Aqueous-phase photooxygenation of enes, amines, sulfides and polycyclic aromatics by singlet (a1Δg) oxygen: prediction of rate constants using orbital energies, substituent factors and quantitative structure–property relationships
Tom M. Nolte A D and Willie J. G. M. Peijnenburg B C
+ Author Affiliations
- Author Affiliations
A Department of Environmental Science, Institute for Water and Wetland Research, Radboud University Nijmegen, PO Box 9010, 6500 GL Nijmegen, The Netherlands.
B National Institute of Public Health and the Environment, PO Box 1, 3720 BA Bilthoven, The Netherlands.
C Institute of Environmental Sciences (CML), Leiden University, PO Box 9518, 2300 RA, Leiden, The Netherlands.
D Corresponding author. Email: tom.m.nolte@gmail.com
Environmental Chemistry 14(7) 442-450 https://doi.org/10.1071/EN17155
Submitted: 19 July 2017 Accepted: 10 October 2017 Published: 31 January 2018
Environmental context. To aid the transition to sustainable chemistry there is a need to improve the degradability of chemicals and limit the use of organic solvents. Singlet oxygen, 1O2, is involved in organic synthesis and photochemical degradation; however, information on its aqueous-phase reactivity is limited. We developed cheminformatics models for photooxidation rate constants that will enable accurate assessment of aquatic photochemistry without experimentation.
Abstract. To aid the transition to sustainable and green chemistry there is a general need to improve the degradability of chemicals and limit the use of organic solvents. In this study we developed quantitative structure–property relationships (QSPRs) for aqueous-phase photochemical reactions by singlet (a1Δg) oxygen. The bimolecular singlet oxygen reaction rate constant can be reliably estimated (R2 = 0.73 for naphtalenes and anthracenes, R2 = 0.86 for enes and R2 = 0.88 for aromatic amines) using the energy of the highest occupied molecular orbital (EHOMO). Additional molecular descriptors were used to characterise electronic and steric factors influencing the rate constant for aromatic enes (R2 = 0.74), sulfides and thiols (R2 = 0.72) and aliphatic amines. Mechanistic principles (frontier molecular orbital, perturbation and transition state theories) were applied to interpret the QSPRs developed and to corroborate findings in the literature. Depending on resonance, the speciation state (through protonation and deprotonation) can heavily influence the oxidation rate constant, which was accurately predicted. The QSPRs can be applied in synthetic photochemistry and for estimating chemical fate from photolysis or advanced water treatment.
Additional keywords: degradation, organic photochemistry.
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