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Extraction and production of viscous petroleum or bitumen in Alberta, Canada has rapidly developed in the last 30 years, and in 2022 the average daily production was nearly 4 million barrels/day. As a result of the increased global demand of crude oil and technical improvements in the extraction process of surface mining and in situ technologies, this daily output of crude oil is expected to increase further. Surface mining operations are required to invest and implement long-term reclamation strategies in order to properly reduce/manage the large volumes of oil sands process-affected water (OSPW) and tailings and convert the surrounding mining area into an environment similar to its initial state. Commissioned in late 2012 within Syncrude’s Mildred Lake mining site is Base Mine Lake (BML), the first full-scale demonstration of Water Capped Tailings Technology. This aquatic reclamation environment serves as the first of many oil sands pit lakes proposed in the surrounding region, therefore, it is crucial that a comprehensive assembly of scientific pursuits are incorporated into the monitoring and research programs of BML. The presence of petroleum-associated organic compounds, such as Hydrocarbons and Naphthenic acid Fraction compounds (NAFC), remains a top priority for evaluating how BML meets surface water guidelines, but also plays a larger role in the scientific understanding of how biogeochemical and physical processes can impact the environmental fate and transport of these organic compounds in future oil sand pit lakes. This master’s dissertation is focused on the use of ultra-high resolution mass spectrometry to determine the molecular profile of NAFCs extracted from BML in 2019. In this thesis, electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry (ESI-FT ICR MS) was used to investigate: i) how particular experimental variables impact the qualitative measurements of oil sand NAFCs, and ii) the spatial variability of NAFCs within the BML water cap and FFT with the aim of providing novel insights to key biogeochemical processes and potential transport mechanisms for continued NAFC inputs in the water column. / Thesis / Master of Science (MSc)

This thesis discusses two major projects. The first project focuses on understanding the effect of chirality on intrinsic acidity of oligopeptides. Gas-phase acidity (ΔacidG) and related thermochemical parameters (ΔacidH, and ΔacidS), of model N- and C-terminal cysteine polyalanine peptides in which one L-alanine was substituted by a D-alanine viz. CAADA and AADAC, were measured by the extended Cooks kinetic method. Gas-phase acidities of CAADA and AADAC were measured to be about 318 kcal/mol and 322 kcal/mol, respectively. These values are different from the gas-phase acidities of the all L-amino acid containing analogues of the above peptides, but suggest that D-alanine containing peptides show the same trend as their all L-amino acid analogues with the N-terminal cysteine peptide being more acidic than the C-terminal cysteine peptide. However, the difference in the acidities of CAADA and AADAC is about 4 kcal/mol which is about half of the difference between their all L-amino acid analogues. These results also suggest that, presumably, a single L-alanine to D-alanine substitution has a moderate effect on the conformation of the respective peptides. The aim of the second project is to understand how acidic amino acids influence peptide fragmentation during tandem mass spectrometric analysis. A series of model N- and C- terminal glutamic acid polyalanine and polyglycine (EAn, AnE (n=2,3); EGn (n=2,3), GnE (n=2-4)) and cysteine polyalanine (CAn, AnC (n=4-6)) peptides were studied. Primarily, EAn and EGn peptides formed bn ions. In contrast, while EOn peptides formed all yn ions, EAn peptides formed fewer yn ions. Similarly, AnE and GnE peptides also formed bn ions. No major differences were observed in yn ion formation. For both sets of peptides, water loss seemed to trend with the position of glutamic acid. CAn and AnC peptides also formed bn ions, just like their glutamic acid counterparts. However, yn ions were observed only for AnC peptides. For all sets of peptides, ions related to bn and yn ions were also observed.

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