Multiple studies have proven that hypochlorous acid, which is commonly used to remove contaminants from wastewater, does not effectively eliminate steroids that are present in wastewater. Instead, reactions that occur between the steroids and added chlorine yield various chlorinated organic products. It has been determined that many of these products are more bioactive than their parent compounds and pose noteworthy risks to one’s health. To demonstrate the reactivity of different types of steroids, addition and elimination reaction pathways of chlorinated enones, dienones, and trienones with water were modeled using quantum mechanical calculations. Specifically, the MN15 density functional and the Jul-cc-pDVZ basis set were employed along with the SMD aqueous continuum solvation model. Kinetic and thermodynamic properties of the mechanisms were assessed by collecting relative free energy values for each mechanism and plotting them to describe the corresponding reaction coordinate. While both types of reactions were successfully modeled, there is observable competition between the addition and elimination pathways. All calculations were performed using Gaussian 16.

Modeling the chlorination of conjugated steroids

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.