pH effects on sorption of nonionic compounds to soils: Possible involvement of π-π charge-transfer interactions for PAHs and other strong electron donor aromatic compounds

Dongqiang Zhu, Joseph J. Pignatello, Seunghun Hyun, Linda L. Lee

Research output: Chapter in Book/Report/Conference proceedingConference contribution

1 Citation (Scopus)

Abstract

Sorption of pi-donors, pentamethylbenzene (PMB), naphthalene (NAPH), and phenanthrene (PHEN), to soils increases with decreasing pH, whereas a reversed trend is observed for 2-nonanol and 2-nonanone, which are non pi-donors but capable of H-bonding. No significant pH effect is observed for non pi-donor, hydrophobic compounds: trans-1,2-dichlorocyclohexane, hexachloro-1,3-butadiene, 1,2,4-trichloro-benzene and 2,2′,5,5′-tetrachlorobiphenyl. These results cannot be explained by pH-dependent H-bonding or by hydrophobicity of soil organic matter (SOM). Instead, pi-pi charge-transfer interactions are proposed between donors and SOM pi-accepting sites, including N-heteroaromatic cations and aromatic rings with multiple carboxyl groups. The pi-pi interaction between donors, PMB, NAPH, and PHEN and model SOM acceptors, 1,3,5-benzenetricarboxylic acid (BTA) and 1,4,5,8-naphthalene-tetracarboxylic acid, was verified by upfield 1H NMR chemical shifts in methanol and methanol-water. The donor affinity of BTA for PMB was reduced by deprotonation of BTA.

Original languageEnglish
Title of host publicationACS Division of Environmental Chemistry, Preprints
Volume43
Edition2
Publication statusPublished - 2003
Externally publishedYes

Fingerprint

pH effects
Aromatic compounds
Polycyclic aromatic hydrocarbons
Sorption
Charge transfer
Naphthalene
Biological materials
Soils
Acids
Electrons
Methanol
Deprotonation
Chemical shift
Hydrophobicity
Benzene
Butadiene
Cations
Positive ions
Nuclear magnetic resonance
Water

ASJC Scopus subject areas

  • Chemical Engineering(all)

Cite this

pH effects on sorption of nonionic compounds to soils : Possible involvement of π-π charge-transfer interactions for PAHs and other strong electron donor aromatic compounds. / Zhu, Dongqiang; Pignatello, Joseph J.; Hyun, Seunghun; Lee, Linda L.

ACS Division of Environmental Chemistry, Preprints. Vol. 43 2. ed. 2003.

Research output: Chapter in Book/Report/Conference proceedingConference contribution

Zhu, Dongqiang ; Pignatello, Joseph J. ; Hyun, Seunghun ; Lee, Linda L. / pH effects on sorption of nonionic compounds to soils : Possible involvement of π-π charge-transfer interactions for PAHs and other strong electron donor aromatic compounds. ACS Division of Environmental Chemistry, Preprints. Vol. 43 2. ed. 2003.
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abstract = "Sorption of pi-donors, pentamethylbenzene (PMB), naphthalene (NAPH), and phenanthrene (PHEN), to soils increases with decreasing pH, whereas a reversed trend is observed for 2-nonanol and 2-nonanone, which are non pi-donors but capable of H-bonding. No significant pH effect is observed for non pi-donor, hydrophobic compounds: trans-1,2-dichlorocyclohexane, hexachloro-1,3-butadiene, 1,2,4-trichloro-benzene and 2,2′,5,5′-tetrachlorobiphenyl. These results cannot be explained by pH-dependent H-bonding or by hydrophobicity of soil organic matter (SOM). Instead, pi-pi charge-transfer interactions are proposed between donors and SOM pi-accepting sites, including N-heteroaromatic cations and aromatic rings with multiple carboxyl groups. The pi-pi interaction between donors, PMB, NAPH, and PHEN and model SOM acceptors, 1,3,5-benzenetricarboxylic acid (BTA) and 1,4,5,8-naphthalene-tetracarboxylic acid, was verified by upfield 1H NMR chemical shifts in methanol and methanol-water. The donor affinity of BTA for PMB was reduced by deprotonation of BTA.",
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