Interaction of the 2,4-dichlorophenoxyacetic acid herbicide with soil organic matter moieties: a theoretical study
The determination of the structure of humic substances from soils and natural waters is an intriguing problem in soil science. Humic substances consist of molecules covering a broad distribution of molecular size and involving different functional groups. Taking this into account, we have chosen sma...
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| Published in | European journal of soil science Vol. 58; no. 4; pp. 889 - 899 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Oxford, UK
Oxford, UK : Blackwell Publishing Ltd
01.08.2007
Blackwell Publishing Ltd |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1351-0754 1365-2389 |
| DOI | 10.1111/j.1365-2389.2007.00928.x |
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| Abstract | The determination of the structure of humic substances from soils and natural waters is an intriguing problem in soil science. Humic substances consist of molecules covering a broad distribution of molecular size and involving different functional groups. Taking this into account, we have chosen smaller model systems with functional groups typically present in humic substances. We investigated theoretically, by quantum chemical calculations, the environmental effects on the complexes formed from the interaction of 2,4-dichlorophenoxyacetic acid and its anion with acetaldehyde, methanol, methylamine, protonated methylamine, acetic acid and water. The important case of a cation bridge mechanism, with Ca²⁺ as the bridging cation, is also included into the set of model reactions. It is found that this cation bridge belongs to one of the most stable mechanisms of fixation of organic compounds in soils. According to our calculations the hydroxyl group forms the most stable complexes with 2,4-D in a polar solvent environment. |
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| AbstractList | The determination of the structure of humic substances from soils and natural waters is an intriguing problem in soil science. Humic substances consist of molecules covering a broad distribution of molecular size and involving different functional groups. Taking this into account, we have chosen smaller model systems with functional groups typically present in humic substances. We investigated theoretically, by quantum chemical calculations, the environmental effects on the complexes formed from the interaction of 2,4‐dichlorophenoxyacetic acid and its anion with acetaldehyde, methanol, methylamine, protonated methylamine, acetic acid and water. The important case of a cation bridge mechanism, with Ca
2+
as the bridging cation, is also included into the set of model reactions. It is found that this cation bridge belongs to one of the most stable mechanisms of fixation of organic compounds in soils. According to our calculations the hydroxyl group forms the most stable complexes with 2,4‐D in a polar solvent environment. Summary The determination of the structure of humic substances from soils and natural waters is an intriguing problem in soil science. Humic substances consist of molecules covering a broad distribution of molecular size and involving different functional groups. Taking this into account, we have chosen smaller model systems with functional groups typically present in humic substances. We investigated theoretically, by quantum chemical calculations, the environmental effects on the complexes formed from the interaction of 2,4‐dichlorophenoxyacetic acid and its anion with acetaldehyde, methanol, methylamine, protonated methylamine, acetic acid and water. The important case of a cation bridge mechanism, with Ca2+ as the bridging cation, is also included into the set of model reactions. It is found that this cation bridge belongs to one of the most stable mechanisms of fixation of organic compounds in soils. According to our calculations the hydroxyl group forms the most stable complexes with 2,4‐D in a polar solvent environment. The determination of the structure of humic substances from soils and natural waters is an intriguing problem in soil science. Humic substances consist of molecules covering a broad distribution of molecular size and involving different functional groups. Taking this into account, we have chosen smaller model systems with functional groups typically present in humic substances. We investigated theoretically, by quantum chemical calculations, the environmental effects on the complexes formed from the interaction of 2,4-dichlorophenoxyacetic acid and its anion with acetaldehyde, methanol, methylamine, protonated methylamine, acetic acid and water. The important case of a cation bridge mechanism, with Ca²⁺ as the bridging cation, is also included into the set of model reactions. It is found that this cation bridge belongs to one of the most stable mechanisms of fixation of organic compounds in soils. According to our calculations the hydroxyl group forms the most stable complexes with 2,4-D in a polar solvent environment. Interaction of the 2,4-dichlorophenoxyacetic acid (2,4-D) herbicide with soil organic matter moieties was analyzed. The quantum chemical calculations were performed on two different sets of model bimolecular complexes. All calculations were performed at Density Functional Theory (DFT) level by means of the computer programs. Comparison of the energies showed that there were two sets of complexes: with one strong and one weak hydrogen bonding and with two relatively strong hydrogen bonds. In all cases, the carbonyl group of 2,4-D interacted with its partner in the dimer via hydrogen bonds. The stronger bond in each complex became even stronger under the solvent effect as compared to the gas phase. It was concluded that the most stabilizing functional group was the hydroxyl group both for neutral and deprotonated 2,4-D. |
| Author | Gerzabek, M. H. Lischka, H. Haberhauer, G. Tunega, D. Aquino, A. J. A. |
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| Snippet | The determination of the structure of humic substances from soils and natural waters is an intriguing problem in soil science. Humic substances consist of... Summary The determination of the structure of humic substances from soils and natural waters is an intriguing problem in soil science. Humic substances consist... Interaction of the 2,4-dichlorophenoxyacetic acid (2,4-D) herbicide with soil organic matter moieties was analyzed. The quantum chemical calculations were... |
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| SubjectTerms | 2,4-D acetaldehyde acetic acid acid soils anions cations environmental impact humic substances methanol methylamine molecular weight organic soils soil water |
| Title | Interaction of the 2,4-dichlorophenoxyacetic acid herbicide with soil organic matter moieties: a theoretical study |
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