Automated simultaneous assignment of bond orders and formal charges

Area of Science:

• Computational Chemistry
• Cheminformatics

Background:

• Accurate assignment of bond orders and formal charges is crucial for cheminformatics applications.
• Automating this process with minimal input is a significant challenge.

Purpose of the Study:

• To develop and evaluate a method for automatically assigning bond orders and formal charges from molecular structure.
• To compare the performance of different optimization algorithms for this task.

Main Methods:

• Utilized a graph theoretical approach to represent electron positions.
• Scored electron assignments using lookup tables of atomic and bond dissociation energies from quantum chemical calculations.
• Tested local optimization, A* pathfinding, and FPT optimization methods.

Main Results:

• The developed method accurately assigns bond orders and formal charges across diverse molecular databases.
• The FPT optimization algorithm showed superior performance in terms of speed and accuracy.
• The method relies solely on atom types and connectivity for input.

Conclusions:

• The proposed graph theoretical method effectively automates the assignment of fundamental chemical descriptors.
• The FPT algorithm is the recommended approach for optimizing electron position assignments in this context.