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000000716 0247_ $$2DOI$$a10.1016/j.chemosphere.2008.05.038
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000000716 084__ $$2WoS$$aEnvironmental Sciences
000000716 1001_ $$0P:(DE-HGF)0$$aHuschek, G.$$b0
000000716 245__ $$aRe-evaluation of the conformational structure of sulfadiazine species using NMR and ab initio DFT studies and its implication on sorption and degradation
000000716 260__ $$aAmsterdam [u.a.]$$bElsevier Science$$c2008
000000716 300__ $$a1448 - 1454
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000000716 440_0 $$01228$$aChemosphere$$v72$$x0045-6535$$y10
000000716 500__ $$aThe authors gratefully acknowledge the financial support provided by the German Research Foundation (DFG - Deutsche Forschungsgemeinschaft) for Research Unit 566 Veterinary Medicines in Soil. We would also like to thank Dr. A. Koch for his excellent technical and analytical support.
000000716 520__ $$aIn the environment, the sorption and the degradation of organic pollutants are of increasing interest. The investigation of the chemical structures provides a basis for the development of a suitable binding model approach and for the mechanistic understanding of the chemical fate processes. The aim of this study was the identification of different species of the antibiotic compound sulfadiazine (SDZ) using (1)H and (13)C NMR experiments and ab initio density functional theory (DFT) calculations. In the neutral, aprotic solvent dimethylsulfoxide-d(6) (DMSO-d(6)), a new sulfadiazine structure containing an O-H-N hydrogen bond was identified. In the protic solvent water-d(2) and in dependence on pH and the position of the amidogen hydrogen atom nine possible SDZ conformations were analyzed and five structures were identified. Good conformity between theory and calculation of (1)H NMR was observed. Unfortunately, (13)C NMR is not sensitive enough for comparison and differentiation. In order to verify the identified structures, additional NBO/NLMO (natural localized molecular orbital) analyses were conducted (calculation of net atomic charges, bond polarity, atomic valence, and electron delocalization). Finally, conformation optimizations were performed in order to investigate the stability of the SDZ species. We showed that SDZ contains no S=O double bond, but that it has two S-O single bonds. Surprisingly, negative charges were observed at the pyrimidine nitrogen atom. With these results, the known structure of SDZ was revised. Studies of the geometrical structure and the torsion angles showed that SDZ is very flexible and can be easily fitted to the sorbent. These observations would explain the strong sorbance and hence the rapid formation of non-extractable residues in the environment because SDZ acts as a strong ligand. These results show that that the sulfonamide hydrogen is important for the biological activity but the pyrimidine nitrogen and the sulfonamide oxygen is responsible for the sorbance in environment.
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000000716 650_2 $$2MeSH$$aAbsorption
000000716 650_2 $$2MeSH$$aHydrogen-Ion Concentration
000000716 650_2 $$2MeSH$$aMagnetic Resonance Spectroscopy: methods
000000716 650_2 $$2MeSH$$aModels, Molecular
000000716 650_2 $$2MeSH$$aMolecular Structure
000000716 650_2 $$2MeSH$$aSulfadiazine: chemistry
000000716 650_7 $$068-35-9$$2NLM Chemicals$$aSulfadiazine
000000716 650_7 $$2WoSType$$aJ
000000716 65320 $$2Author$$asulfadiazine
000000716 65320 $$2Author$$aNMR
000000716 65320 $$2Author$$astructure elucidation
000000716 65320 $$2Author$$aantibiotic
000000716 65320 $$2Author$$asulfonamide
000000716 7001_ $$0P:(DE-HGF)0$$aHollmann, D.$$b1
000000716 7001_ $$0P:(DE-HGF)0$$aKurowski, N.$$b2
000000716 7001_ $$0P:(DE-HGF)0$$aKaupenjohann, M.$$b3
000000716 7001_ $$0P:(DE-Juel1)129549$$aVereecken, H.$$b4$$uFZJ
000000716 773__ $$0PERI:(DE-600)1496851-4$$a10.1016/j.chemosphere.2008.05.038$$gVol. 72, p. 1448 - 1454$$p1448 - 1454$$q72<1448 - 1454$$tChemosphere$$v72$$x0045-6535$$y2008
000000716 8567_ $$uhttp://dx.doi.org/10.1016/j.chemosphere.2008.05.038
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