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Vol. 26 No. 18 (2014): Vol 26 Issue 18

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Synthesis, Crystal Structure and Quantum Chemistry Calculation of Two Novel Compounds Derived from Amino-Phenol

https://doi.org/10.14233/ajchem.2014.17103
Pengfei Zhang
Key Laboratory of Marine Chemistry Theory and Technology, Ministry of Education, College of Chemistry and Chemical Engineering, Ocean University of China, 238 Songling Road, Qingdao 266100, Shandong Province, P.R. China
Yuhua Fan
Key Laboratory of Marine Chemistry Theory and Technology, Ministry of Education, College of Chemistry and Chemical Engineering, Ocean University of China, 238 Songling Road, Qingdao 266100, Shandong Province, P.R. China
Caifeng Bi
Key Laboratory of Marine Chemistry Theory and Technology, Ministry of Education, College of Chemistry and Chemical Engineering, Ocean University of China, 238 Songling Road, Qingdao 266100, Shandong Province, P.R. China
Xia Zhang
Key Laboratory of Marine Chemistry Theory and Technology, Ministry of Education, College of Chemistry and Chemical Engineering, Ocean University of China, 238 Songling Road, Qingdao 266100, Shandong Province, P.R. China
Xingchen Yan
Key Laboratory of Marine Chemistry Theory and Technology, Ministry of Education, College of Chemistry and Chemical Engineering, Ocean University of China, 238 Songling Road, Qingdao 266100, Shandong Province, P.R. China
Xiaojing Wu
Key Laboratory of Marine Chemistry Theory and Technology, Ministry of Education, College of Chemistry and Chemical Engineering, Ocean University of China, 238 Songling Road, Qingdao 266100, Shandong Province, P.R. China

Corresponding Author(s) : Yuhua Fan

fanyuhua301@163.com

Asian Journal of Chemistry, Vol. 26 No. 18 (2014): Vol 26 Issue 18

Abstract

Two novel compounds [(Z)-3-(2-hydroxy-4-methylphenylimino)indolin-2-one][methanol] (A) and 4-[(Z)-(3-hydroxy-4-methoxyphenylimino)(phenyl)methyl]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one (B) derived from amino-phenol were synthesized and characterized by IR spectroscopy, elemental analysis and X-ray diffraction single-crystal analysis. Compound A crystallizes in monoclinic space group P21/c with a = 15.6637 (12) Å, b =12.3527 (9) Å, c = 7.4461 (6) Å, a = 90º, b = 100.9460 (10) º, g = 90º, V = 1414.53 (19) nm3, Z = 4, F (000) = 600, S = 1.055, R1 = 0392, wR2 = 0.0967. In addition, compound B crystallizes in triclinic, space group P-1 with a = 8.8111 (9) Å, b = 11.4716 (12) Å, c =11.4947 (14) Å, a = 115.376 (2) º, b = 99.5470 (10) º, g = 97.6320 (10) º, V = 1007.74 (19) nm3, Z = 2, F (000) = 420, S = 1.046, R1 = 0.0643, wR2 = 0.1479. Theoretical studies of compounds A and B were carried out by density functional theory B3LYP method. The results show that N (1), O (1) and O (2) of compound A and N (3), O (1) and O (2) of compound B are major active sites. Furthermore, N (1) in compound A is preferentially attacked by nucleophilic, followed by the N (3) in compound B. The theoretical studies show that compound A may have higher biological activity, such as anti-proliferative activity, compared with compound B. The result may be because that compound A is Schiff base and compound B occur proton transfer and tautomerism. CCDC: Compound A: 850318, Compound B: 938243.

