Skip to main content

2D and 3D-QSBR Study on Biodegradation of Phenol Derivatives

Abstract

Eighteen phenol derivatives were optimized with density function theory (DFT) and comparative molecular similarity indices analysis (CoMSIA) respectively. Corresponding 2D and 3D descriptors were obtained to establish QSBR models. The biodegradation of them is mainly related to α and S ө according to the 2D QSBR, and influenced by the hydrophobicity and hydrogen bonding properties following the 3D QSBR. The 2D model performs better in stability and predictive ability than the 3D one. To some degrees, the two models verify and supplement each other. They can be used in predicting biodegradation of chlorinated, amine, nitro, nitroso and methyl phenol.

This is a preview of subscription content, access via your institution.

Fig. 1
Fig. 2
Fig. 3

References

  1. Chen YS, Chen LX, Yang J, Zhuang YY, Dai SG (1997) A study on biodegradability of 32 aromatic compounds. Environ Chem 16:43–48

    Google Scholar 

  2. Chen YJ, Wang ZY, Mao L, Gao SX (2010) QSBR study on the biodegradation rate constant of chloro-phenol compounds. Chin J Struct Chem 29:895–899

    CAS  Google Scholar 

  3. Cui SH, Liu SS, Yang J, Wang XD, Wang LS (2006) Quantitative structure-activity relationship of estrogen activities of bisphenol A analogs. Sci China Phys Mech 51:287–292

    CAS  Google Scholar 

  4. Goi A, Trapido M, Tuhkanen T (2004) A study of toxicity, biodegradability, and some by-products of ozonised nitrophenols. Adv Environ Res 8:303–311

    Article  CAS  Google Scholar 

  5. Gramatica P (2007) Principles of QSAR models validation: internal and external. QSAR Comb Sci 26:694–701

    Article  CAS  Google Scholar 

  6. Hao RX, Li JB, Zhou YW, Cheng SY, Yi Z (2009) Structure–biodegradability relationship of nonylphenol isomers during biological wastewater treatment process. Chemosphere 75:987–994

    Article  CAS  Google Scholar 

  7. Hsu YC, Yang HC, Chen JH (2005) The effects of preozonation on the biodegradability of mixed phenolic solution using a new gas-inducing reactor. Chemosphere 59:1279–1287

    Article  CAS  Google Scholar 

  8. Jiang J, Chen JN, Yu HX, Zhang F, Zhang JF, Wang LS (2004) Quantitative structure activity relationship and toxicity mechanisms of chlorophenols on cells in vitro. Chin Sci Bull 49:562–566

    Article  CAS  Google Scholar 

  9. Liu Y, Liu SS, Cui SH, Cai SX (2003) A novel quantitative structure-biodegradability relationship (QSBR) of substituted benzenes based on MHDV descriptor. J Chin Chem Soc 50:319–324

    CAS  Google Scholar 

  10. Mao L, Gao SX (2008) Reactions of estrogenic phenolic chemicals mediated by horseradish peroxidase: quantitative structure-activity relationships. Acta Sci Circumst 28:2562–2567

    CAS  Google Scholar 

  11. Pagga U (1997) Testing biodegradability with standardized methods. Chemosphere 35:2953–2972

    Article  CAS  Google Scholar 

  12. Puzyn T, Suzuki N, Haranczyk M (2008) How do the partitioning properties of polyhalogenated POPs change when chlorine is replaced with bromine? Environ Sci Technol 42:5189–5195

    Article  CAS  Google Scholar 

  13. Shi JQ, Liu HX, Sun L, Hou HF, Xu Y, Wang ZY (2011) Theoretical study on hydrophilicity and thermodynamic properties of polyfluorinated dibenzofurans. Chemosphere 84:296–304

    Article  CAS  Google Scholar 

  14. Suarez-Ojeda ME, Fabregat A, Stuber F, Fortuny A, Carrera J, Font J (2007) Catalytic wet air oxidation of substituted phenols: temperature and pressure effect on the pollutant removal, the catalyst preservation and the biodegradability enhancement. Chem Eng J 132:105–115

    Article  CAS  Google Scholar 

  15. Suarez-Ojeda ME, Carrera J, Metcalfe IS, Font J (2008) Wet air oxidation (WAO) as a precursor to biological treatment of substituted phenols: refractory nature of the WAO intermediates. Chem Eng J 144:205–212

    Article  CAS  Google Scholar 

  16. Tabak HH, Rakesh G (1993) Prediction of biodegradation kinetics using a nonlinear group contribution method. Environ Toxicol Chem 12:251–260

    Article  CAS  Google Scholar 

  17. Yang X, Liu HX, Hou HF, Flamm A, Zhang XS, Wang ZY (2010) Studies of thermodynamic properties and relative stability of a series of polyfluorinated dibenzo-p-dioxins by density functional theory. J Hazard Mater 181:969–974

    Article  CAS  Google Scholar 

  18. Zhang SX, Golbraikh A, Tropsha A (2006) The development of quantitative structure-binding affinity relationship (QSBR) models based on novel geometrical chemical descriptors of the protein-ligand interfaces. J Med Chem 49:2713–2724

    Article  CAS  Google Scholar 

Download references

Author information

Affiliations

Authors

Corresponding author

Correspondence to Fuyang Wang.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Wang, F., Shi, J. 2D and 3D-QSBR Study on Biodegradation of Phenol Derivatives. Bull Environ Contam Toxicol 89, 316–321 (2012). https://doi.org/10.1007/s00128-012-0696-6

Download citation

Keywords

  • Quantitative structure—biodegradation relationship (QSBR)
  • Phenol derivative
  • Production of carbon dioxide (PCD)
  • Density function theory (DFT)
  • Comparative molecular similarity indices analysis (CoMSIA)