Gossypol and gossypol derivatives are natural byproducts of a variety of cotton plant species that poses interesting chemical, biological, and medicinal properties that are currently heavily researched. Supporting evidence suggest that gossypol and gossypol derivatives act on the Bcl-2 proteins that have been linked to certain cancers. Gossypol amine derivatives, specifically, are actively researched and a variety of amine derivatives have already been synthesized. However, gossypol and its derivatives are challenging compounds to work with because many of its derivatives tend to exist in various tautomeric forms. When analyzing gossypol and its derivatives it is the complex electron configuration that dictates the chemical mechanism and biological activity. The following research provides a charge density study that describes in detail the electronic configuration via Bader's topological analysis of di(methoxy)gossypol and di(propylamino) gossypol. In addition, a series of crystallographic studies of gossypol amine derivatives and di(methoxy)gossypol are also analyzed.