Theoretical Study on the Mechanism of Synthesis of 2-(p-tolyl)-1H-benzo[d]imidazole

Qi-Shan Hu; Yun-Qing He; Lai-Cai Li

doi:10.14233/ajchem.2014.16383

Issue

Vol. 26 No. 19 (2014): Vol 26 Issue 19

Issue Published : September 16, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Theoretical Study on the Mechanism of Synthesis of 2-(p-tolyl)-1H-benzo[d]imidazole

https://doi.org/10.14233/ajchem.2014.16383

Qi-Shan Hu

College of Chemistry and Chemical Engineering, Sichuan University of Arts and Science, Dazhou 635711, P.R. China

Yun-Qing He

College of Chemistry and Chemical Engineering, Sichuan University of Arts and Science, Dazhou 635711, P.R. China

Lai-Cai Li

College of Chemistry and Material Science, Sichuan Normal University, Chengdu 610066, P.R. China

Corresponding Author(s) : Qi-Shan Hu

huqs@163.com

Asian Journal of Chemistry, Vol. 26 No. 19 (2014): Vol 26 Issue 19
Article Published : September 18, 2014

Abstract

The mechanism of one-pot synthesis among benzene-1,2-diamine, isothiocyanatomethane and 4-methylbenzaldehyde for the synthesis of 2-(p-tolyl)-1H-benzo[d]imidazole was investigated by density functional theory (DFT). The geometries and the frequencies of reactants, intermediates, transition states and products were calculated at the B3LYP/6-311G(d) level. The vibration analysis and the IRC analysis verified the authenticity of transition states. The reaction processes were confirmed by the changes of charge density at the bond-forming critical point. The results indicated that (1) IM2C ® IM2D is rate-determining step; (2) The activation energy of the reaction is 351.53 Kj mol^-1.

Keywords

Density functional theory 2-(p-tolyl)-1H-benzo[d]imidazole One-pot synthesis Transition state Reaction mechanism

Hu, Q.-S., He, Y.-Q., & Li, L.-C. (2014). Theoretical Study on the Mechanism of Synthesis of 2-(p-tolyl)-1H-benzo[d]imidazole. Asian Journal of Chemistry, 26(19), 6387–6390. https://doi.org/10.14233/ajchem.2014.16383

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References

R.V. Shingalapur, K.M. Hosamani and R.S. Keri, Eur. J. Med. Chem., 44, 4244 (2009); doi:10.1016/j.ejmech.2009.05.021.
D. Zampieri, M.G. Mamolo, L. Vio, E. Banfi, G. Scialino, M. Fermeglia, M. Ferrone and S. Pricl, Bioorg. Med. Chem., 15, 7444 (2007); doi:10.1016/j.bmc.2007.07.023.
A. Puratchikody and M. Doble, Bioorg. Med. Chem., 15, 1083 (2007); doi:10.1016/j.bmc.2006.10.025.
K.C.S. Achar, K.M. Hosamani and H.R. Seetharamareddy, Eur. J. Med. Chem., 45, 2048 (2010); doi:10.1016/j.ejmech.2010.01.029.
P. Gupta, S. Hameed and R. Jain, Eur. J. Med. Chem., 39, 805 (2004); doi:10.1016/j.ejmech.2004.05.005.
F. Hadizadeh, H. Hosseinzadeh, V. Sadat Motamed-Shariaty, M. Seifi, S. Kazemi, Iran. J. Pharm. Res., 7, 29 (2008).
H.M. Refaat, Eur. J. Med. Chem., 45, 2949 (2010); doi:10.1016/j.ejmech.2010.03.022.
D. Sharma, B. Narasimhan, P. Kumar, V. Judge, R. Narang, E. De Clercq and J. Balzarini, Eur. J. Med. Chem., 44, 2347 (2009); doi:10.1016/j.ejmech.2008.08.010.
K. Bhandari, N. Srinivas, V.K. Marrapu, A. Verma, S. Srivastava and S. Gupta, Bioorg. Med. Chem. Lett., 20, 291 (2010); doi:10.1016/j.bmcl.2009.10.117.
S. Balalaie and A. Arabanian, Green Chem., 2, 274 (2000); doi:10.1039/b006201o.
S. Samai, G.C. Nandi, P. Singh and M.S. Singh, Tetrahedron, 65, 10155 (2009); doi:10.1016/j.tet.2009.10.019.
A. Hasaninejad, A. Zare, M. Shekouhy and J. Ameri Rad, J. Comb. Chem., 12, 844 (2010); doi:10.1021/cc100097m.
A. Davoodnia, M.M. Heravi, Z. Safavi-Rad and N. Tavakoli-Hoseini, Synth. Commun., 40, 2588 (2010); doi:10.1080/00397910903289271.
A. Babu, V. Babu and P. Hanumanthu, Synth. Commun., 31, 375 (2001); doi:10.1081/SCC-100000526.
R.F.W. Bader, Atoms in Molecules: A Quantum Theory, Clarendon: Oxford, U.K. (1990).
P.L. Prpelier, Atoms in Molecules: An Introduction; Pearson Education: Halow, U.K. (1999).
M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., 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. Liu, 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. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez and J.A. Pople, Gaussian, Inc., Wallingford CT, Gaussian, Inc.: Pittsburgh, PA (2004).

