For the initial
tests, cis-pinonic acid and cis-pinonaldehyde
were each dissolved in 10 M H2SO4, resulting
in an effective pH of −1.08, with dissolution in water serving
as a control. The pH values cited in this work correspond to the negative
logarithm of the molality of H+, which is estimated using
the extended aerosol inorganic model I (E-AIM).44 (link)−46 Once it was
confirmed that there were significant changes in the composition and
optical properties of the acidified sample, additional experiments
were performed at varying acidities. In all cases, an aliquot of the
stock cis-pinonic acid or cis-pinonaldehyde
with a concentration of 2000 μg/mL was added to a 4 mL aqueous
solution containing H2SO4 (Table S1), resulting in a mass concentration of 35–70
μg/mL. To conduct NMR analysis, it was necessary to scale up
the reaction to generate sufficient material for purification and
subsequent analysis, as explained in detail in the SI. All samples
were neutralized with sodium carbonate before disposal.
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