Synthesis, Crystal Structure and Antimicrobial Activity of (E)-ethyl-4-(2-oxoacenaphthylen-1(2H)-ylideneamino) benzoate

Abstract

A Schiff base, (E)-ethyl-4-(2-oxoacenaphthylen-1(2H)-ylideneamino)benzoate, (E4AB) had been synthesized in good yield by the acid-catalyzed condensation reaction of acenaphthenequinone and ethyl-4-aminobenzoate in methanolic solution. The synthesized compound was elucidated by elemental analysis (CHN), FTIR, 1H-NMR, 13C-NMR and single crystal X-ray diffraction. E4AB crystallized in the monoclinic crystal system with space group P21/c, Z = 4, V = 1569.3(2) ?3 and unit cell parameters a = 9.1589(8) , b = 21.2003(17)?, c =8.4502(7) ?, β= 106.972(2)°. The crystal structure of the compound is stabilized by intermolecular C-H···O hydrogen bonds and weak intermolecular π···π interactions. The title compound had been tested for the antimicrobial activity against Bacillus subtilis (B. subtilis), Enterobacter and Fusarium oxysporum f. sp. Cubense (Foc) by disc-diffusion method. E4AB is relatively active against Foc which is a pathogen that cause Wilt disease (also well known as Panama disease) in banana plantation.