References

R.V. Shingalapur, K.M. Hosamani and R.S. Keri, Eur. J. Med. Chem., 44, 4244 (2009); doi:10.1016/j.ejmech.2009.05.021.

D. Zampieri, M.G. Mamolo, L. Vio, E. Banfi, G. Scialino, M. Fermeglia, M. Ferrone and S. Pricl, Bioorg. Med. Chem., 15, 7444 (2007); doi:10.1016/j.bmc.2007.07.023.

A. Puratchikody and M. Doble, Bioorg. Med. Chem., 15, 1083 (2007); doi:10.1016/j.bmc.2006.10.025.

K.C.S. Achar, K.M. Hosamani and H.R. Seetharamareddy, Eur. J. Med. Chem., 45, 2048 (2010); doi:10.1016/j.ejmech.2010.01.029.

P. Gupta, S. Hameed and R. Jain, Eur. J. Med. Chem., 39, 805 (2004); doi:10.1016/j.ejmech.2004.05.005.

F. Hadizadeh, H. Hosseinzadeh, V. Sadat Motamed-Shariaty, M. Seifi, S. Kazemi, Iran. J. Pharm. Res., 7, 29 (2008).

H.M. Refaat, Eur. J. Med. Chem., 45, 2949 (2010); doi:10.1016/j.ejmech.2010.03.022.

D. Sharma, B. Narasimhan, P. Kumar, V. Judge, R. Narang, E. De Clercq and J. Balzarini, Eur. J. Med. Chem., 44, 2347 (2009); doi:10.1016/j.ejmech.2008.08.010.

K. Bhandari, N. Srinivas, V.K. Marrapu, A. Verma, S. Srivastava and S. Gupta, Bioorg. Med. Chem. Lett., 20, 291 (2010); doi:10.1016/j.bmcl.2009.10.117.

S. Balalaie and A. Arabanian, Green Chem., 2, 274 (2000); doi:10.1039/b006201o.

S. Samai, G.C. Nandi, P. Singh and M.S. Singh, Tetrahedron, 65, 10155 (2009); doi:10.1016/j.tet.2009.10.019.

A. Hasaninejad, A. Zare, M. Shekouhy and J. Ameri Rad, J. Comb. Chem., 12, 844 (2010); doi:10.1021/cc100097m.

A. Davoodnia, M.M. Heravi, Z. Safavi-Rad and N. Tavakoli-Hoseini, Synth. Commun., 40, 2588 (2010); doi:10.1080/00397910903289271.

A. Babu, V. Babu and P. Hanumanthu, Synth. Commun., 31, 375 (2001); doi:10.1081/SCC-100000526.

R.F.W. Bader, Atoms in Molecules: A Quantum Theory, Clarendon: Oxford, U.K. (1990).

P.L. Prpelier, Atoms in Molecules: An Introduction; Pearson Education: Halow, U.K. (1999).

M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., 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. Liu, 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. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez and J.A. Pople, Gaussian, Inc., Wallingford CT, Gaussian, Inc.: Pittsburgh, PA (2004).

Issue

Vol. 26 No. 19 (2014): Vol 26 Issue 19

Theoretical Study on the Mechanism of Synthesis of 2-(p-tolyl)-1H-benzo[d]imidazole

Corresponding Author(s) : Qi-Shan Hu

Abstract

Keywords

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