Version 1.4 of the Abiotic Reduction Reaction Library contains eight reaction schemes:

· Aromatic Azo Reduction

· Sulfoxide Reduction

· N-Nitrosamine Reduction

· Quinone Reduction

· Isoxazole Cleavage

Hydrogenolysis

SCHEME:

EXAMPLES:

· Carbon tetrachloride (Elsner et al., 2004)

· Tetrachloroethene (Butler and Hayes, 1999)

· Dichlorodiphenyltrichloroethane (DDT) (Macalady et al., 1986; Larson and Weber, 1994)

· Tribromomethane (Perlinger et al., 1998)

REFERENCES:

Elsner, M. et al. Mechanisms and Products of Surface-Mediated Reductive Dehalogenation of Carbon Tetrachloride by Fe(II) on Goethite. Environ. Sci. Technol. 2004, 38, 2058-2066.

Butler, E.C.; Hayes, K.F. Kinetics of the Transformation of Trichloroethylene and Tetrachloroethylene by Iron Sulfide. Environ. Sci. Technol. 1999, 33, 2021-2027.

Macalady, D.L.; Tratnyek, P.G.; Grundl, T.J. Review Paper: Abiotic Reduction Reactions of Anthropogenic Organic Chemicals in Anaerobic Systems: A Critical Review. J. Contam. Hydrol. 1986, 1, 1-28.

Larson, R.A. and E.J. Weber. Reaction Mechanisms in Environmental Organic Chemistry. Boca Raton: CRC Press, Inc., 1994.

Perlinger, J.A.; Buschmann, J.; Angst, W.; Schwarzenbach, R.P. Iron Porphyrin and Mercaptojuglone Mediated Reduction of Polyhalogenated Methanes and Ethanes in Homogeneous Aqueous Solution. Environ. Sci. Technol. 1998, 32, 2431-2437.

Vicinal Dehalogenation

SCHEME:

EXAMPLES:

· Hexachloroethane (Perlinger et al., 1996)

· 1,1,1,2-tetrachloro-2,2-bis(p-chlorophenyl)ethane (Alpha-chloro-DDT, DTE) (Macalady et al., 1986; Larson and Weber, 1994)

· Tetrachloroethane (Butler and Hayes, 2000)

REFERENCES:

Perlinger, J.A.; Angst, W.; Schwarzenbach, R.P. Kinetics of the Reduction of Hexachloroethane by Juglone in Solutions Containing Hydrogen Sulfide. Environ. Sci. Technol. 1996, 30, 3408-3417.

Larson, R.A. and E.J. Weber. Reaction Mechanisms in Environmental Organic Chemistry. Boca Raton: CRC Press, Inc., 1994.

Butler, E.C.; Hayes, K.F. Kinetics of the Transformation of Halogenated Aliphatic Compounds by Iron Sulfide. Environ. Sci. Technol. 2000, 34, 422-429.

Nitroaromatic Reduction

SCHEME:

EXAMPLES:

· P-Chloronitrobenzene (Klausen et al., 1995)

· 3-Bromo-5-nitrobenzene-1,2-diamine (Weber and Adams, 1995; Larson and Weber, 1994)

· 1,2,4,5-Tetrachloro-3-nitrobenzene (Macalady et al., 1986)

· O,O-diethyl O-4-nitrophenyl Phosphorothioate (Parathion) (Macalady et al., 1986)

REFERENCES:

Klausen, J.; Trober, S.P.; Haderlein, S.B.; Schwarzenbach, R.P. Reduction of Substituted Nitrobenzenes by Fe(II) in Aqueous Mineral Suspensions. Environ. Sci. Technol. 1995, 29, 2396-2404.

Weber, E.J.; Adams, R.L. Chemical- and Sediment-Mediated Reduction of the Azo Dye Disperse Blue 79. Environ. Sci. Technol. 1995, 29, 1163-1170.

Larson, R.A. and E.J. Weber. Reaction Mechanisms in Environmental Organic Chemistry. Boca Raton: CRC Press, Inc., 1994.

