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DFT investigation on the intramolecular and intermolecular proton transfer processes in 2-aminobenzothiazole (ABT) in the gas phase and in different solvents

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Abstract

DFT at the B3LYP/6-311++G(d,p) level of theory was performed to geometrically, thermodynamically, and kinetically investigate the tautomerism process of 2-aminobenzothiazole (ABT) with n water molecules (n = 1–3) and without water in the gas phase and in different solvents with a gradual increase in their dielectric constants. The geometries of the envisaged tautomers were optimized in the gas phase and in solution with the polarized continuum model (PCM). Equilibrium and rate constants for the forward and reverse intra-/intermolecular isolated and water-assisted tautomerism reactions were also calculated. The results suggest that the activation energy of the transition state of direct proton transfer in the isolated reaction is very high and that the rate constant is very slow (~ 10−24 s), reflecting that the reaction is thermodynamically unfavored, whereas the barrier differences between the transition states of the tautomers decrease gradually as the number of water molecules increases from one to three. Moreover, the rate constants of the proposed reactions are ~ 1023–1025 faster than those of the isolated reaction, and the water-assisted tautomerism paths can be performed quickly, especially with the assistance of two molecules of water.

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Acknowledgments

This work was supported by the Deanship of Scientific Research (DSR), King Abdulaziz University, Jeddah, under grant No. (130 - 217 - D1440). The authors, therefore, gratefully acknowledge the DSR technical and financial support. The authors acknowledge King Abdulaziz University’s High-Performance Computing Centre (Aziz Supercomputer) (http://hpc.kau.edu.sa) for supporting the computation for the work described in this paper.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O Box 42805, Jeddah, 21589, Saudi Arabia

    Nuha Wazzan, Roqaya Al-Barakati, Ohoud Al-Qurashi & Lateefa Al-Khateeb

  2. Department of Chemistry, Faculty of Science, Al Azhar University-Gaza, P.O Box 1277, Gaza, City, Palestine

    Zaki Safi

  3. Chemistry Department, Faculty of Science, University of Jeddah, P.O Box 42805, Jeddah, 21589, Saudi Arabia

    Ohoud Al-Qurashi

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  1. Nuha Wazzan
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Correspondence to Nuha Wazzan.

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Wazzan, N., Safi, Z., Al-Barakati, R. et al. DFT investigation on the intramolecular and intermolecular proton transfer processes in 2-aminobenzothiazole (ABT) in the gas phase and in different solvents. Struct Chem 31, 243–252 (2020). https://doi.org/10.1007/s11224-019-01395-w

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