Structural modifications of abietic acid and a computational protocol to predict their compatibility in different...

Area of Science:

• Chemistry
• Materials Science
• Computational Chemistry

Background:

• Abietic acid, a key diterpenoid from rosin, is a valuable renewable resource.
• Its inherent polarity restricts its use in nonpolar industrial settings.
• Tailoring abietic acid derivatives is crucial for expanding their applications.

Purpose of the Study:

• To develop and validate a computational protocol for predicting the impact of structural changes on abietic acid's polarity.
• To guide the rational design of abietic acid derivatives with tunable properties.
• To assess the compatibility of abietic acid derivatives in various environments.

Main Methods:

• Utilized molecular mechanics conformational searches and DFT optimizations.
• Calculated population-weighted dipole moments and Gibbs free energies of solvation.
• Compared computational predictions with experimental HPLC-DAD and TLC data.

Main Results:

• The computational protocol accurately predicted trends in polarity and compatibility.
• Subtle conformational effects, like pseudo-amphiphilicity in dodecyl abietate, were captured.
• Good agreement was observed between calculated descriptors and experimental retention times/Rf values.

Conclusions:

• The developed computational framework is a reliable tool for predicting molecular polarity.
• This method enables the rational design of abietic acid derivatives with specific polarity characteristics.
• The study facilitates the development of novel abietic acid-based materials for diverse industrial needs.