“Benzimidazoles and their derivatives, which have good biological activities and reactive activities, are very useful intermediates for the development of molecules on pharmaceutical or biological interest [21-24]. The proton transfer behavior of 2-substituted benzimidazole compounds has been an interesting topic for years [25-30]. Especially, the hydrogen bond of these compounds is close to the length of the low-barrier hydrogen bond (LBHB) [31,32]. Which will help to study the interrelation between the barrier and the p-electron delocalization.”
References
Peng, H., Huang, P., Yi, P., Xu, F., & Sun, L. (2018). Theoretical studies of π-electron delocalization and localization on intramolecular proton transfer in the ground state. Journal of Molecular Structure, 1154, 590-595.https://doi.org/10.1016/j.molstruc.2017.10.079
Author’s references
[21] Y. Bansal, O. Silakari, The therapeutic journey of benzimidazoles: a review, Biorg. Med. Chem. 20 (2012) 6208-6236.
[22] H. Wang, Y. Wang, C. Peng, J. Zhang, Q. Zhu, Direct intramolecular C-H ami- nation reaction cocatalyzed by copper(II) and iron(III) as part of an efficient route for the synthesis of pyrido 1,2-a benzimidazoles from N-Aryl-2-aminopyridines, J. Am. Chem. Soc. 132 (2010) 13217-13219.
[23] J. Plutnar, M. Hromadova, N. Fanelli, S. Ramesova, Z. Havlas, L. Pospisil, Elec- tron transfer mechanism of substituted benzimidazoles: dimer switching, oscillations, and search for singlet fission properties, J. Phys. Chem. C 121 (2017) 9963-9969.
[24] S. Rajasekhar, B. Maiti, M.M. Balamurali, K. Chanda, Synthesis and medicinal applications of benzimidazoles: an overview, Curr. Org. Synth. 14 (2017) 40-60.
[25] X.-F. Han, M.-M. Chen, Z.-M. Zhou, Synthesis of several new 2-substituted benzimidazoles, J. Chem. Res. (2015) 407-409.
[26] P. Ghosh, R. Subba, MgCl2 center dot 6H(2)O catalyzed highly efficient synthesis of 2-substituted-1H-benzimidazoles, Tetrahedron Lett. 56 (2015) 2691-2694.
[27] V. Kumar, D.G. Khandare, A. Chatterjee, M. Banerjee, DBSA mediated chemoselective synthesis of 2-substituted benzimidazoles in aqueous media, Tetrahedron Lett. 54 (2013) 5505-5509.
[28] F.K. Behbahani, P. Ziaei, One-pot synthesis of 2-substituted benzimidazoles catalyzed by anhydrous FePO4, Chem. Heterocycl. Compd. 48 (2012) 1011-1017.
[29] H. Shi, B. Xu, H.-J. Zhu, Electrochemical and theoretical studies of 1-Alkyl-2-substituted benzimidazoles as corrosion inhibitors for carbon steel surface in HCl medium, Chin. J. Struct. Chem. 35 (2016) 1829-1839.
[30] J. Kovvuri, B. Nagaraju, A. Kamal, A.K. Srivastava, An efficient synthesis of 2-substituted benzimidazoles via photocatalytic condensation of o-phenyl-enediamines and aldehydes, ACS Comb. Sci. 18 (2016) 644-650.
[31] P.A. Frey, S.A. Whitt, J.B. Tobin, A low-barrier hydrogen-bond in the catalytic triad of serine proteases, Science 264 (1994) 1927-1930.
[32] W.W. Cleland, M.M. Kreevoy, Low-barrier hydrogen-bonds and enzymatic catalysis, Science 264 (1994) 1887-1890.