European Journal of Chemistry

Synthesis, characterization and crystal structure of 2-(4-(methylthio)phenyl)-1H-benzo[d]imidazole

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Published: Mar 28, 2011
DOI: https://doi.org/10.5155/eurjchem.2.1.58-60.350
Keywords:
2-(4-(methylthio)phenyl)-1H-benzo[d]imidazole, Benzimidazole, Crystal structure, Hydrogen bond, pi-pi Interactions, Spectroscopy
Section
Research Article
Issue
Vol. 2 No. 1 (2011): March 2011
Dates
Received 2010-11-25
Accepted 2010-12-05
Published 2011-03-28


Main Article Content

Mohamed Ziaulla
Department of Chemistry, Bangalore University, Bangalore, IN-560001, India
Maralavadi Nagaraju Manjunatha
Department of Chemistry, Bangalore University, Bangalore, IN-560001, India
Kuderu Rajendraswamy Nagasundara
Department of Chemistry, Bangalore University, Bangalore, IN-560001, India
Noor Shahina Begum
Department of Chemistry, Bangalore University, Bangalore, IN-560001, India

Abstract

An efficient synthesis of the title compound, 2-(4-(methylthio)phenyl)-1H-benzo[d]imidazole, was carried out by the condensation reaction of o-phenylenediamine and p-thiomethyl benzaldehyde in benzene. The structure was confirmed by spectroscopic data and elemental analyses. The molecular structure was determined from single crystal X‐ray diffraction data. The compound crystallizes in the orthorhombic space group Pbca with a = 8.544(2) Å, b = 9.700(3) Å, c = 29.684(8) Å, V = 2460.0(11) Å3, Z = 8. The crystal structure is stabilized by intermolecular C-H…N, N-H…N and π-π interactions.

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Ziaulla, M.; Manjunatha, M. N.; Nagasundara, K. R.; Begum, N. S. Synthesis, Characterization and Crystal Structure of 2-(4-(methylthio)phenyl)-1H-benzo[d]imidazole. Eur. J. Chem. 2011, 2, 58-60.

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References

[1]. Al Muhaimeed, H. J. Int. Med. Res. 1997, 25, 175-181.

[2]. Scott, L. J.; Dunn, C. J.; Mallarkey, G.; Sharpe, M. Drugs 2002, 62, 1503-1538.
doi:10.2165/00003495-200262100-00006
PMid:12093317

[3]. Nakano, H.; Inoue, T.; Kawasaki, N.; Miyataka, H.; Matsumoto, H.; Taguchi, T.; Inagaki, N.; Nagai, H; Satoh, T. Bioorg. Med. Chem. 2000, 8, 373-380.
doi:10.1016/S0968-0896(99)00291-6

[4]. Cohn, G. Ber. 1899, 32, 2239-2242.
doi:10.1002/cber.189903202152

[5]. Zhu, Z.; Lippa, B.; Drach, J. C.; Townsend, L. B. J. Med. Chem. 2000, 43, 2430-2437.
doi:10.1021/jm990290y
PMid:10882370

[6]. Zarrinmayeh, H.; Nunes, A. M.; Ornstein, P. L.; Zimmerman, D. M.; Arnold, M. B.; Schober, D. A.; Gackenheimer, S. L.; Bruns, R. F.; Hipskind, P. A.; Britton, T. C.; Cantrell, B. E.; Gehlert, D. R. J. Med. Chem. 1998, 41, 2709-2719.
doi:10.1021/jm9706630
PMid:9667962

[7]. Preston, P. N. Chem. Rev. 1974, 74, 279-314.
doi:10.1021/cr60289a001

[8]. Huang, W.; Scarborough, R. M. Tetrahedron Lett. 1999, 40, 2665-2668.
doi:10.1016/S0040-4039(99)00293-2

[9]. Kilburn, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron Lett. 2000, 41, 5419-5421.
doi:10.1016/S0040-4039(00)00871-6

[10]. Tumelty, D.; Cao, K.; Holmes, C. P. Org. Lett. 2001, 3, 83-86.
doi:10.1021/ol006801o
PMid:11429878

[11]. Dudd, L. M.; Venardou, E.; Garcia-Verdugo, E.; Licence, P.; Blake, A. J.; Wilson, C.; Poliakoff, M. Green Chem. 2003, 5, 187-192.
doi:10.1039/b212394k

[12]. Perumal, S.; Mariappan, S.; Selvaraj, S. Arkivoc 2004, 8, 46-51.

[13]. Trivedi, R.; De, S. K.; Gibbs, R. A. J. Mol. Catal. A: Chem. 2006, 8, 245-248.

[14]. Oskooie, H. A.; Heravi, M. M.; Sadnia, A.; Behbahani, F. K.; Jannati, F. Chin. Chem. Lett. 2007, 18, 1357-1360.

[15]. Landge, S. M.; Török, B. Catal. Lett. 2008, 122, 338-343.
doi:10.1007/s10562-007-9385-1

[16]. Salehi, P.; Dabiri, M.; Zolfigol, M. A.; Otokesh, S.; Baghbanzadeh, M. Tetrahedron Lett. 2006, 47, 2557-2560.
doi:10.1016/j.tetlet.2006.02.049

[17]. Ravi, V.; Ramu, E.; Vijay, K.; Rao, A. S. Chem. Pharm. Bull. 2007, 55, 1254-1257.
doi:10.1248/cpb.55.1254

[18]. Perry, R. J.; Wilson, B. D. J. Org. Chem. 1993, 58, 7016-7021.
doi:10.1021/jo00077a019

[19]. Bruker. 1998, SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

[20]. Sheldrick, G. M. Acta Cryst. 2008, A64, 112–122.

[21]. Farrugia, L. J. ORTEP-3. J. Appl. Cryst. 1999, 32, 837–838.
doi:10.1107/S0021889899006020

[22]. Nardelli, M. Acta Cryst. 1983, C39, 114-114.

[23]. Etter, M. C. J. Phys. Chem. 1991, 95, 4601-4610.
doi:10.1021/j100165a007

[24]. Etter, M. C. Acc. Chem. Res. 1990, 23, 120-126.
doi:10.1021/ar00172a005

[25]. Goker, H.; Olgen, S.; Ertan, R.; Akgiin, H.; Ozbey, S.; Kendi, E.; Topcu, G. . J. Heterocyl. Chem. 1995, 32, 1767-1773.
doi:10.1002/jhet.5570320617

[26]. Ozbey, S.; Ide, S.; Kendi, E. J. Mol. Struct. 1998, 442, 23-25.
doi:10.1016/S0022-2860(97)00087-2

[27]. Eryigit, R.; Kendi, E. J. Chem. Crystallogr. 1998, 28, 145-147.
doi:10.1023/A:1022497931783

[28]. Kendi, E.; Ozbey, S.; Tuncbilek, M.; Goker, H. Acta Crystallogr. 1998, C54, 854-856.

[29]. Vasudevan, K. T.; Puttaraja, K. A.; Kulkarni, M. V. Acta Crystallogr. 1994, C50, 1286-1288.

[30]. Elerman, Y.; Kabak, M. Acta Crystallogr. 1997, C53, 372-374.

[31]. Balasubramanian, T.; Viswanathan, R.; Palaniandavar, M.; Muthiah P. J. Chem. Crystallogr. 1996, 26, 457-460.
doi:10.1007/BF01668304

Supporting Agencies

University Grants Commission (UGC), India for the financial assistance and Department of Science and Technology (DST), India for data collection.
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