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Synthesis of zwitterionic compounds for aquatic toxicity testing for QSAR correlation studies. / Joanna Davies

Swansea University Author: Joanna Davies

Abstract

22 zwitterionic compounds (10 short-chain surfactants; 12 non-surfactants) were synthesised obeying the general formula R-N+(CH3)2(CH2)nSO3', where n = 2 to 4, by reacting the corresponding N, N-dimethylamines with either sodium-2-chloroethane sulfonate (n = 2), 1, 3- propanesulfonate (n = 3) o...

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Published: 2003
Institution: Swansea University
Degree level: Doctoral
Degree name: Ph.D
URI: https://cronfa.swan.ac.uk/Record/cronfa42651
first_indexed 2018-08-02T18:55:13Z
last_indexed 2018-08-03T10:10:43Z
id cronfa42651
recordtype RisThesis
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spelling 2018-08-02T16:24:29.9929983 v2 42651 2018-08-02 Synthesis of zwitterionic compounds for aquatic toxicity testing for QSAR correlation studies. 85bcbc801ad156532cd34cbc1744b8c5 NULL Joanna Davies Joanna Davies true true 2018-08-02 22 zwitterionic compounds (10 short-chain surfactants; 12 non-surfactants) were synthesised obeying the general formula R-N+(CH3)2(CH2)nSO3', where n = 2 to 4, by reacting the corresponding N, N-dimethylamines with either sodium-2-chloroethane sulfonate (n = 2), 1, 3- propanesulfonate (n = 3) or 1,4-butanesulfonate (n = 4). The R group varied from a C6 to C12 alkyl chain, to a phenylalkyl unit bearing a Cl to C4 chain and finally to a phenylpropyl unit with a C4 to C6 para-substituted alkyl group. Octanol/water partition coefficients of the 22 sulfobetaines were determined by a conventional stir-flask procedure. The amount of solute in both the octanol and water layer was quantified using a reverse-phase HPLC technique. A UV detection mechanism was employed for those sulfobetaines that possessed a suitable chromophore for UV detection and an electrospray ionisation mode of detection was used for the analysis of those sulfobetaines that lacked a chromophore suitable for UV detection. Acute aquatic toxicity to the aquatic invertebrate, Daphnia magna Straus, was reported as log (l/EC50). The EC50 values were determined experimentally using a standard Acute Immobilisation Test recommended by the OECD Guideline 202 and the internal Unilever document, Ecotoxicology SOP 019 11. A log P-based QS AR was then derived which was found to be analogous to the standard polar narcosis equation, suggesting that zwitterionic sulfobetaines act as polar narcotics. Experimental log P determined by the stir-flask procedure and the rules of Rekker and Roberts for the calculation of log P for quaternary ammonium compounds of the cationic type, were then used in the derivation of key fragment values and interaction factors for use in log P calculations of sulfobetaines using the Leo and Hansch approach. Furthermore, log P predictions provided by KowWin, a computerised program developed by the Syracause Research Cooperation, were suitably amended to take into consideration our experimental results. Finally, an investigation into the suitability of the phospholipophilicity parameter, log k'lAM, for defining aquatic toxicity was performed and the efficacy of using this parameter and log P to predict aquatic toxicity was compared. In addition, other chromatographic methods for estimating log P were investigated. These include the indirect reverse-phase HPLC method, the direct reverse-phase HPLC method and Counter Current Chromatography. E-Thesis Chemical engineering.;Toxicology. 31 12 2003 2003-12-31 COLLEGE NANME Chemistry COLLEGE CODE Swansea University Doctoral Ph.D 2018-08-02T16:24:29.9929983 2018-08-02T16:24:29.9929983 Faculty of Science and Engineering School of Engineering and Applied Sciences - Chemistry Joanna Davies NULL 1 0042651-02082018162511.pdf 10805427.pdf 2018-08-02T16:25:11.2230000 Output 10473264 application/pdf E-Thesis true 2018-08-02T16:25:11.2230000 false
