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Table 1 Overview of possible changes to the environment of an atom. Changes are detected by comparing atoms that are mapped to each other. In each example case, the changes in the environment of the blue atom are assessed. This is done by either comparing the two blue atoms directly (for radicals, charges and stereo), or by comparing the surroundings (bond changes)

From: Automated reaction database and reaction network analysis: extraction of reaction templates using cheminformatics

Changes in environment

Example

Description

Losing/gaining neighbors

Comparing neighbors of ‘A’ and their bonds to ‘A’ to those of ‘A’s mapped counterpart. A match is found if all neighboring element names are equal and all neighboring mapping indices are equal

Changing bond orders

Comparing the order of ‘A’s bonds to those of ‘A’s mapped counterpart. Marked if the bond order between ‘A’ and a neighbor has changed

Losing/gaining radicals

Comparing single electron count of ‘A’ to its mapped counterpart

Losing/gaining charge

Comparing charge on ‘A’ to that on ‘A’s mapped counterpart

Changing stereo configuration

Comparing E/Z or R/S configuration of ‘A’ to that of its mapped counterparts