Energy profile analysis, spectroscopic investigations (FT–IR, FT–Raman and FT–NMR), electronic properties, structure‒activity aspects and DFT studies of (1,3‒benzodioxol‒5‒yl)acetic acid

Abstract

Abstract The interaction of electromagnetic interaction by comprehensive theoretical and experimental FT‒IR, FT‒Raman and FT‒NMR spectroscopic studies of (1,3‒benzodioxol‒5‒yl)acetic acid (BDA) have been carried out. DFT/B3LYP method with 6‒311++G** and cc‒pVTZ basis sets have been used to determine the molecular properties of BDA. Five different conformers I, II, III, IV and V of BDA has been determined by potential energy profile. The most stable BDA molecule adopts a non‒planar (puckered) conformation I. The total energy, heat capacity, entropy, vibrational energy and zero point energy calculated by B3LYP/cc‒pVTZ basis sets are 106.34 kcal mol‒1, 40.22 kcal mol‒1 K‒1, 103.44 kcal mol‒1, 104.56 kcal mol‒1 and 99.72 kcal mol‒1, respectively. The total electron density of the BDA molecule spread between + 5.53e ×10‒2 and ‒5.531e ×10‒2. The electrostatic potential are lie in the range ± 1.123e ×10‒2. In BDA molecule n(O12) → π* C11‒O13 interaction is strongly stablised by 42.5 kcal mol‒1. The carbon atoms C3 and C4 are highly deshielded due to –I effect of highly electronegative oxygen. The symmetrical O‒C‒O vibration is blue shifted by 20 and 24 cm‒1 in FT‒IR and FT‒Raman spectra, respectively, when compared to methylenedioxy benzene. The reactivity order for the electrophilic attack is C9 > C10 > C11 while the reactivity order for the nucleophilic attack is C10 > C9 > C3.