title Synthesis of zwitterionic compounds for aquatic toxicity testing for QSAR correlation studies.
spellingShingle Synthesis of zwitterionic compounds for aquatic toxicity testing for QSAR correlation studies.
Joanna Davies
title_short Synthesis of zwitterionic compounds for aquatic toxicity testing for QSAR correlation studies.
title_full Synthesis of zwitterionic compounds for aquatic toxicity testing for QSAR correlation studies.
title_fullStr Synthesis of zwitterionic compounds for aquatic toxicity testing for QSAR correlation studies.
title_full_unstemmed Synthesis of zwitterionic compounds for aquatic toxicity testing for QSAR correlation studies.
title_sort Synthesis of zwitterionic compounds for aquatic toxicity testing for QSAR correlation studies.
author_id_str_mv 85bcbc801ad156532cd34cbc1744b8c5
author_id_fullname_str_mv 85bcbc801ad156532cd34cbc1744b8c5_***_Joanna Davies
author Joanna Davies
author2 Joanna Davies
format E-Thesis
publishDate 2003
institution Swansea University
college_str Faculty of Science and Engineering
hierarchytype
hierarchy_top_id facultyofscienceandengineering
hierarchy_top_title Faculty of Science and Engineering
hierarchy_parent_id facultyofscienceandengineering
hierarchy_parent_title Faculty of Science and Engineering
department_str School of Engineering and Applied Sciences - Chemistry{{{_:::_}}}Faculty of Science and Engineering{{{_:::_}}}School of Engineering and Applied Sciences - Chemistry
document_store_str 1
active_str 0
description 22 zwitterionic compounds (10 short-chain surfactants; 12 non-surfactants) were synthesised obeying the general formula R-N+(CH3)2(CH2)nSO3', where n = 2 to 4, by reacting the corresponding N, N-dimethylamines with either sodium-2-chloroethane sulfonate (n = 2), 1, 3- propanesulfonate (n = 3) or 1,4-butanesulfonate (n = 4). The R group varied from a C6 to C12 alkyl chain, to a phenylalkyl unit bearing a Cl to C4 chain and finally to a phenylpropyl unit with a C4 to C6 para-substituted alkyl group. Octanol/water partition coefficients of the 22 sulfobetaines were determined by a conventional stir-flask procedure. The amount of solute in both the octanol and water layer was quantified using a reverse-phase HPLC technique. A UV detection mechanism was employed for those sulfobetaines that possessed a suitable chromophore for UV detection and an electrospray ionisation mode of detection was used for the analysis of those sulfobetaines that lacked a chromophore suitable for UV detection. Acute aquatic toxicity to the aquatic invertebrate, Daphnia magna Straus, was reported as log (l/EC50). The EC50 values were determined experimentally using a standard Acute Immobilisation Test recommended by the OECD Guideline 202 and the internal Unilever document, Ecotoxicology SOP 019 11. A log P-based QS AR was then derived which was found to be analogous to the standard polar narcosis equation, suggesting that zwitterionic sulfobetaines act as polar narcotics. Experimental log P determined by the stir-flask procedure and the rules of Rekker and Roberts for the calculation of log P for quaternary ammonium compounds of the cationic type, were then used in the derivation of key fragment values and interaction factors for use in log P calculations of sulfobetaines using the Leo and Hansch approach. Furthermore, log P predictions provided by KowWin, a computerised program developed by the Syracause Research Cooperation, were suitably amended to take into consideration our experimental results. Finally, an investigation into the suitability of the phospholipophilicity parameter, log k'lAM, for defining aquatic toxicity was performed and the efficacy of using this parameter and log P to predict aquatic toxicity was compared. In addition, other chromatographic methods for estimating log P were investigated. These include the indirect reverse-phase HPLC method, the direct reverse-phase HPLC method and Counter Current Chromatography.
published_date 2003-12-31T09:46:05Z
_version_ 1851023493854920704
score 11.089677

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