Abstract
The study of pollution due to combined antibiotics and metals is urgently needed. Photochemical processes are an important transformation pathway for antibiotics in the environment. The mechanisms underlying the effects of metal-ion complexation on the aquatic photochemical transformation of antibiotics in different dissociation forms are crucial problems in science, and beg solutions. Herein, we investigated the mechanisms of direct photolysis of norfloxacin (NOR) in different dissociation forms in water and metal ion Mg2+ effects using quantum chemical calculations. Results show that different dissociation forms of NOR had different maximum electronic absorbance wavelengths (NOR2+ < NOR0 < NOR+) and showed different photolysis reactivity. Analysis of transition states (TS) and reaction activation energies (Ea) indicated NOR+ generally underwent loss of the piperazine ring (C10–N13 bond cleavage) and damage to piperazine ring (N13–C14 bond cleavage). For NOR2+, the main direct photolysis pathways were de-ethylation (N7–C8 bond cleavage) and decarboxylation (C2–C5 bond cleavage). Furthermore, the presence of Mg2+ changed the order of the wavelength at maximum electronic absorbance (NOR+-Mg2+ < NOR0-Mg2+ < NOR2+-Mg2+) and increased the intensities of absorbance peaks of all three dissociation species of NOR, implying that Mg2+ played an important role in the direct photolysis of NOR0, NOR+, and NOR2+. The calculated TS results indicated that the presence of Mg2+ increased Ea for most direct photolysis pathways of NOR, while it decreased Ea for some direct photolysis pathways such as the loss of the piperazine ring and the damage of the piperazine ring of NOR0 and the defluorination of NOR+.
Highlights
Antibiotics are widely used in aquaculture, animal husbandry, and medical treatment, due to the fact that they can either kill or inhibit the growth of bacteria [1,2]
Results show that different dissociation forms of NOR had different maximum electronic absorbance wavelengths (NOR2+ < NOR0 < NOR+ ) and showed different photolysis reactivity
Antibiotics are frequently released into the environment due to negligence, and they are frequently detected in the aquatic environment [1,3]
Summary
Antibiotics are widely used in aquaculture, animal husbandry, and medical treatment, due to the fact that they can either kill or inhibit the growth of bacteria [1,2]. A lot of attention has been devoted to studies on the behavior, fate, and degradation methods of NOR in the aquatic environment [10,11,12]. Photolysis is expected to play an important role in determining the fate and behavior of fluoroquinolone antibiotics including NOR in some sunlit surface waters [13,14,15,16,17,18]. For the direct photolysis of organic pollutants, a molecule itself absorbs photons and is degraded [19]. Indirect photolysis may include reaction with transient excited species such as singlet oxygen, hydroxyl radical, triplet excited state dissolved organic matter, or other reactive
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