Issue

Vol. 32 No. 5 (2020): Vol 32 Issue 5

Copyright (c) 2020 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

N-t-Butyl-α-aryl Nitrones as Potent Spin Traps: DFT Analysis of Electron Localization Function Topology, Local Selectivity, Reactivity and Solvent Effects

Nivedita Acharjee
Department of Chemistry, Durgapur Government College, J.N. Avenue, Durgapur-713214, India
https://orcid.org/0000-0001-8354-8693
Sourav Mondal
Department of Chemistry, Durgapur Government College, J.N. Avenue, Durgapur-713214, India

Corresponding Author(s) : Nivedita Acharjee

nivchem@gmail.com

Asian Journal of Chemistry, Vol. 32 No. 5 (2020): Vol 32 Issue 5

Abstract

Density functional theory studies were performed to analyze the reactivity and selectivity of radical capture by N-t-butyl-α-aryl nitrones. Biologically relevant three important radicals viz. hydroxyl, methyl and hydroperoxyl were selected for the study. Topological analysis of the electron localization function (ELF) allows to classify these nitrones as zwitter-ionic type three atom components (TAC). Effects of electron withdrawing and electron donating C-aryl substituents on the electronic chemical potentials, global hardness, electrophilic and nucleophilic indices of nitrones were observed. Radical attack at the carbon atom was predicted by Merz-Kollman algorithm, which is in agreement with the experiments unlike the natural population analysis. Hydroxyl adducts were predicted to be more stable than methyl and hydroperoxyl adducts. cis-Adducts were more stable than the trans-, with the highest differences in stability noted for the methyl adducts. Relative energies of adducts was lowered in non-polar solvents and thus increase in stability was observed along the series from water to heptane.

