with sabinene and benzene, J. Mol. Graphics Modell., 74 (2017) 241–250.
  31. G.B. Rocha, R.O. Freire, A.M. Simas, J.P. Stewart, RM1: a reparameterization of AM1 for H, C, N, O, P, S, F, Cl, Br, and I, J. Comput. Chem., 27 (2006) 1101–1111.
  32. W.L. Jorgensen, J. Chandrasekhar, J.D. Madura, R.W. Impey, M.L. Klein, Comparison of simple potential functions for simulating liquid water, J. Chem. Phys., 79 (1983) 926–935.
  33. P. Pulay, Convergence acceleration of iterative sequences: the case of SCF iteration, Chem. Phys. Lett., 73 (1980) 393–398.
  34. P. Pulay, Improved SCF convergence acceleration, J. Comput. Chem., 3 (1982) 556–560.
  35. A.S. Christensen, T. Kubar, Q. Cui, M. Elstner, Semiempirical quantum mechanical methods for noncovalent interactions for chemical and biochemical applications, Chem. Rev., 116 (2016) 5301−5337.
  36. M.S. Elioff, J. Hoy, J.A. Bumpus, Calculating heat of formation values of energetic compounds: a comparative study, Adv. Phys. Chem., 2016 (2016) 1–11.
  37. R. Casadesús, M. Moreno, A. González-Lafont, J.M. Lluch, M.P. Repasky, Testing electronic structure methods for describing intermolecular H...H interactions in supramolecular chemistry, J. Comput. Chem., 25 (2004) 99–105.
  38. I. Tubert-Brohman, C.R. Guimarães, M.P. Repasky, W.L. Jorgensen, Extension of the PDDG/PM3 and PDDG/MNDO semiempirical molecular orbital methods to the halogens, J. Comput. Chem., 25 (2004) 138–150.
  39. I.V. Alabugin, T.A. Zeidan, Stereoelectronic effects and general trends in hyperconjugative acceptor ability of σ-bonds, J. Am. Chem. Soc., 124 (2002) 3175–3185.
  40. I.V. Alabugin, K.M. Gilmore, P.W. Peterson, Hyperconjugation, WIREs Comput. Mol. Sci., 1 (2011) 109–141.
  41. K. Bozorov, J.-U. Zhao, H.A. Aisa, Recent advances in ipsonitration reactions, Archive Organ. Chem., Part I (2017) 41–66.
  42. T. Ohe, T. Mashino, M. Hirobe, Substituent elimination from p-substituted phenols by cytochrome P450: ipso-substitution by the oxygen atom of the active species, Drug Metab. Dispos., 25 (1996) 116–122.
  43. B. Kolvenbach, N. Schlaich, Z. Raoui, J. Prell, S. Zuhlke, A. Schaffer, F.P. Guengerich, P.F.X. Corvini, Degradation pathway of bisphenol A: does ipso substitution apply to phenols containing a quaternary alpha-carbon structure in the para position?, Appl. Environ. Microbiol., 73 (2007) 4776–4784.
  44. F.L. Gabriel, M. Cyris, G.W. Kohler, Ipso-substitution: a general biochemical and biodegradation mechanism to cleave alphaquaternary alkylphenols and bisphenol A, Chem. Biodivers., 9 (2007) 2123–2137.
  45. A. Fischer, G. Henderson, Bromination of phenols, isomerization and disproportionation of bromophenols, and dienone-phenol rearrangement of bromodienones, Can. J. Chem., 61 (1983) 1045–1053.
  46. Y. Ogata, M. Kimura, Y. Kondo, H. Katoh, F.-C. Chen, Orientation in the chlorination of phenol and of anisole with sodium and t-butyl hypochlorites in various solvents, J. Chem. Soc., Perkin Trans. 1, 2 (1984) 451–453.
  47. J.J. Mullins, Hyperconjugation: a more coherent approach, J. Chem. Educ., 89 (2012) 834–836.
  48. R.K. Bansal, N. Gupta, S. Bansal, Semiempirical PM3 calculations of pyridinium dichlorophosphinomethylides: presence of negative hyperconjugation, Indian J. Chem., Sect B, 43B (2004) 144–148.
  49. B. Galabova, G. Kolevaa, S. Simova, B. Hadjieva, H.F. Schaefer, P.V.R. Schleyer, Arenium ions are not obligatory intermediates in electrophilic aromatic substitution, Proc. Natl. Acad. Sci. U.S.A., 111 (2014) 10067–10072.
  50. T. Manasfi, V. Storck, S. Ravier, C. Demelas, B. Coulomb, J.-L. Boudenne, Degradation products of benzophenone‑3 in chlorinated seawater swimming pools, Environ. Sci. Technol., 49 (2015) 9308−9316.
  51. J.F. Bunnet, Physical organic terminology, after ingold, Bull. Hist. Chem., 19 (1996) 33−42.
  52. J.J.P. Stewart, Optimization of parameters for semiempirical methods V: modification of NDDO approximations and application to 70 elements, J. Mol. Model., 13 (2007) 1173–1213.
  53. J. Dolenc, J. Koller, An improved semiempirical MO PM3 method for hydrogen-bonded systems, Acta Chim. Slov., 53 (2006) 229–237.
  54. E.O. Igbinosa, E.E. Odjadjare, V.N. Chigor, I.H. Igbinosa, A.O. Emoghene, F.O. Ekhaise, N.O. Igiehon, O.G. Idemudia, Toxicological profile of chlorophenols and their derivatives in the environment: the public health perspective, Sci. World J., 2013 (2013) 1–11.
  55. J. Michałowicz, I. Majsterek, Chlorophenols, chlorocatechols and chloroguaiacols induce DNA base oxidation in human lymphocytes (in vitro), Toxicology, 268 (2010) 171–175.
  56. S. Rosokha, J.K. Kochi, The preorganization step in organic reaction mechanisms: charge transfer complexes as precursors to electrophilic aromatic substitutions, J. Org. Chem., 67 (2002) 1727–1737.