Quantitative structure–property relationships on photodegradation of PCDD/Fs in cuticular waxes of laurel cherry ( Prunus laurocerasus)

• Published in: The Science of the total environment Vol. 269; no. 1; pp. 163 - 170
• Main Authors: Chen, Jingwen, Quan, Xie, Yang, Fenglin, Peijnenburg, Willie J.G.M
• Format: Journal Article
• Language: English
• Published: Shannon Elsevier B.V 26.03.2001; Elsevier Science
• Subjects: Animal, plant and microbial ecology; Applied ecology; Benzofurans - analysis; Benzofurans - pharmacokinetics; Biological and medical sciences; Ecotoxicology, biological effects of pollution; Effects of pollution and side effects of pesticides on plants and fungi; Fundamental and applied biological sciences. Psychology; Light; Models, Theoretical; PCDD/Fs; Photodegradation; Plants; PLS; Polychlorinated Dibenzodioxins - analogs & derivatives; Polychlorinated Dibenzodioxins - analysis; Polychlorinated Dibenzodioxins - pharmacokinetics; Prunus laurocerasus; QSPR; Quantum chemical descriptors; Soil Pollutants - analysis; Soil Pollutants - pharmacokinetics; Structure-Activity Relationship; Photodegradation; QSPR; Quantum chemical descriptors; PCDD/Fs; PLS; Light effect; Prunus laurocerasus; Chlorination; Rosaceae; Cuticle; Plant leaf; Organochlorine compounds; Dicotyledones; Angiospermae; Spermatophyta; Models; Kinetics; Partial least squares; Plant wax; Photochemical degradation
• ISSN: 0048-9697; 1879-1026
• DOI: 10.1016/S0048-9697(00)00827-5

By the use of the partial least squares (PLS) method and 13 fundamental quantum chemical descriptors computed by PM3 Hamiltonian, a QSPR model was developed for first order rate constants of photodegradation of 10 PCDD/Fs dissolved in cuticular wax from laurel cherry ( Prunus laurocerasus) leaves and exposed to sunlight. The QSPR showed that photodegradation rates increase with the degree of chlorination of the homologues. PCDD/Fs with large values of Q Cl (the largest positive atomic charge on a chlorine atom in a molecule), Q O − (the most negative atomic charge on the oxygen atoms in a molecule), and μ (dipole moment) tend to photodegrade fastest. PCDD/Fs with large values of E lumo (the energy of the lowest unoccupied molecular orbital), E homo (the energy of the highest occupied molecular orbital), and E lumo− E homo tend to have the lowest photodegradation rates.