Keywords

Spin trapping Conceptual DFT Nitrones Free energy Electron localization function Merz-Kollman algorithm
Acharjee, N., & Mondal, S. (2020). N-t-Butyl-α-aryl Nitrones as Potent Spin Traps: DFT Analysis of Electron Localization Function Topology, Local Selectivity, Reactivity and Solvent Effects. Asian Journal of Chemistry, 32(5), 1191–1196. Retrieved from https://asianpubs.org/index.php/ajchem/article/view/2507
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. A. Phaniendra, D.B. Jestadi, and L. Periyasamy, Indian. J. Clin. Biochem., 30, 11 (2015); https://doi.org/10.1007/s12291-014-0446-0
  2. C. C. Benz and C. Yau, Nat. Rev. Cancer., 8, 875 (2008); https://doi.org/10.1038/nrc2522
  3. L. M. Sayre, G. Perry and M. A. Smith, Chem. Res. Toxicol., 21, 172 (2008); https://doi.org/10.1021/tx700210j
  4. R. A. Cohen and X. Tong, J. Cardiovasc. Pharmacol., 55, 308 (2010); https://doi.org/10.1097/fjc.0b013e3181d89670
  5. A. Nawab, A. Nichols, R. Klug, J. I. Shapiro and K. Sodhi, J Clin Cell Immunol., 8, 505, (2017); https://doi.org/10.4172/2155-9899.1000505
  6. G.B. Gonzalez, C. Aliaga, C.O. Azar, M.C.Z.-Lopez, M. Gonzalez and H. Cerecetto, Curr. Org. Chem., 21, 2062 (2017); https://doi.org/10.2174/1385272821666170228131324
  7. R.A. Floyd, H.K. Chandru, T. He and R. Towner, Anticancer Agents Med. Chem., 11, 373 (2011); https://doi.org/10.2174/187152011795677517
  8. Y. Kotake and E.G. Janzen, J. Am. Chem. Soc., 113, 9503 (1991); https://doi.org/10.1021/ja00025a013
  9. E.G. Janzen, Y. Kotake and R.D. Hinton, Free Radical. Biol. Med., 12, 169 (1992); https://doi.org/10.1016/0891-5849(92)90011-5
  10. K. Makino, T. Hagiwara and A. Murakami, Radiat. Phys. Chem., 37, 657 (1991); https://doi.org/10.1016/1359-0197(91)90164-W
  11. S.E. Bottle and A.S. Micallef, Org. Biomol. Chem., 1, 2581 (2003); https://doi.org/10.1039/B300642E
  12. N. Vrbjar, S. Zöllner, R.F. Haseloff, M. Pissarek and I.E. Blasig, Mol. Cell. Biochem., 186, 107–115 (1998); https://doi.org/10.1023/A:1006875515357
  13. P.A. Lapchak, D.F. Chapman and J.A. Zivin, Stroke, 32, 147 (2001); https://doi.org/10.1161/01.STR.32.1.147
  14. D.N. Polovyanenko, V.F. Plyusnin, V.A. Reznikov, V.V. Khramtsov and E.G. Bagryanskaya, J. Phys. Chem. B., 112, 4841 (2008); https://doi.org/10.1021/jp711548x
  15. V. Marchand, N. Charlier, J. Verrax, P. BucCalderon, P. Levêque and B. Gallez, PLoS ONE., 12, e0172998 (2017)’ https://doi.org/10.1371/journal.pone.0172998
  16. P. D. Sawant, Cosmetics., 5, 8 (2018); https://doi.org/10.3390/cosmetics5010008
  17. F.A. Villamena, C.M. Hadad and J.L. Zweier, J. Am. Chem. Soc., 126, 1816 (2004); https://doi.org/10.1021/ja038838k
  18. F.A. Villamena, C.M. Hadad, and J.L. Zweier., J. Phys. Chem. A., 109, 1662 (2005); https://doi.org/10.1021/jp0451492
  19. S.-U. Kim and F.A. Villamena, J. Phys. Chem. A., 116, 886 (2012); https://doi.org/10.1021/jp209896n
  20. A.D. Becke and K.E. Edgecombe, J. Chem. Phys., 92, 5397 (1990); https://doi.org/10.1063/1.458517
  21. B. Silvi and A. Savin, Nature., 371, 683 (1994); https://www.nature.com/articles/371683a0
  22. L.R. Domingo, M. Ríos-Gutiérrez and P. Pérez, Molecules., 21, 748 (2016); https://doi.org/10.3390/molecules21060748
  23. A.D. Becke, Phys. Rev. A., 38, 3098 (1988); https://doi.org/10.1103/PhysRevA.38.3098
  24. C. Lee, W. Yang and R.G. Parr, Phys. Rev. B.,37, 785 (1988); https://doi.org/10.1103/PhysRevB.37.785
  25. H.B. Schlegel, J. Comput. Chem., 3, 214 (1982); https://doi.org/10.1002/jcc.540030212
  26. H.B. Schlegel, ed.: D.R. Yarkony, Modern Electronic Structure Theory, World Scientific Publishing: Singapore (1994).
  27. J. Tomasi and M. Persico, Chem. Rev., 94, 2027 (1994); https://doi.org/10.1021/cr00031a013
  28. E. Cancés, B. Mennucci and J. Tomasi, Chem. Phys., 107, 3032 (1997); https://doi.org/10.1063/1.474659
  29. V. Barone, M. Cossi and J. Tomasi, J. Comput. Chem., 19, 404 (1998); https://doi.org/10.1002/(SICI)1096-987X(199803)19:4<404::AIDJCC3>3.0.CO;2-W
  30. T. Lu and F. Chen, J. Comput. Chem., 33, 580 (2012); https://doi.org/10.1002/jcc.22885
  31. W. Humphrey, A. Dalke and K. Schulten, J. Molec. Graphics.,14, 33 (1996); https://doi.org/10.1016/0263-7855(96)00018-5
  32. E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng and T.E. Ferrin, J. Comput. Chem., 25, 1605 (2004); https://doi.org/10.1002/jcc.20084
  33. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski and D.J. Fox, Gaussian Inc., Wallingford CT, Gaussian 09, Revision D.01 (2009).
  34. L.R. Domingo, Molecules, 21, 1319 (2016); https://doi.org/10.3390/molecules21101319
  35. M.R. Gutierrez and L.R. Domingo, Eur. J. Org. Chem., 2, 267 (2019); https://doi.org/10.1002/ejoc.201800916
  36. L.R. Domingo, M.J. Aurell, P. Perez and R. Contreras, Tetrahedron, 58, 4417 (2002); https://doi.org/10.1016/S0040-4020(02)00410-6
  37. L.R. Domingo, E. Chamorro and P. Pérez, J. Org. Chem., 73, 4615 (2008); https://doi.org/10.1021/jo800572a
  38. A.E. Reed, R.B. Weinstock and F. Weinhold, J. Chem. Phys., 83, 735 (1985); https://doi.org/10.1063/1.449486
  39. B.H. Besler, K.M. Jr. Merz and P.A. Kollman, J. Comput. Chem., 11, 431 (1990); https://doi.org/10.1002/jcc.540110404
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 2 Download : 1