Synthesis, spectral analysis, X-ray crystal structures and evaluation of chemical reactivity of five new benzoindazole derivatives through experimental and theoretical studies

Journal of Molecular Structure

Volumn 1076, Issue , 2014, Pages 272-279

  Taib, Layla A ^a   Faidallah, Hassan M ^a   Şahin, Zarife Sibel ^b   Asiri, Abdullah M ^a   Şahin, Onur ^b   Arshad, Muhammad Nadeem ^a  

^a KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

^b SINOP UNIVERSITY   (Turkey)

Author keywords

Chemical reactivity; DFT; Molecular electrostatic potential; X ray Benzoindazole

Indexed keywords

DFT; MOLECULAR ELECTROSTATIC POTENTIALS; THEORETICAL STUDY; X RAY CRYSTAL STRUCTURES;

CHEMICAL REACTIVITY;

EID: 84906961200     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2014.07.033     Document Type: Article

References (50)

1. H. Cerecetto, A. Gerpe, M. González, V.J. Arán, and C.O. de Ocáriz Mini-Rev. Med. Chem. 5 2005 69 878
2. M. De Angelis, F. Stossi, K.A. Carlson, B.S. Katzenellenbogen, and J.A. Katzenellenbogen J. Med. Chem. 48 2005 1132 1144
3. H.C. Zhang, C.K. Derian, D.F. McComsey, K.B. White, H. Ye, L.R. Hecker, J. Li, M.F. Addo, D. Croll, A.J. Eckardt, C.E. Smith, Q. Li, W.M. Cheung, B.R. Conway, S. Emanuel, K.T. Demarest, P. Andrade-Gordon, B.P. Damiano, and B.E. Maryanoff J. Med. Chem. 48 2005 1725 1728
4. J.A. May, A.P. Dantanarayana, P.W. Zinke, M.A. McLaughlin, and N.A. Sharif J. Med. Chem. 49 2006 318 328
5. W. Han, J.C. Pelletier, and C.N. Hodge Bioorg. Med. Chem. Lett. 8 1998 3615 3620
6. H.D. Showalter, M.M. Angelo, E.M. Berman, G.D. Kanter, D.F. Ortwine, S.G. Ross-Kesten, A.D. Sercel, W.R. Turner, L.M. Werbel, D.F. Worth, E.F. Elslager, W.R. Leopald, and J.L. Shillis J. Med. Chem. 31 1988 1527 1539
7. A. Gugliemotti, A. Capezzone de Joannon, N. Cazzolla, M. Marchetti, L. Soldo, G. Cavallo, and M. Pinza Pharmacol. Res. 32 1995 369 373
8. R. Makino, E. Obayashi, N. Homma, Y. Shiro, and H. Hori J. Biol. Chem. 278 2003 11130 11137
9. R.M. Claramunt, C. López, C. Pérez-Medina, M. Pérez-Torralba, J. Elguero, G. Escames, and D. Acuña-Castroviejo Bioorg. Med. Chem. 17 2009 6180 6187
10. J. Elguero, I. Alkorta, R.M. Claramunt, C. López, D. Sanz, and D.S. María Bioorg. Med. Chem. 17 2009 8027 8031.
11. L. Ravagnan, I. Marzo, P. Costantini, S.A. Susin, N. Zamzami, P.X. Petit, F. Hirsch, M. Goulbern, M.F. Poupon, L. Miccoli, Z. Xie, J.C. Reed, and G. Kroemer Oncogene 18 1999 2537 2546
12. J.B. Foresman, and A. Frisch Exploring Chemistry with Electronic Structure Methods 1996 Gaussian Inc. Pittsburgh, USA
13. D.S. Sholl, and J.A. Steckel Density Functional Theory, A Practical Introduction 2009 Wiley New Jersey
14. H.M. Faid-Allah, and M.S. Makki J. Chin. Chem. Soc. 41 1994 585 589
15. G.M. Sheldrick Acta Cryst. A64 2008 112 122
16. L.J. Farrugia J. Appl. Cryst. 32 1999 837 838
17. Mercury, version 3.0; CCDC, Available online via ccdc.cam.ac.uk/products/mercury.
18. A.L. Spek PLATON - A Multipurpose Crystallographic Tool 2005 Utrecht University Utrecht
19. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., J.T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, 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, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A. D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Lui, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W.B. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, GAUSSIAN 03, Revision C.02, Gaussian Inc., Wallingford CT, 2004.
20. A. Frisch, R.D. Dennington II, T.A. Keith, J. Milliam, A.B. Nielsen, A.J. Holder, and J. Hiscocks GaussView Reference, Version 4.0 2007 Gaussian Inc. Pittsburgh
21. P. Hohenberg, and W. Kohn Phys. Rev. 136 1964 B846 B871
22. W. Kohn, and L.J. Sham Phys. Rev. 140 1965 A1133 1138
23. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
24. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B37 1988 785 789
25. R. Ditchfield, W.J. Hehre, and J.A. Pople J. Chem. Phys. 54 1971 724 728
26. C. Peng, P.Y. Ayala, H.B. Schlegel, and M.J. Frisch J. Comput. Chem. 17 1996 49 50
27. P.J. Stephens, F.J. Devlin, C.F. Chablowski, and M.J. Frisch J. Phys. Chem. 98 1994 11623 11627
28. R. Ditchfield J. Chem. Phys. 56 1972 5688 5692
29. J.K. Wolinski, J.F. Hinton, and P. Pulay J. Am. Chem. Soc. 112 1990 8251 8260
30. M.J. Meyers, G.B. Arhancet, S.L. Hockerman, Xiangyang Chen, S.A. Long, M.W. Mahoney, J.R. Rico, D.J. Garland, J.R. Blinn, J.T. Collins, Shengtian Yang, Horng-Chih Huang, K.F. McGee, J.M. Wendling, J.D. Dietz, M.A. Payne, B.L. Homer, M.I. Heron, D.B. Reitz, and Xiao Hu J. Med. Chem. 53 2010 5979 6002.
31. S. Choi, H. Keys, R.J. Staples, Junying Yuan, A. Degterev, and G.D. Cuny Bioorg. Med. Chem. Lett. 22 2012 5685 5688.
32. E. Klimova, T. Klimova, T.R. Apan, A.N. Camacho, R.M. Esparza, C.D. Zea, and M.M. Garcia Heterocycles 63 2004 1045 1056
33. E.O. Oloo, K. Nienaber, J.W. Quail, M.P. Padmanilayam, U. Das, and J.R. Dimmock Acta Crystallogr. E60 2004 o610 o612
34. J.P. Merrick, D. Moran, and L. Radom J. Phys. Chem. A 111 2007 11683 11700
35. H.A. Dabbagh, A. Teimouri, A.N. Chermahini, and M. Shahraki Spectrochim. Acta A 69 2008 449 459.
36. R.R. Saravanan, S. Seshadri, S. Gunasekaran, R. Mendoza-Merono, and S. Garcia-Granda Spectrochim. Acta A 121 2014 268 275
37. P. Politzer, and K.C. Daiker Models for chemical reactivity The Force Concept in Chemistry 1981 Van Nostrand Reinhold New York
38. S.R. Cox, and D.E. Williams J. Comput. Chem. 2 1981 304 323
39. R. Carbo, and B. Calabuig Comput. Phys. Commun. 55 1989 117 126
40. P. Politzer, and P. Lane Struct. Chem. 1 1990 159 164
41. P. Politzer, and D.G. Truhlar Chemical Applications of Atomic and Molecular 1981 Electrostatic Potentials Plenum New York
42. E. Scrocco, and J. Tomasi Top. Curr. Chem. 42 1973 95 170
43. I. Fleming Frontier Orbitals and Organic Chemical Reactions 1976 Wiley London
44. E. Kavitha, N. Sundaraganesan, and S. Sebastian Indian J. Pure Appl. Phys. 48 2010 20 30
45. K.H. Kim, Y.K. Han, and J. Jung Theor. Chem. Acc. 113 2005 233 237
46. J. Aihara J. Phys. Chem. A 103 1999 7487 7495
47. R.G. Pearson J. Chem. Sci. 117 2005 369 377
48. P.G. Parr, and R.G. Pearson J. Am. Chem. Soc. 105 1983 7512 7516
49. A.M. Charles J. Chem. Sci. 123 2011 727 731
50. P.K. Chattaraj, and B. Maiti J. Am. Chem. Soc. 125 2003 2705 2710