Keywords

Crystal structure Amino-phenol Tautomerism Quantum chemistry calculation Anti-proliferative activity
Zhang, P., Fan, Y., Bi, C., Zhang, X., Yan, X., & Wu, X. (2014). Synthesis, Crystal Structure and Quantum Chemistry Calculation of Two Novel Compounds Derived from Amino-Phenol. Asian Journal of Chemistry, 26(18), 6176–6184. https://doi.org/10.14233/ajchem.2014.17103
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References
  1. S.C. Chandar, K. Santhakumar and M.N. Arumugham, Transition Met. Chem., 34, 841 (2009); doi:10.1007/s11243-009-9272-2.
  2. D.H.R. Barton and W.D. Ollis, Comprehensive Organic Chemistry, vol. 2, p. 500, Pergamon, Oxford (1979).
  3. H. Tanak, A.A. Agar and O. Buyukgungor, J. Mol. Struct., 1048, 41 (2013); doi:10.1016/j.molstruc.2013.05.014.
  4. G. Anbarasu, C. Srividhya, P. Maheswaran and R. Rajavel, J. Appl. Chem., 2, 1315 (2013).
  5. A.L. Wolfe, K.K. Duncan, N.K. Parelkar, D. Brown, G.A. Vielhauer and D.L. Boger, J. Med. Chem., 56, 4104 (2013); doi:10.1021/jm400413r.
  6. P.S. Patel, Arch. Appl. Sci. Res., 4, 846 (2012).
  7. G. Thenmozhi, K.D. Jaya, M. Gopalswamy and S.R. Jaya, Pharma Chemica, 3, 325 (2011).
  8. D.M. Aysen, O. Birol and M. Bedrettin, Int. J. Drug Dev. Res., 2, 102 (2010).
  9. S.A. Joshi and A.G. Mehta, Orient. J. Chem., 20, 173 (2004).
  10. S.Y. Zhang, P.P. Jiang and Y.C. Yan Leng, Chem. J. Chinese Univ., 34, 1703 (2013).
  11. M. Jesmin, M.M. Ali and J.A. Khanam, Thai J. Pharm. Sci., 34, 20 (2010).
  12. X. Chen, J.Q. Lei, Z.Y. Wang and Y.C. Zhang, J. Lanzhou Univ., 33, 16 (2007).
  13. T.M. Yang, S.F. Guo, C.R. Chen, X.Y. Zhang and W.G. Li, J. Pharm. Pharmacol., 60, 179 (2008); doi:10.1211/jpp.60.2.0006.
  14. C.K. Lam and T.C.W. Mak, Tetrahedron, 56, 6657 (2000); doi:10.1016/S0040-4020(00)00473-7.
  15. C.B. Aakeroy and K.R. Seddon, Chem. Soc. Rev., 22, 397 (1993); doi:10.1039/cs9932200397.
  16. X.C. Yan, Y.H. Fan, C.F. Bi, X. Zhang and Z.Y. Zhang, Acta Crystallogr., 69C, 61 (2013); doi:10.1107/S0108270112047877.
  17. T. Ziegler, Chem. Rev., 91, 651 (1991); doi:10.1021/cr00005a001.
  18. A. Coruh, F. Yilmaz, B. Sengez, M. Kurt, M. Cinar and M. Karabacak, Struct. Chem., 22, 45 (2011); doi:10.1007/s11224-010-9694-7.
  19. C. Hemmert, R. Poteau, M. Laurent and H. Gornitzka, J. Organomet. Chem., 745-746, 242 (2013); doi:10.1016/j.jorganchem.2013.07.082.
  20. S.O. Jung, Y.J. Kang, H.S. Kim, Y.H. Kim, K.Y. Yang and S.K. Kwon, Bull. Korean Chem. Soc., 24, 1521 (2003); doi:10.5012/bkcs.2003.24.10.1521.
  21. M. Karabacak, M. Cinar and M. Kurt, Spectrochim. Acta A, 74, 1197 (2009); doi:10.1016/j.saa.2009.09.035.
  22. S. Patchkovskii and T. Ziegler, J. Phys. Chem., 105, 5490 (2001); doi:10.1021/jp010457a.
  23. S.B. Liu, C.F. Bi, Y.H. Fan, J. Zuo, X.Y. Liu and Y.P. Zheng, Chinese J. Struct. Chem., 30, 887 (2011).
  24. S.W. Xia, X. Xu, Y.L. Sun, Y.H. Fan and C.F. Bi, Chinese J. Struct. Chem., 25, 198 (2006).
  25. M. Dong, H.L. Zhu, X. Zhang and H.Z. Xu, Chinese J. Tianjin Normal Univ., 25, 13 (2005).
  26. A.D. Wang, C.F. Bi, Y.H. Fan, Y.N. Zou, J.K. Xu and Y.H. Kan, Russ. J. Coord. Chem., 34, 475 (2008); doi:10.1134/S1070328408070014.
  27. N. Okulik and A.H. Jubert, Internet Electron. J. Mol. Des., 4, 17 (2005).
  28. P. Politzer, P.R. Laurence, K. Jayasuriya and J. McKinney, Environ. Health Perspect., 61, 191 (1985); doi:10.1289/ehp.8561191.
  29. J. Zuo, C. Bi, Y. Fan, D. Buac, C. Nardon, K.G. Daniel and Q.P. Dou, J. Inorg. Biochem., 118, 83 (2013); doi:10.1016/j.jinorgbio.2012.10.006.
  30. M. Groll, L. Ditzel, J. Lowe, D. Stock, M. Bochtler, H.D. Bartunik and R. Huber, Nature, 386, 463 (1997); doi:10.1038/386463a0.
  31. R. Anbazhagan and K.R. Sankaran, J. Mol. Struct., 1050, 73 (2013); doi:10.1016/j.molstruc.2013.07.019.
  32. J. Jayabharathi, V. Thanikachalam and K. Jayamoorthy, Spectrochim. Acta A, 115, 74 (2013); doi:10.1016/j.saa.2013.06.001.
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