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Unveiling the theoretical aspects of superelectrophilic activation in an inverse demand Diels-Alder reaction

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Abstract

The present computational study using B3LYP functional and 6-31+G(d) basis set has been accomplished to investigate the mechanism of the inverse demand Diels-Alder reaction between pyridyl imine and propene. The highly charged dicationic superelectrophilic diene with exceptionally low-lying LUMO makes the cycloaddition reaction with propene more favorable by significantly lowering the activation energy. The Wiberg bond indices are calculated in accordance with the formation and breaking processes of bonds. The synchronicity concept is also utilized to explain the global nature of the reaction. A potential outcome of this investigation is the utilization of propene as a C2 building block in the industry.

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Acknowledgements

Authors acknowledge the necessary research facilities provided by the Department of Chemistry, Indian Institute of Engineering Science and Technology, Shibpur.

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Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Engineering Science and Technology, Shibpur, Howrah, 711103, India

    Subhadip Ghosh & Prasanta K. Nandi

  2. School of Mathematical and Computational Sciences, Indian Association for the Cultivation of Science, Jadavpur, Kolkata, 700032, India

    Ria Sinha Roy

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  1. Subhadip Ghosh
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All authors contributed to the study conception, design, data collection, and analysis. All authors read and approved the final manuscript.

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Ghosh, S., Roy, R.S. & Nandi, P.K. Unveiling the theoretical aspects of superelectrophilic activation in an inverse demand Diels-Alder reaction. J Mol Model 29, 89 (2023). https://doi.org/10.1007/s00894-023-05495-7

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