A novel dihydrocoumarin under experimental and theoretical characterization

Area of Science:

• Organic Chemistry
• Crystallography
• Computational Chemistry

Background:

• Coumarins are versatile compounds with applications in medicine, including cancer and inflammation treatments.
• Dihydrocoumarin derivatives are of significant interest in organic chemistry due to their structural flexibility.

Purpose of the Study:

• To perform a comprehensive structural and spectroscopic characterization of the synthesized dihydrocoumarin compound 4-(4-methoxyphenyl)-3,4-dihydro-chromen-2-one (C16H14O3).
• To investigate the molecular interactions, electronic properties, and stability of the compound using theoretical calculations.

Main Methods:

• Synthesis and crystallization of 4-(4-methoxyphenyl)-3,4-dihydro-chromen-2-one.
• X-ray crystallography for structural determination.
• Spectroscopic analyses (FTIR, NMR - implied) for functional group identification.
• Density Functional Theory (DFT) and Car-Parrinello molecular dynamics for electronic structure and geometry optimization.
• Natural Bond Orbital (NBO) analysis for molecular orbital characterization.

Main Results:

• The crystallographic structure confirmed the presence of aromatic carbons, hydrogen atoms, carbonyl, and methoxy groups.
• Non-classical C-H···O intermolecular interactions were identified as key drivers of crystal packing.
• Spectroscopic and vibrational frequency analyses confirmed the functional groups and identified main absorbent groups.
• DFT calculations revealed sites for nucleophilic/electrophilic attack and molecular electrostatic potential.
• NBO analysis identified π-bonding and π* antibonding orbitals.

Conclusions:

• The synthesized dihydrocoumarin derivative exhibits high kinetic stability and low chemical reactivity, indicated by the HOMO-LUMO gap.
• The study provides a detailed structural and electronic characterization of the compound, relevant for medicinal chemistry and materials science.
• Intermolecular interactions play a crucial role in the solid-state arrangement of this dihydrocoumarin derivative.