R. N. Singh, Amit Kumar, R. K. Tiwari
Mar 13, 2013
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Journal
Journal of Molecular Structure
Abstract
Abstract The carboxaldehydes of pyrrole form important class of precursors for synthesis of acid hydrazide-hydrazones and their derivatives which show the various applications. A novel hydrazide-hydrazone of pyrrole: Ethyl-4-[(benzoyl)-hydrazonomethyl]-3,5-dimethyl-1 H -pyrrole-2-carboxylate ( 3 ) has been synthesized by condensation of ethyl-4-formyl-3,5-dimetyl-1 H -pyrrole-2-carboxylate and benzohydrazide. The product was characterized by spectroscopy methods (FT-IR, 1 H NMR, UV–Vis and DART Mass) and quantum chemical calculations. The calculated thermodynamic parameters show that the formation of ( 3 ) is exothermic and spontaneous at room temperature. The local electronic descriptors analysis and molecular electrostatic potential surface were used to predict the sites and nature of interactions which indicate the dimer formation through multiple interaction through N H⋯O and C–H⋯O. The vibrational analysis shows red shifts in v N H and v C O as result of dimer formation. Topological and energetic parameters generated by AIM show the nature of interactions in dimer. The interaction energies of dimer formation using DFT and AIM calculations are found to be 14.19 and 15.19 kcal/mol respectively. Ellipticity analysis confirms the presence of resonance assisted heteronuclear H-bonding in dimer.