ORIGINAL RESEARCH
High Ultraviolet Sensitivity of Phthalic Acid Esters
with Environmental Friendliness after Modification
through Pharmacophore Modeling Associated
with the Solvation Effect
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1
MOE Key Laboratory of Resources and Environmental System Optimization,
North China Electric Power University, Beijing 102206, P. R. China
2
Department of Environmental Engineering, North China Institute of Science and Technology,
Beijing 101601, P.R.China
Submission date: 2019-05-17
Final revision date: 2019-07-11
Acceptance date: 2019-07-16
Online publication date: 2020-02-05
Publication date: 2020-03-31
Corresponding author
Yu Li
North China Electric Power University, Beijing, China, 102206, Beijing, China
Pol. J. Environ. Stud. 2020;29(3):2303-2316
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ABSTRACT
We established three-dimensional quantitative structure-activity relationship (3D QSAR)
pharmacophore models of ultraviolet (UV) absorption intensities for phthalic acid esters (PAEs).
Substituent positions were obtained using the optimum pharmacophore model, and hydrophobic
groups were used to generate PAE derivatives from the priority pollutants. The UV spectra of the PAE
derivatives were calculated using the same method, and were used to screen for PAE derivatives with
greatly enhanced UV absorption intensities. The derivatization and solvation effects on identification of
PAEs and derivatives were considered. The results showed that the Hypo1 pharmacophore model had
good predictive abilities and there were 14 PAE derivatives generated. The maximum UV absorption
intensities of three PAE derivatives were 121.85%, 105.20%, and 191.11% respectively, higher than those
of the corresponding original PAEs. Analysis of the solvation effect showed that the UV peaks red
shifted, and the degree of red shift increased with increasing solvent polarity. The minimum differential
wave numbers of the UV peaks after PAE derivatization and solvation were higher than the minimum
resolution of the UV spectrometer (0.1 nm). A two-dimensional QSAR analysis of the enhancement
mechanism can reveal the derivatization and solvation enhancement. The logKow values of DNOP
derivatives were predicted to lower by 25.55%-34.12%.