Chiroptical Phenomena in Reverse Micelles: The Case of (1R,2S)-Dodecyl (2-hydroxy-1-methyl-2-phenylethyl)dimethylammoniumBromide (DMEB)

Angela Monia Ruggirello, Vincenzo Turco Liveri, Marco Passarello, Daniele Mendola, Vincenzo Turco Liveri, Franca Castiglione, Angela Ruggirello, Sergio Abbate, Giovanna Longhi, France Lebon, Fiorenza Viani, Andrea Mele

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Abstract

(1R,2S)-Dodecyl(2-hydroxy-1-methyl-2-phenylethyl)dimethylammonium bromide(DMEB) aggregates dispersed in carbon tetrachloride have been investigated by Fourier transforminfrared (FT-IR), vibrational circular dichroism (VCD) and 1H nuclear magnetic resonance (NMR)spectroscopy at various surfactant concentration and water-to-surfactant molar ratio. Experimentaldata indicate that, even at the lowest investigated concentration and in absence of added water,DMEBmolecules associate in supramolecular assemblies. At higherDMEBconcentration the aggregatescan confine watermolecules,making it plausible to think thatDMEB form reverse micelles andthat watermolecules are quite uniformly distributed among them andmainly located in the proximityof surfactant head groups.Moreover, the water state in DMEB reverse micelles has been found to bedifferent from that in pure water, due to system-specific water/surfactant head group interactions. 1HNMR diffusion measurements of both water and DMEB emphasize their joined translational motioncharacterized by a diffusion rate one order of magnitude lower than that of free molecules. Finally,VCD allowed us to show some characteristics of the association of optically active DMEB moleculesas reverse micelles and water confinement inside; namely, we monitored the vibrational opticalactivity of deuterated hydroxyl bonds of the self-assembled DMEB molecules and their interactionwith D2Omolecules
Original languageEnglish
Pages (from-to)1-10
Number of pages10
JournalChirality
Volume1
Publication statusPublished - 2014

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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    Ruggirello, A. M., Turco Liveri, V., Passarello, M., Mendola, D., Turco Liveri, V., Castiglione, F., Ruggirello, A., Abbate, S., Longhi, G., Lebon, F., Viani, F., & Mele, A. (2014). Chiroptical Phenomena in Reverse Micelles: The Case of (1R,2S)-Dodecyl (2-hydroxy-1-methyl-2-phenylethyl)dimethylammoniumBromide (DMEB). Chirality, 1, 1-10.