Browse > Article
http://dx.doi.org/10.5012/bkcs.2012.33.11.3607

DFT/B3LYP Study of the Substituent Effects on the Reaction Enthalpies of the Antioxidant Mechanisms of Magnolol Derivatives in the Gas-Phase and Water  

Najafi, Meysam (Department of physiology, Faculty of Medicine, Kermanshah University of Medical Sciences)
Najafi, Mohammad (Department of physiology, Faculty of Medicine, Kermanshah University of Medical Sciences)
Najafi, Houshang (Department of physiology, Faculty of Medicine, Kermanshah University of Medical Sciences)
Publication Information
Bulletin of the Korean Chemical Society / v.33, no.11, 2012 , pp. 3607-3617 More about this Journal
Abstract
In this paper, the study of various ortho- and meta-substituted Magnolol derivatives is presented. The reaction enthalpies related to three antioxidant action mechanisms HAT, SET-PT and SPLET for substituted Magnolols have been calculated using DFT/B3LYP method in gas-phase and water. Calculated results show that electron-withdrawing substituents increase the bond dissociation enthalpy (BDE), ionization potential (IP) and oxidation/reduction enthalpy (O/RE), while electron-donating ones cause a rise in the proton dissociation enthalpy (PDE) and proton affinity (PA). In ortho- position, substituents show larger effect on reaction enthalpies than in meta-position. In comparison to gas-phase, water attenuates the substituent effect on all reaction enthalpies. In gas-phase, BDEs are lower than PAs and IPs, i.e. HAT represents the thermodynamically preferred pathway. On the other hand, SPLET mechanism represents the thermodynamically favored process in water. Results show that calculated enthalpies can be successfully correlated with Hammett constants (${\sigma}_m$) of the substituted Magnolols. Furthermore, calculated IP and PA values for substituted Magnolols show linear dependence on the energy of the highest occupied molecular orbital ($E_{HOMO}$).
Keywords
Antioxidant; Magnolol; Solvent effect; Substituent effect;
Citations & Related Records

Times Cited By Web Of Science : 0  (Related Records In Web of Science)
연도 인용수 순위
  • Reference
1 Mulder, P.; Korth, H. G.; Pratt, D. A.; Dilabio, G. A.; Valgimigli, L.; Pedulli, G. F.; Ingold, K. U. J. Phys. Chem. A 2005, 109, 2647.   DOI   ScienceOn
2 Jackson, R. A.; Hosseini, K. M. J. Chem. Soc. Chem. Commun. 1992, 13, 967.
3 Patel, A.; Netscher, T.; Gille, L.; Mereiterd, K.; Rosenau, T. Tetrahedron 2007, 63, 5312.   DOI   ScienceOn
4 Tafazoli, S.; Wright, J. S.; O'Brien, P. J. Chem. Res. Toxicol. 2005, 18, 1567.   DOI   ScienceOn
5 Lee, S. B.; Lin, C. Y.; Gill, P. M. W.; Webster, R. D. J. Org. Chem. 2005, 70, 10466.   DOI   ScienceOn
6 Wilson, G. J.; Lin, C. Y.; Webster, R. D. J. Phys. Chem. B 2006, 110, 11540.   DOI   ScienceOn
7 Yamauchi, R.; Kato, K.; Ueno, Y. J. Agric. Food Chem. 1995, 43, 1455.   DOI   ScienceOn
8 Leopoldini, M.; Marino, T.; Russo, N.; Toscano, M. J. Phys. Chem. A 2004, 108, 4916.   DOI   ScienceOn
9 Espinosa-Garcia, J. Chem. Phys. Lett. 2004, 338, 274.
10 Guo, Y.; Zhu, Y.; Xue, Y.; Xie, D. Spectrochimica Acta Part A 2007, 68, 1287.   DOI   ScienceOn
11 Zhang, H. Y.; Ji, H. F. New J. Chem. 2006, 30, 503.   DOI   ScienceOn
12 Povalishev, V. N.; Polozov, G. I.; Shadyro, O. I. Bioorg. Med. Chem. Lett. 2006, 16, 1236.   DOI   ScienceOn
13 Singh, N. K.; O'Malley, P. J.; Popelier, P. L. A. J. Mol. Struct: Theochem. 2007, 811, 249.   DOI   ScienceOn
14 Wright, J. S.; Carpenter, D. J.; McKay, D. J.; Ingold, K. U. J. Am. Chem. Soc. 1997, 119, 4245.   DOI   ScienceOn
15 Setiadi, D. H.; Chass, G. A.; Torday, L. L.; Varro, A.; Papp, J. G. J. Mol. Struct.: Theochem. 2003, 637, 11.   DOI   ScienceOn
