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A molecular electron density theory study to understand intramolecular [3 + 2] cycloaddition reactions of azides and diazoalkanes

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Abstract

The intramolecular [3 + 2] cycloaddition (IM32CA) reactions of azides and diazoalkanes leading to fused tricyclic 1,2,3-triazolines and 1-pyrazolines have been studied at the MPWB1K/6-311G(d,p) computational level within the molecular electron density theory (MEDT). The IM32CA reactions of azides are classified as zw- type following non-concerted one-step mechanism with earlier N1-C5 bond formation implied from the bonding evolution theory (BET) study with the Gibbs free activation energies between 26.3–30.0 kcal mol−1 at 298 K in benzene while that of the diazoalkanes are classified as pmr- type with the earlier C3-C5 bond formation and Gibbs free activation energies between 24.7–29.1 kcal mol−1 at 298 K in n-pentane. The influence of substituent effects on these IM32CA reactions is studied. Azide reactions with minimal global electron density transfer (GEDT) are classified as the null electron density flux (NEDF) while that of the diazoalkanes are classified as forward electron density flux (FEDF). QTAIM analysis and ELF study allow revealing the non-covalent interactions at the TSs.

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Acknowledgements

Asmita Mondal acknowledges the support of University Grants Commission (UGC), Government of India, for Savitribai Jyotirao Phule Single Girl Child (SJSGC) Fellowship.

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Authors and Affiliations

  1. Department of Chemistry, Durgapur Government College, Durgapur, 713214, West Bengal, India

    Asmita Mondal & Nivedita Acharjee

  2. Department of Chemistry, University of Zakho, Duhok, 42001, Iraq

    Haydar A. Mohammad-Salim

  3. Department of Electronics and Communication Engineering, Dr. B. C. Roy Engineering College, Durgapur, 713206, West Bengal, India

    Mrinmoy Chakraborty

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AM performed the calculations and wrote the first draft of the manuscript. All figures, tables and schemes were then reviewed by HAMS and MC. The complete manuscript was then reviewed and finalized by NA.

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Correspondence to Nivedita Acharjee.

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11224_2023_2270_MOESM1_ESM.doc

(1) Computational Methods (2) BET study of the IM32CA reaction of azide 1 (3) BET study of the IM32CA reaction of diazoalkane 10 (4) References (5) Table with the MPWB1K/6-311G(d,p) calculated electronic energies (au) in gas phase and benzene of the stationary points involved in the IM32CA reactions of azides 1-3,12-13 and diazoalkanes 10,16-19 (6) Table with the MPWB1K/6-311G(d,p) calculated enthalpies (au), entropies (Calmol-1K-1) and Gibbs free energies (au) of the stationary points involved in the IM32CA reactions of azides 1-3,12-13  computed at 353 K and 298K in benzene and diazoalkanes 10,16-19 computed at 298 K in n-pentane (7) MPWB1K/6-311G(d,p) gas phase computed Cartesian coordinates of the stationary points involved in the IM32CA reactions of azides 1-3,12-13 (8) MPWB1K/6-311G(d,p) computed Cartesian coordinates of the stationary points involved in the IM32CA reactions of azides 1-3,12-13 in benzene at 353K (9) MPWB1K/6-311G(d,p) gas phase computed Cartesian coordinates of the stationary points involved in the IM32CA reactions of azides 1-3,12-13 in benzene at 298K (10) MPWB1K/6-311G(d,p) gas phase computed Cartesian coordinates of the stationary points involved in the IM32CA reactions of diazoalkanes 10,16-19 (11) MPWB1K/6-311G(d,p) computed Cartesian coordinates of the stationary points involved in the IM32CA reactions of diazoalkanes 10,16-19 in n-pentane at 298K. (DOC 473 KB)

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Mondal, A., Acharjee, N., Mohammad-Salim, H.A. et al. A molecular electron density theory study to understand intramolecular [3 + 2] cycloaddition reactions of azides and diazoalkanes. Struct Chem (2024). https://doi.org/10.1007/s11224-023-02270-5

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