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Synthesis, molecular structure, and spectral analyses of ethyl-4-[(2,4-dinitrophenyl)-hydrazonomethyl]-3,5-dimethyl-1H-pyrrole-2-carboxylate

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Abstract

Ethyl-4-[(2,4-dinitrophenyl)-hydrazonomethyl]-3,5-dimethyl-1H-pyrrole-2-carboxylate (3) has been newly synthesized by the condensation of ethyl-4-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylate and 2,4-dinitrophenylhydrazine, characterized by FT-IR, 1H NMR, UV–Vis, DART Mass and elemental analysis. The formation of compound (3) and its properties have been evaluated by quantum chemical calculations. The calculated thermodynamic parameters show that the formation reaction of (3) is exothermic and spontaneous at room temperature. The vibrational analysis indicates that (3) forms dimer in the solid state by heteronuclear double hydrogen bonding (N–H···O). Topological parameters electron density (ρ BCP), Laplacian of electron density (∇2 ρ BCP), and total electron energy density (H BCP) at bond critical points (BCP) have been analyzed using “atoms in molecules” (AIM) theory. The interaction energies of dimer formation using DFT and AIM calculations are found to be −14.6509 and −15.5308 kcal/mol, respectively. AIM ellipticity analysis confirms the presence of resonance-assisted hydrogen bonding in dimer. The global electrophilicity index (ω = 5.91 eV) shows that title molecule is a strong electrophile. The local reactivity descriptors Fukui functions (f +k , f −k ), softness (s +k , s −k ), and electrophilicity indices (ω +k , ω −k ) analyses are performed to determine the reactive sites within molecule.

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Acknowledgments

The authors are thankful to the DST New Delhi for financial supports.

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Authors and Affiliations

  1. Department of Chemistry, University of Lucknow, University Road, Lucknow, 226007, India

    R. N. Singh, Amit Kumar, R. K. Tiwari & Poonam Rawat

  2. Department of Physics, University of Lucknow, University Road, Lucknow, 226007, India

    Rajiv Manohar

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  1. R. N. Singh
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  2. Amit Kumar
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  3. R. K. Tiwari
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  4. Poonam Rawat
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Correspondence to R. N. Singh.

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Singh, R.N., Kumar, A., Tiwari, R.K. et al. Synthesis, molecular structure, and spectral analyses of ethyl-4-[(2,4-dinitrophenyl)-hydrazonomethyl]-3,5-dimethyl-1H-pyrrole-2-carboxylate. Struct Chem 24, 713–724 (2013). https://doi.org/10.1007/s11224-012-0112-1

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  • DOI: https://doi.org/10.1007/s11224-012-0112-1

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