16 Wieser, H.; Vecchi, M.; Schlachter, M. Int. J. Vit. Nutr. Res. 1986, 56, 45.
17 Van Acker, S. A. B. E.; Koymans, L. M. H.; Bast, A. Free Radic. Biol. Med. 1993, 15, 311.   DOI   ScienceOn
18 Mukai, K.; Yokoyama, S.; Fukuda, K.; Uemoto, Y. Bull. Chem. Soc. Jpn. 1987, 60, 2163.   DOI
19 Burton, G. W.; Le Page, Y.; Gabe, E. J.; Ingold, K. U. J. Am. Chem. Soc. 1980, 102, 7791.   DOI
20 Najafi, M.; Nazarparvar, E.; Haghighi Mood, K.; Zahedi, M.; Klein, E. Comput. Theoret. Chem. 2011, 965, 114.   DOI   ScienceOn
21 Klein, E.; Rimarcik, J.; Lukes, V. Acta Chimica Slovaca 2009, 2, 37.
22 Becke, A. D. Chem. Phys. 1993, 98, 5648.
23 Becke, A. D. Phys. Rev. A 1988, 38, 3098.   DOI
24 Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.   DOI   ScienceOn
25 Davidson, E. R.; Feller, D. Chem. Rev. 1986, 86, 681.   DOI
26 Hehre, W. J.; Radom, L.; Schleyer, P. V. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986; p 226.
27 Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117.   DOI   ScienceOn
28 Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669.   DOI   ScienceOn
29 Bizarro, M. M.; Cabral, B. J. C.; dos Santos, R. M. B.; Simons, J. A. M. Pure Appl. Chem. 1999, 71, 1249.   DOI
30 Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowsk, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaroni, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzales, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M. R. E. S.; Pople, J. A. Gaussian 98, Gaussian, Inc., Pittsburgh, PA, 1998.
31 Bartmess, J. E. J. Phys. Chem. 1994, 98, 6420.   DOI   ScienceOn
32 Rimarcik, J.; Lukes, V.; Klein, E.; Ilcin, M. J. Mol. Struct.: Theochem. 2010, 952, 25.   DOI   ScienceOn
33 Nam, P. C.; Nguyen, M. T.; Chandra, A. K. J. Phys. Chem. A 2006, 110, 10904.   DOI   ScienceOn
34 Bordwell, F. G.; Zhang, X. M.; Satish, A. V.; Cheng, J. P. J. Am. Chem. Soc. 1994, 116, 6605.   DOI   ScienceOn
35 Brinck, T.; Haeberline, M.; Jonsson, M. J. Am. Chem. Soc. 1997, 119, 4239.   DOI   ScienceOn
36 de Heer, M. I.; Korth, H. G.; Mulder, P. J. Org. Chem. 1999, 64, 6969.   DOI   ScienceOn
