Interactions between 2-Aminobenzothiazole and natural organic matter as evidenced by CPMAS Nitrogen-15 NMR spectroscopy

Vadose Zone Journal

Volumn 8, Issue 3, 2009, Pages 670-676

  Berns, A E ^a   Conte, P ^b   Philipp, H ^a   Witte, E G ^a   Lewandowski, H ^a  

^a FORSCHUNGSZENTRUM JÜLICH   (Germany)

^b UNIVERSITY OF PALERMO   (Italy)

Author keywords

ABT, 2 aminobenzothiazole; CPMAS, cross polarization magic angle spinning; HA, humic acid; HPLC, high performance liquid chromatography; NMR, nuclear magnetic resonance

Indexed keywords

CHEMICAL BONDING; ENZYME ACTIVITY; FUNCTIONAL GROUP; HUMIC ACID; LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; ORGANIC MATTER;

EID: 70349316319     PISSN: None     EISSN: 15391663     Source Type: Journal    
DOI: 10.2136/vzj2008.0026     Document Type: Article

References (37)

1. 15N-depleted artificial compost in bound residue studies. Chemosphere 59:649-658.
2. 15N-CPMAS spectra of simazine and its metabolites: Measurements and quantum chemical calculations. Eur. J. Soil Sci. 58:882-888.
3. 15N-sulfapyridine to a model humic constituent. Environ. Sci. Technol. 41:3593-3600.
4. Bialk, H.M., and J.A. Pedersen. 2008. NMR investigation of enzymatic coupling of sulfonamide antimicrobials with humic substances. Environ. Sci. Technol. 42:106-112.
5. Bradford, M.M. 1976. Rapid and sensitive method for quantitation of microgram quantities of protein utilizing principle of protein-dye binding. Anal. Biochem. 72:248-254.
6. Brown, D.E. 1995. Fully automated baseline correction of 1D and 2D NMR-spectra using Bernstein polynomials. J. Magn. Reson. Ser. A 114:268-270.
7. 15N NMR spectroscopy: 2. Systematic investigation of whole soil and different humic fractions. Environ. Sci. Technol. 34:1549-1556.
8. Chefetz, B., Y. Chen, and Y. Hadar. 1998. Purification and characterization of laccase from Chaetomium thermophilium and its role in humification. Appl. Environ. Microbiol. 64:3175-3179.
9. Cheung, W.H., Y.S. Szeto, and G. McKay. 2007. Intraparticle diffusion processes during acid dye adsorption onto chitosan. Bioresour. Technol. 98:2897-2904.
10. Choy, K.K.H., J.F. Porter, and G. McKay. 2004. Intraparticle diffusion in single and multicomponent acid dye adsorption from wastewater onto carbon. Chem. Eng. J. 103:133-145.
11. 13C-NMR spectroscopy applied to natural organic matter. Prog. Nucl. Magn. Reson. Spectrosc. 44:215-223.
12. De Wever, H., P. Besse, and H. Verachtert. 2001. Microbial transformations of 2-substituted benzothiazoles. Appl. Microbiol. Biotechnol. 57:620-625.
13. Duer, M.J. (ed.). 2002. Solid-state NMR spectroscopy: Principles and applications. Blackwell Science Ltd., Oxford, UK.
14. Humphreys, M., N. Hall, D.A.S. Phillips, and J.A. Taylor. 2003. Synthesis and application of disperse dyes based on 1,4-bis(benzothiazol-2-yl)benzene to polyethylene terephthalate. Dyes Pigments 59:193-200.
15. Hunter, R.F. 1926. Aminobenzthiazoles: III. The tautomerism and unsaturation of the aminothiazole system. J. Chem. Soc.1385-1401.
16. 13C CP/MAS NMR of dialkyldithiocarbamate compounds with Ni(II) and Zn(II). Top. Curr. Chem. 246:271-337.
17. Jai-Nhuknan, J., A.G. Karipides, J.M. Hughes, and J.S. Cantrell. 1997. A2-amino-6-fluorobenzothiazole. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 53:381-383.
