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Determination of Critical Micellar Concentration of Homologous 2-Alkoxyphenylcarbamoyloxyethyl-Morpholinium Chlorides

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojárov 10, 83232 Bratislava, Slovakia
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Molecules 2018, 23(5), 1064; https://doi.org/10.3390/molecules23051064
Received: 16 March 2018 / Revised: 23 April 2018 / Accepted: 23 April 2018 / Published: 2 May 2018
(This article belongs to the Section Medicinal Chemistry)
The critical micellar concentrations of selected alkyloxy homologues of local anesthetic 4-(2-{[(2-alkoxyphenyl)carbamoyl]oxy}ethyl)morpholin-4-ium chloride with nc = 2, 4, 5, 6, 7, 8, and 9 carbons in alkyloxy tail were determined by absorption spectroscopy in the UV–vis spectral region with the use of a pyrene probe. Within the homologous series of the studied amphiphilic compounds, the ln(cmc) was observed to be dependent linearly on the number of carbon atoms nc in the hydrophobic tail: ln(cmc) = 0.705–0.966 nc. The Gibbs free energy, necessary for the transfer of the methylene group of the alkoxy chain from the water phase into the inner part of the micelle at the temperature of 25 °C and pH ≈ 4.5–5.0, was found to be −2.39 kJ/mol. The experimentally determined cmc values showed good correlations with the predicted values of the bulkiness of the alkoxy tail expressed as the molar volume of substituent R, as well as with the surface tension of the compounds. View Full-Text
Keywords: local anesthetic; morpholinium chloride; critical micellar concentration; pyrene absorption; sigmoidal Boltzmann equation local anesthetic; morpholinium chloride; critical micellar concentration; pyrene absorption; sigmoidal Boltzmann equation
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Stopková, L.; Gališinová, J.; Šuchtová, Z.; Čižmárik, J.; Andriamainty, F. Determination of Critical Micellar Concentration of Homologous 2-Alkoxyphenylcarbamoyloxyethyl-Morpholinium Chlorides. Molecules 2018, 23, 1064.

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