37 Fu, Y.; Liu, R.; Liu, L.; Guo, Q. X. J. Phys. Org. Chem. 2004, 17, 282.   DOI   ScienceOn
38 Guerra, M.; Amorati, R.; Pedulli, G. F. J. Org. Chem. 2004, 69, 5460.   DOI   ScienceOn
39 Pratt, D. A.; Dilabio, G. A.; Mulder, P.; Ingold, K. U. Acc. Chem. Res. 2004, 37, 334.   DOI   ScienceOn
40 Zhu, Q.; Zhang, X. M.; Fry, A. J. Polym. Degrad. Stab. 1997, 57, 43.   DOI   ScienceOn
41 Berry, R. J.; Wilson, A. L.; Schwartz, M. J. Mol. Struct: Theochem. 2000, 496, 121.   DOI   ScienceOn
42 Leopoldini, M.; Pitarch, I. P.; Russo, N.; Toscano, M. J. Phys. Chem. A 2004, 108, 92.   DOI   ScienceOn
43 Najafi, M.; Zahedi, M.; Klein, E. Comput. Theoret. Chem. 2011, 978, 16.   DOI   ScienceOn
44 Klein, E.; Lukes, V.; Cibulkova, Z.; Polovkova, J. J. Mol. Struct: Theochem. 2006, 758, 149.   DOI   ScienceOn
45 Brinck, T.; Haeberline, M.; Jonsson, M. J. Am. Chem. Soc. 1997, 119, 4239.   DOI   ScienceOn
46 DiLabio, G. A.; Pratt, D. A.; Lofaro, A.D.; Wright, J. S. J. Phys. Chem. A 1999, 103, 1653.   DOI   ScienceOn
47 DiLabio, G. A.; Pratt, D. A.; Wright, J. S. Chem. Phys. Lett. 1999, 311, 215.   DOI   ScienceOn
48 DiLabio, G. A.; Pratt, D. A.; Wright, J. S. J. Org. Chem. 2000, 65, 2195.   DOI   ScienceOn
49 Migliavacca, E.; Carrupt, P. A.; Testa, B. Helv. Chim. Acta 1997, 80, 1613.   DOI   ScienceOn
50 Zhang, H. Y. J. Am. Oil. Chem. Soc. 1998, 75, 1705.   DOI   ScienceOn
51 Koopmans, T. Physica 1933, 1, 104.
52 Zhang, H. Y. J. Am. Oil. Chem. Soc. 1999, 76, 1109.   DOI
53 Kanchev, V. D.; Saso, L.; Boranova, P. V.; Khan, A.; Saroj, M. K.; Pandey, M. K.; Malhotra, S.; Nechev, J. Z.; Sharma, S. K.; Prasad, A. K.; Georgieva, M. B.; Joseph, C.; DePass, A. L.; Rastogi, R. C.; Parmar, V. S. Biochimie 2010, 92, 1089.   DOI   ScienceOn
54 Rimarcik, J.; Lukes, V.; Klein, E.; Rottmannova, L. Comput. Theoret. Chem. 2011, 967, 273.   DOI   ScienceOn
55 Lavarda, F. C. Int. J. Quant. Chem. 2003, 95, 219.   DOI   ScienceOn
56 Bi, W.; Bi, Y.; Xue, P.; Zhang, Y.; Gao, X.; Wang, Z.; Li, M.; Baudy-Floch, M.; Ngerebara, N.; Gibson, K. M.; Bi, L. J. Med. Chem. 2010, 53, 6763.   DOI   ScienceOn
57 Najafi, M.; Haghighi, Mood, K.; Zahedi, M.; Klein, E. Comput. Theoret. Chem. 2011, 969, 1.   DOI   ScienceOn
58 Dewar, M. J. S. The Molecular Orbital Theory of Organic Chemistry; McGraw-Hill: New York, 1969.
59 Matsui, N.; Nakashima, H.; Ushio, Y. Biol. Pharm. Bull. 2005, 28, 1762.   DOI   ScienceOn
60 Pryor, W. A. Free Radic. Biol. Med. 2000, 28, 141.   DOI   ScienceOn
61 Lin, Y. R.; Chen, H. H.; Ko, C. H.; Chan, M. H. Eur. J. Pharm. 2006, 537, 64.   DOI   ScienceOn
62 Chen, C. M.; Liu, S. H.; Lin-Shiau, S. Y. Basic and Clinical Pharmacology and Toxicology 2007, 101, 108.   DOI   ScienceOn
63 Matsui, N.; Takahashi, K.; Takeichi, M. Brain Research 2009, 1305, 108.   DOI   ScienceOn
64 Zhai, H.; Nakade, K.; Mitsumoto, Y.; Fukuyama, Y. Eur. J. Pharm. 2003, 474, 199.   DOI   ScienceOn
65 Chen, H. H.; Lin, S. C.; Chan M. H.; Neurodegenerative Diseases 2011, 8, 364.   DOI   ScienceOn
66 Fukuyama, Y.; Nakade, K.; Minoshima, Y.; Yokoyama, R.; Zhai, H.; Mitsumoto, Y. Bioorg. Med. Chem. Lett. 2002, 12, 1163.   DOI   ScienceOn
67 Zhai, H.; Nakade, K.; Oda, M. Eur. J. Pharm. 2005, 516, 112.   DOI   ScienceOn
68 Mori, A.; Ohashi, S.; Nakai, M.; Moriizumi, T.; Mitsumoto, Y. Neuroscience Research 2005, 51, 265.   DOI   ScienceOn
69 Wright, J. S.; Johnson, E. R.; Dilabio, G. A. J. Am. Chem. Soc. 2001, 123, 1173.   DOI   ScienceOn
