Yan-dan Li; Bing-bing Li; Dan Zhang; Hong-han Chen; Hai-jiao Xie; Er-ping Bi

doi:10.26599/JGSE.2026.9280090

doi: 10.26599/JGSE.2026.9280090

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出版历程
- 收稿日期: 2025-08-31
- 录用日期: 2026-03-16
- 网络出版日期: 2026-10-10
- 刊出日期: 2026-12-15

Adsorption mechanism of flumequine onto kaolinite: Evidence from density functional theory calculations and the effects of Cu(II)

Yan-dan Li^{1, 2, T},
Bing-bing Li^{1, T},
Dan Zhang²,
Hong-han Chen¹,
Hai-jiao Xie³,
Er-ping Bi^{1
, ,}

1.
School of Water Resources and Environment, Key Laboratory of Groundwater Conservation of MWR, and State Key Laboratory of Geomicrobiology and Environmental Changes, China University of Geosciences (Beijing), Beijing 100083, China
2.
Beijing Key Laboratory for Risk Modeling and Remediation of Contaminated Sites, Beijing Municipal Research Institute of Eco-Environmental Protection, Beijing 100037, China
3.
Hangzhou Yanqu Information Technology Co., Ltd, Hangzhou 310003, China

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Corresponding author: bi@cugb.edu.cn

These authors contributed equally to this work.

摘要

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Abstract: Flumequine (FLU) is widely applied in animal husbandry and can enter sediment and groundwater systems. However, the adsorption mechanisms of FLU onto clay minerals remain unclear. Density Functional Theory (DFT) calculations were employed to elucidate the adsorption mechanism of FLU onto kaolinite, and batch adsorption experiments were conducted to investigate the adsorption behavior of FLU. Results of DFT calculations demonstrated that the carboxyl group of FLU interacted with the hydroxyl groups on the kaolinite (001) surface via hydrogen bonding and electrostatic interactions, which were the main adsorption mechanisms. The adsorption of FLU onto kaolinite exhibited pH dependence, due to pH-induced variations in both the speciation of FLU and the surface charge of kaolinite. Ionic strength negatively affected FLU adsorption because NaCl could decrease the activity of FLU, and Cl⁻ could also compete for the adsorption sites with FLU⁻. With the addition of Cu(II), the species Cu(FLU⁻)⁺ was formed, and it had stronger adsorption affinity for kaolinite than FLU. However, Cu²⁺ could compete for adsorption sites with Cu(FLU⁻)⁺. Therefore, the molar concentration difference between Cu(FLU⁻)⁺ and Cu²⁺ played a crucial role in FLU adsorption. When the ratio of this difference in the binary systems to the adsorbed FLU in the single system exceeded 1.0, Cu(II) addition significantly enhanced FLU adsorption onto kaolinite; otherwise, it inhibited adsorption. Our findings indicate that hydrogeochemical conditions and coexisting heavy metal ions should be considered when studying the environmental fate of quinolone antibiotics.
- Flumequine /
- Kaolinite /
- Adsorption mechanism /
- Density functional theory /
- pH and ionic strength /
- Coexisting Cu(II)
These authors contributed equally to this work.
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Figure 1. The adsorption kinetics of FLU and Cu(II) onto kaolinite (final solution pH 5.4 ± 0.1) (a) FLU (0.065 mM) with/without 0.05 and 0.20 mM Cu(II); (b) Cu(II) (initial concentration 0.20 mM) with/without 0.065 mM FLU

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Figure 2. Adsorption isotherm fitting curves of FLU with/without 0.10 mM Cu(II) under different final pH conditions ((a) pH 5.4 ± 0.1; (b) pH 7.8 ± 0.1)

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Figure 3. The adsorption amount of FLU onto kaolinite with different NaCl concentrations

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Figure 4. Three optimized configurations of FLU adsorption onto kaolinite (001) surface

Notes: (a): KAO-CO; (b): KAO-COOH; (c): KAO-F

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Figure 5. The charge density difference diagrams of three adsorption configurations

Notes: (a): KAO-CO; (b): KAO-COOH; (c): KAO-F

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Figure 6. Solution species of 0.07 mM FLU with (a) 0.05 mM Cu(II); (b) 0.10 mM Cu(II) and (c) 0.20 mM Cu(II) at different pH values calculated by the software ChemEQL.

