DOI: 10.1002/elps.200390120. Determination of octanol‐water partition coefficients for carbonate esters and other small organic molecules by microemulsion electrokinetic chromatography

Determination of octanol‐water partition coefficients for carbonate esters and other small organic molecules by microemulsion electrokinetic chromatography

10.1002/elps.200390120

Crossref journal-article

Wiley

ELECTROPHORESIS (311)

Abstract

AbstractMicroemulsion electrokinetic chromatography (MEEKC) was assessed as a tool for determination of octanol‐water partition coefficients using 34 solutes encompassing 8 carbonate esters. It was confirmed that microemulsions containing 1.44–2.88% w/w SDS, 6.49% w/w 1‐butanol, and 0.82% w/w n‐heptane constitute a good model of octanol‐water partitioning in the pH range of 1.4–7.4. Use of the migration index concept led to improved repeatability of the MEEKC method compared to the use of retention factors. Using a dynamical coating, a high electroosmotic flow at pH 1.4 and 4.75 was achieved expanding the practical pH working range of the MEEKC system. The correlation obtained between the migration index and log P was unaffected by pH indicating that the properties of the microemulsion droplets and, thus, partitioning are independent of pH. No evidence for congeneric behavior was found for the sample set comprising solutes with different hydrogen bonding properties suggesting that simple reference compounds can be used as calibrators. Lipophilicity estimates for the series of carbonate esters were obtained. The increase in lipophilicity with chain length was smaller than expected from the Hansch substituent constant, π.

Bibliography

Ãstergaard, J., Hansen, S. H., Larsen, C., Schou, C., & Heegaard, N. H. H. (2003). Determination of octanolâwater partition coefficients for carbonate esters and other small organic molecules by microemulsion electrokinetic chromatography. ELECTROPHORESIS, 24(6), 1038â1046. Portico.

Authors 5

Jesper Østergaard (first)
Steen Honoré Hansen (additional)
Claus Larsen (additional)
Christian Schou (additional)
Niels H. H. Heegaard (additional)

References 39 Referenced 37

10.1021/cr60274a001
10.1021/ja01062a035
10.1038/194178b0
{'key': 'e_1_2_1_5_2', 'first-page': '1', 'volume-title': 'Exploring QSAR. Fundamentals and Applications in Chemistry and Biology', 'author': 'Hansch C.', 'year': '1995'} / Exploring QSAR. Fundamentals and Applications in Chemistry and Biology by Hansch C. (1995)
10.1081/JLC-100103400
10.1016/S0021-9673(00)80213-7
10.1016/0021-9673(93)80814-O
10.1016/0021-9673(93)80815-P
10.1002/9783906390437.ch21
10.1002/9783527614998.ch5
{'key': 'e_1_2_1_12_2', 'first-page': '159', 'volume': '40', 'author': 'Poole C. F.', 'year': '2000', 'journal-title': 'Adv. Chromatogr.'} / Adv. Chromatogr. by Poole C. F. (2000)
10.1021/ac00066a015
10.1248/cpb.42.1525
10.1016/0378-4347(95)00082-T
10.1021/ac00100a009
10.1039/c39950002241
10.1016/0021-9673(95)00773-3
10.1016/0021-9673(96)00230-0
10.1021/ac971122l
10.1002/elps.1150191032
10.1016/S0378-4347(00)00072-4
10.1021/ac990852l
10.1016/S0021-9673(01)00573-8
10.1016/S0021-9673(01)01171-2
10.1016/0021-9673(96)00387-1
10.1021/ac00105a018
10.1016/S0021-9673(96)00518-3
10.1002/1522-2683(200107)22:12<2565::AID-ELPS2565>3.0.CO;2-I
{'key': 'e_1_2_1_30_2', 'first-page': '135', 'volume-title': 'Physical Pharmacy, 4th Ed.', 'author': 'Martin A.', 'year': '1993'} / Physical Pharmacy, 4th Ed. by Martin A. (1993)
Advanced Chemistry Development Inc. Toronto Canada. http://www.acdlabs.com
10.1016/S0928-0987(00)00189-5
10.1021/ac00077a009
{'key': 'e_1_2_1_34_2', 'first-page': '1', 'volume-title': 'Exploring QSAR. Hydrophobic, Electronic, and Steric Constants', 'author': 'Hansch C.', 'year': '1995'} / Exploring QSAR. Hydrophobic, Electronic, and Steric Constants by Hansch C. (1995)
10.1021/ac9510402
10.1016/S0021-9673(01)01383-8
10.1016/0021-9673(94)00686-5
{'key': 'e_1_2_1_38_2', 'first-page': '237', 'volume-title': 'Comprehensive Medicinal Chemistry. Volume 6. Cumulative Drug Index & Drug Compendium', 'author': 'Craig P. N.', 'year': '1990'} / Comprehensive Medicinal Chemistry. Volume 6. Cumulative Drug Index & Drug Compendium by Craig P. N. (1990)
Kortüm G. Vogel W. Andrussow K. in: International Union of Pure and Applied Chemistry (Ed.) Dissociation Constants of Organic Acids in Aqueous Solution Butterworth & Co. London 1961 pp. 190‐536 (10.1351/pac196001020187)
10.1002/hlca.19980810214

Dates

Type	When
Created	22 years, 5 months ago (March 20, 2003, 10:58 a.m.)
Deposited	1 year, 11 months ago (Sept. 12, 2023, 1:18 a.m.)
Indexed	1 year, 3 months ago (May 31, 2024, 8:49 p.m.)
Issued	22 years, 6 months ago (March 1, 2003)
Published	22 years, 6 months ago (March 1, 2003)
Published Online	22 years, 5 months ago (March 19, 2003)
Published Print	22 years, 6 months ago (March 1, 2003)

Funders 0

None

BibTeX

@article{_stergaard_2003, title={Determination of octanol‐water partition coefficients for carbonate esters and other small organic molecules by microemulsion electrokinetic chromatography}, volume={24}, ISSN={1522-2683}, url={http://dx.doi.org/10.1002/elps.200390120}, DOI={10.1002/elps.200390120}, number={6}, journal={ELECTROPHORESIS}, publisher={Wiley}, author={Østergaard, Jesper and Hansen, Steen Honoré and Larsen, Claus and Schou, Christian and Heegaard, Niels H. H.}, year={2003}, month=mar, pages={1038–1046} }

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