Synthesis, spectroscopic analysis and theoretical study of new pyrrole-isoxazoline derivatives

Add time:08/08/2019    Source:sciencedirect.com

In the present work, we have efficiently synthesized the pyrrole-isoxazoline derivatives (4a-d) by cyclization of substituted 4-chalconylpyrrole (3a-d) with hydroxylamine hydrochloride. The reactivity of substituted 4-chalconylpyrrole (3a-d), towards nucleophiles hydroxylamine hydrochloride was evaluated on the basis of electrophilic reactivity descriptors (fk+, sk+, ωk+) and they were found to be high at unsaturated β carbon of chalconylpyrrole indicating its more proneness to nucleophilic attack and thereby favoring the formation of reported new pyrrole-isoxazoline compounds (4a-d). The structures of newly synthesized pyrrole-isoxazoline derivatives were derived from IR, 1H NMR, Mass, UV–Vis and elemental analysis. All experimental spectral data corroborate well with the calculated spectral data. The FT-IR analysis shows red shifts in vN–H and vC = O stretching due to dimer formation through intermolecular hydrogen bonding. On basis set superposition error correction, the intermolecular interaction energy for (4a-d) is found to be 10.10, 9.99, 10.18, 11.01 and 11.19 kcal/mol respectively. The calculated first hyperpolarizability (β0) values of (4a-d) molecules are in the range of 7.40–9.05 × 10−30 esu indicating their suitability for non–linear optical (NLO) applications. Experimental spectral results, theoretical data, analysis of chalcone intermediates and pyrrole–isoxazolines find usefulness in advancement of pyrrole-azole chemistry.

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