70 Vafiadis, A. P.; Bakalbassis, E. G. Chem. Phys. 2005, 316, 195.   DOI   ScienceOn
71 Musialik, M.; Litwinienko, G. Org. Lett. 2005, 7, 4951.   DOI   ScienceOn
72 Zhang, H. Y.; Ji, H. F. J. Mol. Struct: Theochem. 2003, 663, 167.   DOI   ScienceOn
73 Zhang, H. Y.; Sun, Y. M.; Wang, X. L. J. Org. Chem. 2002, 67, 2709.   DOI   ScienceOn
74 Pratt, D. A.; Dilabio, G. A.; Brigati, G.; Pedulli, G. F.; Valgimigli, L. J. Am. Chem. Soc. 2001, 123, 4625.   DOI   ScienceOn
75 Burton, G. W.; Doba, T.; Gabe, E. J.; Hughes, L.; Lee, F. L.; Prasad, L.; Ingold, K. U. J. Am. Chem. Soc. 1985, 107, 7053.   DOI
76 Litwinienko, G.; Ingold, K. U. J. Org. Chem. 2003, 68, 3433.   DOI   ScienceOn
77 Litwinienko, G.; Ingold, K. U. J. Org. Chem. 2004, 69, 5888.   DOI   ScienceOn
78 Vianello, R.; Maksic, Z. B. Tetrahedron 2006, 62, 3402.   DOI   ScienceOn
79 Foti, M. C.; Daquino, C.; Geraci, C. J. Org. Chem. 2004, 69, 2309.   DOI   ScienceOn
80 Litwinienko, G.; Ingold, K. U. J. Org. Chem. 2005, 70, 8982.   DOI   ScienceOn
81 Fujio, M.; McIver, R. T., Jr.; Taft, R. W. J. Am. Chem. Soc. 1981, 103, 4017.   DOI
82 McMahon, T. B.; Kebarle, P. J. Am. Chem. Soc. 1977, 99, 2222.   DOI
83 Mulder, P.; Korth, H. G.; Ingold, K. U. Helv. Chim. Acta 2005, 88, 370.   DOI   ScienceOn
84 Wang, L. F.; Zhang, H. Y. Bioorg. Chem. 2005, 33, 108.   DOI   ScienceOn
85 Navarrete, M.; Rangel, C.; Corchado, J. C.; Espinosa-Garcia, J. J. Phys. Chem. A 2005, 109, 4777.   DOI   ScienceOn
86 Navarrete, M.; Rangel, C.; Espinosa-Garc a, J.; Corchado, J. C. J. Chem. Theory Comput. 2005, 1, 337.   DOI   ScienceOn
87 Wayner, D. D. M.; Lusztyk, E.; Ingold, K. U.; Mulder, P. J. Org. Chem. 1986, 61, 6430.
88 Nikolic, M. K. J. Mol. Struct: Theochem. 2007, 818, 141.   DOI   ScienceOn
89 Chen, W.; Song, J.; Guo, P.; Cao, W.; Bian, J. Bioorg. Med. Chem. Lett. 2006, 16, 5874.   DOI   ScienceOn
90 Lucarini, M.; Pederielli, P.; Pedulli, G. F.; Cabiddu, S.; Fattuoni, C. J. Org. Chem. 1996, 61, 9259.   DOI   ScienceOn
91 Klein, E.; Lukes, V.; Ilcin, M. Chem. Phys. 2007, 336, 51.   DOI   ScienceOn
92 Mohajeri, A.; Asemani, S. S. J. Mol. Struct: Theochem. 2009, 930, 15.   DOI   ScienceOn
93 Denisov, E. T. Polym. Degrad. Stab. 1995, 49, 71.   DOI   ScienceOn
94 Krygowski, T. M.; Steupien, B. T. Chem. Rev. 2005, 105, 3482.   DOI   ScienceOn
95 Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.   DOI
96 Zhu, Q.; Zhang, X. M.; Fry, A. J. Polym. Degrad. Stab. 1997, 57, 43.   DOI   ScienceOn
97 Bordwell, F. G.; Cheng, J. P. J. Am. Chem. Soc. 1991, 113, 1736.   DOI
98 Lind, J.; Shen, X.; Eriksen, T. E.; Merenyi, G. J. Am. Chem. Soc. 1990, 112, 479.   DOI
99 Klein, E.; Lukes, V. J. Phys. Chem. A 2006, 110, 12312.   DOI   ScienceOn
100 Chandra, A. K.; Uchimaru, T. Int. J. Mol. Sci. 2002, 3, 407.   DOI
101 Klein, E.; Lukes, V. J. Mol. Struct: Theochem. 2006, 767, 43.   DOI   ScienceOn
102 Klein, E.; Lukes, V. J. Mol. Struct: Theochem. 2007, 805, 153.   DOI   ScienceOn
103 Bakalbassis, E. G.; Lithoxoidou, A. T.; Vafiadis, A. P. J. Phys. Chem. A 2003, 107, 8594.   DOI   ScienceOn
104 Korth, H. G.; de Heer, M. I.; Mulder, P. J. Phys. Chem. A 2002, 106, 8779.   DOI   ScienceOn
105 Bakalbassis, E. G.; Lithoxoidou, A. T.; Vafiadis, A. P. J. Phys. Chem. A 2006, 110, 11151.   DOI   ScienceOn
106 Klein, E.; Lukes, V. Chem. Phys. 2006, 330, 515.   DOI   ScienceOn
107 Bosque, R.; Sales, J. J. Chem. Inf. Comput. Sci. 2003, 43, 637.   DOI   ScienceOn