Donor–acceptor dichotomy in novel Schiff bases: comprehensive spectroscopic and DFT investigation of intramolecular hydrogen bonding and charge-transfer properties

Key Points

• To explore the donor-acceptor dichotomy and hydrogen bonding in Schiff bases using spectroscopic and computational methods.
• Conducted spectroscopic analyses including UV-Vis and NMR.
• Utilized Kamlet–Taft parameters to assess solvatochromic effects.
• Applied Natural Bond Orbital (NBO) and Atoms in Molecules (AIM) methods for computational insights.
• Employed Density Functional Theory (DFT) to calculate HOMO-LUMO gaps.
• Identified significant intramolecular O–H⋯N hydrogen bonding interactions.
• Characterized solvatochromic charge-transfer bands in the compounds.
• Calculated varying HOMO-LUMO gaps indicative of different electronic properties.

Abstract