European Journal of Chemistry

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



Main Article Content

Mohamed Ziaulla
Maralavadi Nagaraju Manjunatha
Kuderu Rajendraswamy Nagasundara
Noor Shahina Begum

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.

2_1_58_60_800


icon graph This Abstract was viewed 1395 times | icon graph Article PDF downloaded 687 times icon graph Article CIF FILE downloaded 0 times

How to Cite
(1)
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.

Article Details

Share
Crossref - Scopus - Google - European PMC
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

Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).