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Presence and potential significance of aromatic-ketone groups in aquatic humic substances

Organic Geochemistry

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Abstract

Aquatic humic- and fulvic-acid standards of the International Humic Substances Society were characterized, with emphasis on carbonyl-group nature and content, by carbon-13 nuclear-magnetic-resonance spectroscopy, proton nuclear-magnetic-resonance spectroscopy, and infrared spectroscopy. After comparing spectral results of underivatized humic and fulvic acids with spectral results of chemically modified derivatives, that allow improved observation of the carbonyl group, the data clearly indicated that aromatic ketone groups comprised the majority of the carbonyl-group content. About one ketone group per monocyclic aromatic ring was determined for both humic and fulvic acids. Aromatic-ketone groups were hypothesized to form by photolytic rearrangements and oxidation of phenolic ester and hydrocarbon precursors; these groups have potential significance regarding haloform formation in water, reactivity resulting from active hydrogen of the methyl and methylene adjacent to the ketone groups, and formation of hemiketal and lactol structures. Aromatic-ketone groups also may be the point of attachment between aliphatic and aromatic moieties of aquatic humic-substance structure. ?? 1987.

Additional Publication Details

Publication type:
Article
Publication Subtype:
Journal Article
Title:
Presence and potential significance of aromatic-ketone groups in aquatic humic substances
Series title:
Organic Geochemistry
Volume
11
Issue:
4
Year Published:
1987
Language:
English
Larger Work Type:
Article
Larger Work Subtype:
Journal Article
First page:
273
Last page:
280
Number of Pages:
8