Synthesis and characterization of optically active surfactants derived from phenylalanine and leucine

M J Diego-Castro; H C Hailes; M J Lawrence

doi:10.1006/jcis.2000.7285

Synthesis and characterization of optically active surfactants derived from phenylalanine and leucine

M J Diego-Castro, H C Hailes, M J Lawrence

Institute of Pharmaceutical Science

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

Two optically active cationic surfactants, (2S)-N-hexadecyl-N, N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium chloride 1 and (2S)-N-hexadecyl-N,N-dimethyl-(l-hydroxy-4-methylpentyl)-2-ammonium chloride 2, have been selected and synthesized for use as enantioselective micellar catalysts in aqueous media. Their surface and aggregation behavior has been investigated at 298 K using surface tension and light scattering studies, which revealed that both molecules associate at low concentrations to produce micellar aggregates. Interestingly, although the area per molecule occupied by the surfactants at the air-water interface (43.6 Angstrom (2) for 1 and 54.6 Angstrom (2) for 2) is similar to that of related cationic surfactants, their aggregation number (23 for 1 and 19 for 2) is much smaller, perhaps reflecting the influence of the size or homochiral nature of the head group in the packing of the micelle. (C) 2001 Academic Press.

Original language	English
Pages (from-to)	122 - 126
Number of pages	5
Journal	JOURNAL OF COLLOID AND INTERFACE SCIENCE
Volume	234
Issue number	1
DOIs	https://doi.org/10.1006/jcis.2000.7285
Publication status	Published - 1 Feb 2001

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title = "Synthesis and characterization of optically active surfactants derived from phenylalanine and leucine",

abstract = "Two optically active cationic surfactants, (2S)-N-hexadecyl-N, N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium chloride 1 and (2S)-N-hexadecyl-N,N-dimethyl-(l-hydroxy-4-methylpentyl)-2-ammonium chloride 2, have been selected and synthesized for use as enantioselective micellar catalysts in aqueous media. Their surface and aggregation behavior has been investigated at 298 K using surface tension and light scattering studies, which revealed that both molecules associate at low concentrations to produce micellar aggregates. Interestingly, although the area per molecule occupied by the surfactants at the air-water interface (43.6 Angstrom (2) for 1 and 54.6 Angstrom (2) for 2) is similar to that of related cationic surfactants, their aggregation number (23 for 1 and 19 for 2) is much smaller, perhaps reflecting the influence of the size or homochiral nature of the head group in the packing of the micelle. (C) 2001 Academic Press.",

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T1 - Synthesis and characterization of optically active surfactants derived from phenylalanine and leucine

AU - Diego-Castro, M J

AU - Hailes, H C

AU - Lawrence, M J

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Y1 - 2001/2/1

N2 - Two optically active cationic surfactants, (2S)-N-hexadecyl-N, N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium chloride 1 and (2S)-N-hexadecyl-N,N-dimethyl-(l-hydroxy-4-methylpentyl)-2-ammonium chloride 2, have been selected and synthesized for use as enantioselective micellar catalysts in aqueous media. Their surface and aggregation behavior has been investigated at 298 K using surface tension and light scattering studies, which revealed that both molecules associate at low concentrations to produce micellar aggregates. Interestingly, although the area per molecule occupied by the surfactants at the air-water interface (43.6 Angstrom (2) for 1 and 54.6 Angstrom (2) for 2) is similar to that of related cationic surfactants, their aggregation number (23 for 1 and 19 for 2) is much smaller, perhaps reflecting the influence of the size or homochiral nature of the head group in the packing of the micelle. (C) 2001 Academic Press.

AB - Two optically active cationic surfactants, (2S)-N-hexadecyl-N, N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium chloride 1 and (2S)-N-hexadecyl-N,N-dimethyl-(l-hydroxy-4-methylpentyl)-2-ammonium chloride 2, have been selected and synthesized for use as enantioselective micellar catalysts in aqueous media. Their surface and aggregation behavior has been investigated at 298 K using surface tension and light scattering studies, which revealed that both molecules associate at low concentrations to produce micellar aggregates. Interestingly, although the area per molecule occupied by the surfactants at the air-water interface (43.6 Angstrom (2) for 1 and 54.6 Angstrom (2) for 2) is similar to that of related cationic surfactants, their aggregation number (23 for 1 and 19 for 2) is much smaller, perhaps reflecting the influence of the size or homochiral nature of the head group in the packing of the micelle. (C) 2001 Academic Press.

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DO - 10.1006/jcis.2000.7285

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ER -

Synthesis and characterization of optically active surfactants derived from phenylalanine and leucine

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