Temperature-dependent oxidation of BSCAPE molecule in methanol medium

Area of Science:

• Computational Chemistry
• Physical Chemistry
• Biochemistry

Background:

• 2-Phenylethyl (2E)-3-(1-benzenesulfonyl-4,5-dihydroxyphenyl) acrylate (BSCAPE) is a phenolic acid with known bioactivities.
• Understanding its solvation and oxidation is crucial for elucidating its metabolic pathways.

Purpose of the Study:

• To investigate the temperature-dependent solvation free energy and oxidation free energy of BSCAPE in methanol.
• To explore the influence of methanol as a solvent on BSCAPE's properties.
• To determine the spontaneity of solvation and coordination processes.

Main Methods:

• Employed explicit, implicit, and discrete-continuum solvation models.
• Utilized the M06-2X/6-31++G(d,p)//B3LYP/6-31G(d) computational method with basis set superposition error correction.
• Calculated free energy of coordination, solvation, and ionization potential.

Main Results:

• Solvation and coordination free energies were found to be distinct and increased with temperature.
• The solvation process was non-spontaneous, while coordination showed temperature-dependent spontaneity.
• Ionization potential decreased with temperature in both gas and solution phases.
• Higher temperatures and methanol favor BSCAPE oxidation.

Conclusions:

• The increase in temperature and the presence of methanol favor the oxidation of BSCAPE.
• These findings suggest a favorable environment for BSCAPE metabolism at elevated temperatures in methanol.