ORCID

https://orcid.org/0009-0009-7741-6542

Date of Award

2025

Document Type

Thesis

Degree Name

MS in Chemistry

Department

Chemistry

First Advisor

Anne VΓ‘quez

Second Advisor

Enju Wang

Third Advisor

Joseph Serafin

Abstract

The oil sand regions in Alberta, Canada have proven to be costly to the environment despite its economic benefits. The toxins produced during oil processing are sent to tailing ponds to be recycled, though often leaking into nearby waterways and soil. Naphthenic acids, NAs, are one of the most common toxins produced and have shown to be toxic to aquatic life, animals, and humans. As there is dissolved organic matter in tailing ponds and surrounding environments, tailing ponds often lead to NAs coming in contact with organic material. Humic acid, HA, is a major soil component that has been suspected to bind with NAs though the exact mechanisms are unknown. Raman spectroscopy experiments and Gaussian electronic structure calculations were performed to investigate the suspected non- covalent interactions gathered by past fluorescence quenching studies. In Raman studies, a solution of HA was titrated with NA model compounds of different polarities to investigate possible interactions between HA and NAs. As HA is complex, three chemical groups in HA that are likely to be involved in binding were chosen for computational studies. The basis set DFT/πœ”B97X-D/6-311++G(d,p) was used to account for polarization and diffusion while using specific equations for different atoms. We found evidence of weak interactions between HA and the model NAs. Raman results showed intensity changes with increased titrations of NA into HA. Electronic structure modeling results indicated the possibility of hydrogen bonding and πœ‹ βˆ’ πœ‹ stacking based on the obtained energy, distance, and angle values.

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