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Y. Chan, A. Ali, M. Khairuddean and B. Salleh, "Synthesis, Crystal Structure and Antimicrobial Activity of (E)-ethyl-4-(2-oxoacenaphthylen-1(2H)-ylideneamino) benzoate," Journal of Crystallization Process and Technology, Vol. 3 No. 2, 2013, pp. 69-73. doi: 10.4236/jcpt.2013.32011.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] R.-B. Xu, N. Zhang, H.-Y. Zhou, S. P. Yang, Y.-Y. Li, D.-H. Shi, W.-X. Ma and X.-Y. Xu, “Synthesis, Crystal Structure and Antibacterial Activity of N,N’-bis(4-metoxy-benzylidene)-1,4-bis(3-aminopropyl)piperazine,” Journal of Chemical Crystallography, Vol. 42, No. 9, 2012, pp. 928-932. doi:10.1007/s10870-012-0338-1
[2] L. G. Wade, “Organic Chemistry,” 6th Edition, Pearson Prentice Hall, Upper Saddle River, 2005.
[3] R. J. Maldanis, J. S. Wood, A. Chandrasekaran, M. D. Rausch and J. C. W. Chien, “The Formation and Polymerization Behaviour of Ni(II) α-Diimine Complexes Using Various Aluminium Activators,” Journal of Organometallic Chemistry, Vol. 645, No. 1-2, 2002, pp. 158-167. doi:10.1016/S0022-328X(01)01340-7
[4] I. Mhaidat, J. A. Mergos, S. Hamilakis, C. Kollia, Z. Loizos, A. Tsolomitis and C. T. Dervos, “One-Stage Synthesis of Poly[(p-phenylimino)-acenaphthene], a New Macromolecular Material with Interesting Electric Properties,” Materials Letters, Vol. 63, No. 29, 2009, pp. 2587- 2590. doi:10.1016/j.matlet.2009.09.016
[5] Y.-G. Li, L. Pan, Z.-J. Zheng and Y.-S. Li, “Polymerization of Ethylene to Branched Polyethylene with Silica and Merrifield Resin Supported Nickel(II) Catalysts with α-Diimine Ligands,” Journal of Molecular Catalysis A: Chemical, Vol. 287, No. 1-2, 2008, pp. 57-64. doi:10.1016/j.molcata.2008.03.003
[6] G. W. Son, K. B. Bijal, D. W. Park, C. S. Ha and I. L. Kim, “Novel Nickel(II)-Based Catalysts for the Polymerization of Ethylene,” Catalysis Today, Vol. 111, No. 3-4, 2006, pp. 412-416. doi:10.1016/j.cattod.2005.10.054
[7] M. C. Rodriguez-Argüelles, M. B. Ferrari, G. G. Fava, C. Pelizzi, G. Pelosi, R. Albertini, A. Bonati, P. P. Dall’ Aglio, P. Lunghi and S. Pinelli, “Acenaphthenequinone Thiosemicarbazone and Its Transition Metal Complexes: Synthesis, Structure, and Biological Activity,” Journal of Inorganic Biochemistry, Vol. 66, No. 1, 1997, pp. 7-17. doi:10.1016/S0162-0134(96)00146-8
[8] U. El-Ayaan, and A. A. M. Abdel-Aziz, “Synthesis, Antimicrobial Activity and Molecular Modelling of Cobalt and Nickel Complexes Containing the Bulky Ligand: Bis[N-(2,4-diisopropylphenyl)imino]acenaphthene,” Eur- opean Journal of Medicinal Chemistry, Vol. 40, No. 12, 2005, pp. 1214-1221. doi:10.1016/j.ejmech.2005.06.009
[9] P. L. Ooi and K. T. Goh, “Sick Building Syndrome: An Emerging Stress-Related Disorder,” International Journal of Epidemiology, Vol. 26, No. 6, 1997, pp. 1243-1249. doi:10.1093/ije/26.6.1243
[10] M. J. Mendell, W. J. Fisk, K. Kreiss, H. Levin, D. Alexander, W. S. Cain, J. R. Girman, C. J. Hines, P. A. Jensen, D. K. Milton, L. P. Rexroat and K. M. Wallingford, “Improving the Health of Workers in Indoor Environments: Priority Research Needs for a National Occupational Research Agenda,” American Journal of Public Health, Vol. 92, No. 9, 2002, pp. 1430-1440. doi:10.2105/AJPH.92.9.1430
[11] Jumjunidang, Riska and A. Soemargono, “Identification and Distribution of Fusarium Oxysporum f. sp. Cubense Isolates through Analysis of Vegetative Compatibility Group in Lampung Province, Indonesia,” Journal of Engineering and Applied Sciences, Vol. 7, No. 4, 1990, pp. 279-284.
[12] J. Cosier and A. M. Glazer, “A Nitrogen-Gas-Stream Cryostat for General X-Ray Diffraction Studies,” Journal of Applied Crystallography, Vol. 19, No. 2, 1986, pp. 105-107. doi:10.1107/S0021889886089835
[13] Bruker, “APEX2, SAINT and SADABS,” Bruker AXS Inc., Madison, 2009.
[14] G. M. Sheldrick, “A Short History of SHELX,” Acta Crystallographica Section A, Vol. 64, No. 1, 2008, pp. 112-122. doi:10.1107/S0108767307043930
[15] R. P. Murray, E. J. Baron, M. A. Pfaller, F. C. Tenover, and R. H. Yolken, “Manual of Clinical Microbiology,” 6th Edition, ASM Press, Washington DC, 1995.
[16] J. Kovach, M. Peralta, W. W. Brennessel and W. D. Jones, “Synthesis and X-Ray Crystallographic Characterization of Substituted Aryl Imines,” Journal of Molecular Structure, Vol. 992, No. 1-3, 2011, pp. 33-38. doi:10.1016/j.molstruc.2011.02.027
[17] K. M. El-Shaieb, “Condensation of 1-(Dicycanomethylene)acenaphthene-2-one with Aromatic Diamines,” Journal of the Chinese Chemical Society, Vol. 55, No. 5, 2008, pp. 1150-1155.
[18] X. Y. Wang, J. N. Cui, W. M. Ren, F. Li, C. L. Lu and X. H. Qian, “Baker’s Yeast Mediated Reduction of Substituted Acenaphthenequinones: Regio and Eneatioselective Preparation of Mono-Hydroxyacenaphthenones,” Chinese Chemical Letters, Vol. 18, No. 6, 2007, pp. 681-684. doi:10.1016/j.cclet.2007.04.022
[19] W. Yang, Z. Yin, Z. Li, J. He and J.-P. Cheng, “A New Acenaphthenequinone-Based Calyx[4]pyrrole: Synthesis, Structure and Anion Binding Study,” Journal of Molecular Structure, Vol. 889, No. 1-3, 2008, pp. 279-285. doi:10.1016/j.molstruc.2008.02.014

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