Aromatic Azo Reduction

SCHEME:

EXAMPLES:

· 5-amino-2-{2-[4-(dimethylamino)phenyl]diazen-1-yl}benzoic acid (Weber and Wolfe, 1987)

· Disperse Blue 79 (Weber and Adams, 1995; Larson and Weber, 1994)

· 1-({4-[(E)-2-phenyldiazen-1-yl]phenyl}amino)propan-2-ol (Substituted 4-Aminoazobenzene) (Weber, 1996)

· 4-[(E)-2-{4-[(2-hydroxypropyl)amino]phenyl}diazen-1-yl]benzonitrile (Substituted 4-cyano-4’-aminoazobenzene) (Zhang and Weber, 2009)

REFERENCES:

Weber, E.J.; Wolfe, N.L. Kinetic Studies of the Reduction of Aromatic Azo Compounds in Anaerobic Sediment/Water Systems. Environ. Toxicol. Chem. 1987, 6, 911-919.

Weber, E.J.; Adams, R.L. Chemical- and Sediment-Mediated Reduction of the Azo Dye Disperse Blue 79. Environ. Sci. Technol. 1995, 29, 1163-1170.

Larson, R.A. and E.J. Weber. Reaction Mechanisms in Environmental Organic Chemistry. Boca Raton: CRC Press, Inc., 1994.

Weber, E.J. Iron-Mediated Reductive Transformations: Investigation of Reaction Mechanism. Environ. Sci. Technol. 1996, 30, 716-719.

Zhang, H.; Weber, E.J. Elucidating the Role of Electron Shuttles in Reductive Transformations in Anaerobic Sediments. Environ. Sci. Technol. 2009, 43, 1042-1048.

Sulfoxide Reduction

SCHEME:

EXAMPLES:

· Phorate Sulfoxide (Larson and Weber, 1994)

· Aldicarb Sulfoxide (Larson and Weber, 1994)

REFERENCES:

Larson, R.A. and E.J. Weber. Reaction Mechanisms in Environmental Organic Chemistry. Boca Raton: CRC Press, Inc., 1994.

N-Nitrosoamine Reduction

SCHEME:

EXAMPLES:

· Nitrosodiphenylamine (Larson and Weber, 1994)

· N-Nitrosoatrazine (Larson and Weber, 1994)

· Nitrosodimethylamine (Kulikova et al., 2009)

REFERENCES:

Larson, R.A. and E.J. Weber. Reaction Mechanisms in Environmental Organic Chemistry. Boca Raton: CRC Press, Inc., 1994.

Kulikova, N.; Baker, M.; Gabryelski, W. Collision induced dissociation of protonated N-nitrosodimethylamine by ion trap mass spectrometry: Ultimate carcinogens in gas phase. Int. J. Mass Spec. 2009, 288, 75-83.

Quinone Reduction

SCHEME:

EXAMPLES:

· Anilinohydroquinone (Colon et al., 2002)

· 2,6-dichlorophenolindophenol (Tonomura et al., 1978; Larson and Weber, 1994)

· Tetramethoxycyclohexa-2,5-diene-1,4-dione (Ref ??)

REFERENCES:

Colón, D.; Weber, E.J.; Baughman, G.L. Sediment-Associated Reactions of Aromatic Amines. 2. QSAR Development. Environ. Sci. Technol. 2002, 36, 2443-2450.

Tonomura, B.; Nakatani, H.; Ohnishi, M.; Yamaguchi-Ito, J.; Hiromi, K. Reduction for 2,6-Dichlorophenolindophenol and Potassium Ferricyanide by L-Ascorbic Acid. Anal. Biochem. 1978, 84, 370-383.

Larson, R.A. and E.J. Weber. Reaction Mechanisms in Environmental Organic Chemistry. Boca Raton: CRC Press, Inc., 1994.

Isoxazole Cleavage

SCHEME:

EXAMPLES:

· Sulfamethoxazole (Mohatt et al., 2011)

REFERENCES:

Mohatt, J.L.; Hu, L.; Finneran, K.T.; Strathmann, T.J. Microbially Mediated Abiotic Transformation of the Antimicrobial Agent Sulfamethoxazole under Iron-Reducing Soil Conditions. Environ. Sci. Technol. 2011, 45, 4793-4801.