Notes: The stability constants were obtained from reference (Urbaniak and Kokot, 2009): Cu²⁺+ FLU⁻$\Leftrightarrow $Cu(FLU⁻)⁺, logβ = 6.00; Cu²⁺+2 FLU⁻$\Leftrightarrow $Cu(FLU⁻)₂⁰, logβ = 11.00; FLU⁻+H⁺$\Leftrightarrow $FLU⁰, pK_a = 6.35

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Figure 7. (a) Adsorption of FLU (0.07 mM) with/without 0.05, 0.10, and 0.20 mM Cu(II) as a function of pH (25 °C, equilibration time 48 h, background electrolyte 0.01 M NaCl); (b) the molar concentration ratios of the difference between Cu(FLU⁻)⁺ and Cu²⁺ in the binary systems (i.e., FLU and Cu(II)) to the adsorbed FLU in the single system (i.e., FLU only) as a function of pH

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Figure 8. Desorption of FLU in the absence/presence of Cu(II) (0.10 mM) in solution with a final pH 6.4 ± 0.1

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S1. The optimized structure of kaolinite (001) surface (a) Top view; and (b) Side view

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S2. The variation of COHP with energy for the bonds in the KAO-CO adsorption configuration (a) the H₁₁…O₃₉ bond; and (b) the H₁₄…O₃₈ bond

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S3. The variation of COHP with energy for the bonds in the KAO-COOH adsorption configuration (a) the H₁₆…O₃₈ bond; (b) the H₄…O₃₉ bond; (c) the H₆…O₃₈ bond; and (d) the O₃₄…H₂₅ bond

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S4. The variation of COHP with energy for the H₁₁…F bond in the KAO-F adsorption configuration

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Table 1. Fitting parameters of isotherm models of FLU with/without 0.10 mM Cu(II)

pH	Adsorbates	Linear		Freundlich			Langmuir
pH	Adsorbates	K_d⁽¹⁾	R²	K_F⁽²⁾	n	R²	q_m	K_L⁽³⁾	R²
5.4	FLU	105.19	0.97	23.16	0.54	0.99	7.79	27.98	0.99
5.4	FLU+Cu(II)	63.79	0.99	20.71	0.66	0.99	5.76	17.16	0.98
7.8	FLU	6.23	0.84	1.48	0.51	0.60	1.15	9.11	0.18
7.8	FLU+Cu(II)	144.66	0.99	81.69	0.84	0.98	9.35	32.17	0.95
Notes: (1) the unit is L/kg; (2) the unit is (mmol/kg)/(mM)ⁿ; and (3) the unit is L/mmol

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Table 2. The average Bader charge and the amount of charge change of each atom in the three adsorption configurations

Items	Charge			△Charge
Items	KAO-CO	KAO-COOH	KAO-F	KAO-CO	KAO-COOH	KAO-F
Al⁽¹⁾	0.511	0.512	0.511	−2.489	−2.488	−2.489
Si⁽¹⁾	0.816	0.816	0.816	−3.184	−3.184	−3.184
O⁽¹⁾	7.531	7.534	7.527	1.531	1.534	1.527
H⁽¹⁾	0.392	0.385	0.400	−0.608	−0.615	−0.600
C⁽²⁾	3.726	3.721	3.730	−0.277	−0.278	−0.270
N⁽²⁾	6.200	6.190	6.190	1.200	1.190	1.190
F⁽²⁾	7.640	7.630	7.670	0.640	0.630	0.670
O⁽²⁾	7.138	7.149	7.119	1.138	1.149	1.119
H⁽²⁾	0.879	0.883	0.880	−0.121	−0.117	−0.120
Q⁽³⁾	−	−	−	0.031	0.033	0.002
Notes: (1) the atoms of the kaolinite (001) surface; (2) the atoms of FLU; and (3) the amounts of charge transfer of the three configurations (positive Q indicated that charge was transferred from FLU to the kaolinite surface)

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S1. Main physicochemical properties of FLU

Compound	Molecular Weight (g/mol)	pK_a	Log K_ow	Structure
FLU	261.25	6.35⁽¹⁾	1.72⁽²⁾
Note: (1) (Feng et al., 2016); and (2) (Van Doorslaer et al., 2014)

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S2. Parameters of PFOM and PSOM

Adsorbates	q_e⁽¹⁾	PFOM			PSOM
Adsorbates	q_e⁽¹⁾	k₁⁽²⁾	q_e1⁽¹⁾	R²	k₂⁽³⁾	q_e2⁽¹⁾	R²
FLU	4.00	0.13	3.95	0.93	0.19	4.04	0.99
Note: (1) the unit is mmol/kg; (2) the unit is h⁻¹; and (3) the unit is kg/(mmol·h)

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S3. Bonding analysis of the three adsorption configurations

configurations	Bond	Bond Length (Å)	ICOHP (eV)
KAO-CO	KAO-H₁₁…O₃₉-CO	1.83	−0.67
KAO-CO	KAO-H₁₄…O₃₈-COOH	1.88	−0.55
KAO-COOH	KAO-H₁₆…O₃₈-COOH	1.75	−0.88
	KAO-H₄…O₃₉-CO	1.81	−0.76
	KAO-H₆…O₃₈-COOH	1.96	−0.43
	KAO-O₃₄…H₂₅-COOH	1.98	−0.66
KAO-F	KAO-H₁₁…F	2.22	−0.20

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