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Vol. 30 No. 10 (2018): Vol 30 Issue 10, 2018

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Simulation of Structure, Molecular Orbitals, Electron Density and Reactivity Aspects of Rubber Vulcanization Accelerator 2-Mercaptobenzothiazole by Density Functional Theory

https://doi.org/10.14233/ajchem.2018.21419
V.K. Vijayan
Department of Chemistry, University of Calicut, Calicut-673 635, India
E. Purushothaman
Department of Chemistry, University of Calicut, Calicut-673 635, India
V. Arjunan
Department of Chemistry, Kanchi Mamuniavr Centre for Post-Graduate Studies, Puducherry-605 008, India; Rajiv Gandhi Arts & Science College, Thavalakuppam, Puducherry-605 007, India
S. Mohan
School of Sciences and Humanities, Vel Tech University, Avadi, Chennai-600 062, India

Corresponding Author(s) : V. Arjunan

varjunftir@yahoo.com; varjun.ftir@gmail.com

Asian Journal of Chemistry, Vol. 30 No. 10 (2018): Vol 30 Issue 10, 2018

Abstract

In this study, insights on the charge transfer and reactivity properties of 2-mercaptobenzothiazole are presented. The structural parameters are determined by B3LYP method. Delocalization of the lone pair electrons of S3 towards N1=C2 is possible and thereby decreases in force constant and increase in C2–S3 bond length than C2–S14. The C8–C9 bond distance increases due to the electron withdrawing nature of nitrogen. Negative electrostatic potentials reside on nitrogen whereas positive electrostatic potentials lie on hydrogen in S–H group. The LUMO–HOMO energy gap determines the charge transfer capacity and is equal to 5.1370 eV. The nS ® p*NC interaction between the sulphur (S3) lone pair and the N1=C2 antibonding orbital gives strong stabilization by 26.70 kcal mol–1. The nS ® p*NC interaction between the sulphur (S14) lone pair and the N1=C2 antibonding orbital gives stabilization by 23.77 kcal mol–1. The atoms C2, C8 and C9 are most prone to nucleophilic attack while the electrophilic attack on C2, C4 and C8 atoms. The C2, C4, C8 and C9 are more susceptible to free radical attack. The high first–order polarizability tensor reveals inductive interactions and second order polarizability tensors characterize the electron acceptor properties.

Keywords

2-Mercaptobenzothiazole DFT Natural bond orbital Hyperpolarizability Reactivity descriptors
Vijayan, V., Purushothaman, E., Arjunan, V., & Mohan, S. (2018). Simulation of Structure, Molecular Orbitals, Electron Density and Reactivity Aspects of Rubber Vulcanization Accelerator 2-Mercaptobenzothiazole by Density Functional Theory. Asian Journal of Chemistry, 30(10), 2255–2263. https://doi.org/10.14233/ajchem.2018.21419
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