Reference

New amino acid-based anionic surfactants and their use as enantiodiscriminating lyotropic liquid crystalline NMR solvents

New amino acid-based anionic surfactants and their use as enantiodiscriminating lyotropic liquid crystalline NMR solvents. Baczko, Krystyna; Larpent, Chantal; Lesot, Philippe (CNRS UMR 8086, SIRCOB, Interactions et Reactivite en Chimie Organique et Bioorganique, Laboratoire de Synthese, Universite de Versailles St-Quentin en Yvelines, Versailles 78035, Fr.). Tetrahedron: Asymmetry, 15(6), 971-982 (English) 2004 Elsevier Science B.V. CODEN: TASYE3. ISSN: 0957-4166. 31024-91-6 is the cas registry number. This chemical is also mentioned in this article. DOCUMENT TYPE: Journal CA Section: 34 (Amino Acids, Peptides, and Proteins) Section cross-reference(s): 66 New amino acid-based anionic surfactants, 2-NaO3SC6H4CO-Xaa-O(CH2)nMe (Xaa = L-Phe; n = 4, 7, 9, 11, 13; Xaa = L-Ala; n = 11), have been synthesized and were studied for their use as chiral oriented NMR solvents. These L-Phe or L-Ala derivs. were prepd. by reacting the corresponding amino acid esters with o-sulfobenzoic anhydride. Their crit. micelle concns. (CMCs) range from 1.6 ′ 10-5 to 1.4 ′ 10-2 mol/L and depend on the alkyl chain length as well as on the type of the amino acid. These values are comparatively lower than those of classical surfactants such as alkylbenzenesulfonates and N-acylamino acid carboxylates. The title compds. are also examd. for their uses as chiral liq. crystals (CLC) for anal. purposes. For example, it is shown that aq. solns. of these chiral sulfonates in the presence of chlorinated solvents (CHCl3, CH2Cl2, C2H2Cl4, CCl4) enable homogeneous oriented NMR solvents to differentiate between enantiomers of D,L-alanine-2-d1 using proton and deuterium NMR spectroscopy. .