18. Joshi, S.R., P.K. Srivasta, and S.N. Tandon. 1973. Substituent effects on pK values of some thiazoles and benzothiazoles. Indian J. Chem. 11:248-249.
19. 14C)metamitron residues by sugar beets. J. Environ. Sci. Health Part B 22:509-535.
20. Knicker, H., C. Achtnich, and H. Lenke. 2001. Solid-state nitrogen-15 nuclear magnetic resonance analysis of biologically reduced 2,4,6-trinitrotoluene in a soil slurry remediation. J. Environ. Qual. 30:403-410.
21. Koglin, E., R.J. Meier, and H. Vereecken. 2006. Molecular characterisation of the bonding of herbicide metabolites to humic acid. J. Mol. Struct.: THEOCHEM 759:133-136.
22. Lynch, D.E., G. Smith, K.A. Byriel, and C.H.L. Kennard. 1998. Molecular co-crystals of carboxylic acids: XXXII. The crystal structures of the adducts of 2-aminobenzothiazole with 3,5-dinitrobenzoic acid (adduct hydrate) and 3-aminobenzoic acid, and 2-amino-2-thiazoline with 2-aminobenzoic acid. Aust. J. Chem. 51:587-592.
23. Martin, G.J., M.L. Martin, and J.-P. Gouesnard. 1981. 15N-NMR Spectroscopy. NMR Basic Principles Prog. 18. Springer-Verlag, Berlin.
24. Vara Prasad, J.V.N., A. Panapoulous, and J.R. Rubin. 2000. Thiocyanation of alkylanilines: A simple and efficient synthesis of thiosulfonates containing 2-aminobenzothiazole. Tetrahedron Lett. 41:4065-4068.
25. Rouchaud, J., P. Roucourt, M. Van Himme, F. Benoit, N. Ceustermans, J. Gillet, W. Plumier, and G. Vulsteke. 1988. Metabolism of methabenzthiazuron in the soil of pea crops. J. Agric. Food Chem. 36:642-645.
26. Schlüpen, J., F.-H. Haegel, J. Kuhlmann, H. Geisler, and M.J. Schwuger. 1999. Sorption hysteresis of pyrene on zeolite. Colloids Surf. A: Physicochem. Eng. Aspects 156:335-347.
27. Schwuger, M.J. 1970. Adsorptionskinetik von Tensiden und organischen Säuren an Aktivkohle. Chem. Ing. Tech. 42:433-438.
28. Swift, R.S. 1996. Organic matter characterization. p. 1011-1069. In D.L. Sparks (ed.) Methods of soil analysis. Part 3. Chemical methods. SSSA Book Ser. 5. SSSA, Madison, WI.
29. 15N NMR investigation of the covalent binding of reduced TNT amines to soil humic acid, model compounds, and lignocellulose. Environ. Sci. Technol. 36:3787-3796.
30. 15N NMR studies of nucleophilic addition reactions. Environ. Sci. Technol. 30:2764-2775.
31. Towns, A.D. 1999. Developments in azo disperse dyes derived from heterocyclic diazo components. Dyes Pigments 42:3-28.
32. Unold, M., R. Kasteel, J. Groeneweg, and H. Vereecken. 2009. Transport and transformation of sulfadiazine in soil columns packed with a silty loam and a loamy sand. J. Contam. Hydrol. 103:38-47.
33. Vereecken, H., U. Döring, H. Hardelauf, U. Jaekel, U. Hashagen, O. Neuendorf, H. Schwarze, and R. Seidemann. 2000. Analysis of solute transport in a heterogeneous aquifer: The Krauthausen field experiment. J. Contam.Hydrol. 45:329-358.
34. Vermeulen, T. 1953. Theory for irreversible and constant-pattern solid diffusion. Ind. Eng. Chem. 45:1664-1670.
35. Witte, E.G., H. Philipp, H.J. Schenk, and K. Schwochau. 1995. Interaction between metabolites of the urea herbicide methabenzthiazuron and humic acids. p. 624-626. In J.O. Grimalt and C. Dorronsoro (ed.) Organic geochemistry: Developments and applications to energy, climate, environment and human history. A.I.G.O.A. Donostia, San Sebastian, Spain.
36. 13C NMR spectroscopy. Org. Geochem. 29:1829-1835.
37. 13C NMR spectroscopy. Org. Geochem. 33:1727-1735.