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4 protocols using 4 nitroaniline

1

Synthesis and Characterization of Aromatic Compounds

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Nitrobenzene (+99%), 1,4-diNitrobenzene (+98%), 4-chloroaniline (+98%) and naphthalene (+99%) were purchased from Acros Organics Co.; 3-Nitroaniline (+98%) was purchased from Sigma-Aldrich Chemistry Co.; 2-Chlorophenol (+99%), 4-chlorophenol (+99%), 2-chloroaniline (+98%), 2-nitroaniline (+99%) and 4-methylaniline (+99.7%) were purchased from Aladdin Reagent Co.; 4-MethylNitrobenzene (+99.5%), 4-chlosroNitrobenzene (+98%), phenanthrene (+98%) and pyrene (+97%) were purchased from Fluka Chemistry Co.; 1,2-DiNitrobenzene (+98%), 1,3-dinitro benzene (+99%) and 1,3,5-triNitrobenzene (wetted with 40% water) were purchased from Tokyo Chemical Industry Co.; 2,4-Dichlorophenol (+99.5%), 4-methylphenol (+98%), 2-nitrophenol (+99%), 3-nitrophenol (+99%), 4-nitrophenol (+99.5%) and 4-nitroaniline (+99.5%) were purchased from Sinopharm Chemical Reagent Co.; Aniline (+99.5%) was purchased from Shanghai Reagent Co.; and phenol (+99.7%) was purchased from Hangzhou Shuanglin Chemical Co. All these aromatic chemicals were used as received. The selected properties including water solubility (Sw), octanol-water partitioning coefficients (logKow), molecular weight, maximum absorption wavelength (λmax), dissociated constant (pKa) of the 25 investigated aromatic chemicals are listed in Table S3.
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2

Synthesis of Organic Compounds

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Imidazole, 1‐methylImidazole, sodium hydroxide, toluene, dimethyl sulfoxide, dibromomethane, nitric acid, sulfuric acid, trifluoromethanesulfonic acid, phosphoric acid, 4‐Nitroaniline, acetone and methanol were AC grade purchased from Sinopharm Chemical Reagent Co., Ltd. Pentaerythrityl tetrabromide were AC grade purchased from Alfa Aesar.
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3

Physicochemical Properties of Organic Compounds

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4-Nitrophenol (4-NP, +99.5 %), nitrobenzene (NB, +99 %), 3-nitrophenol (3-NP, +99.7 %), and 1,4-dinitrobenzene (4-DNB, +98 %) were obtained from Aladdin Reagent Co. (Shanghai, China). 4-Chloronitrobenzene (4-NCB, +98 %) was purchased from Fluka Chemistry Co. (Seelze, Germany). 4-Nitroaniline (4-NA, +99.5 %) was purchased from Sinopharm Chemical Reagent Co. (Beijing, China). Their physicochemical properties are displayed in Table 1.

Physicochemical properties of selected organic compounds.

Table 1
CompoundsAbbrMWSWλmaxpKaVI/100π*βmαmσlogKow
4-nitrophenol4-NP139.11160003177.150.6851.010.320.930.6031.79
nitrobenzeneNB123.111936269/0.6311.010.3000.5631.85
4-Nitroaniline4-NA138.136003801.000.6850.910.460.470.6111.39
3-nitrophenol3-NP139.11140002738.280.6851.060.330.820.6912
1,4-dinitrobenzene4-DNB168.1169266/0.7331.310.4600.6481.48
4-chloronitrobenzene4-NCB157.56225279/0.7211.110.2600.6432.39

Abbr: abbreviation for the compound; MW: molecular weight (g/mol); SW: water solubility (mg/L); λmax: maximum absorption wavelength (nm); pKa: dissociated constant; VI/100: intrinsic molar volume (mg/mol); π*: polarity/polarizability parameter; βm: hydrogen-bonding acceptor parameter; αm: hydrogen-bonding donor parameter; σ: the maximum cross-sectional area (nm2); Kow: octanol/water partition coefficient. Data obtained from Ref. [31 (link)].

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4

Nitro-Compound Reduction Protocols

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Hydrogen peroxide (H2O2), nitrobenzene, 4-nitroanisole, 4-nitrotoluene, 4-nitroaniline, 4-chloronitrobenzene, 4-bromonitrobenzene, 4-nitrobenzoic acid, 4-nitrobenzonitrile, 3-bromonitrobenzene, 3-chloronitrobenzene, 3-nitrobenzoic acid, 4-nitrostyrene, 4-nitrophenol (4-NP), thiourea, urea, and sodium borohydride (NaBH4) were purchased from Sinopharm Chemical Reagent Co, Ltd. (Shanghai, China). Potassium tetrachloropalladate (K2PdCl4) was procured from Aladdin Chemistry Co., Ltd. (Shanghai, China). The rest of the chemicals were obtained from Sigma-Aldrich. Deionized water was used for all synthesis and experiments.
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