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The UV Spectroscopic Determination of Two Critical Micelle Concentrations of Domiphen Bromide in Solutions with KBr and Calculations of the Packing Parameter

UV-spektroskopische Bestimmung zweier kritischer Mizellbildungskonzentrationen von Domiphen-Bromid in Lösungen mit KBr und Berechnungen zum Packungparameter
B. Kopecká , T. Fazekaš , P. Kaclík and F. Kopecký

Abstract

Three different forms of the surface-active domiphen cations were detected by the UV spectroscopy in aqueous solutions of domiphen bromide, eventually with KBr additive. In sufficiently dilute solutions there are free domiphen cations, which aggregate into two types of micelles at two distinct concentrations, interpreted as the first and second critical micelle concentration, cmc and cmc2. From the logarithmic dependences of cmc and cmc2 on the bromide concentrations the corresponding degrees of counterion binding were estimated. Conformation analysis of the domiphen cation was performed and the packing parameters of the lowest energy conformers were calculated. The observed spectral shifts and the calculated packing parameters suggest that two conformers of domiphen cation with different arrangement of the phenoxyethyl group are responsible for the respective formation of two types of micelles.

Kurzfassung

Drei verschiedene Formen der oberflächenaktiven Domiphen-Kationen wurden durch UV-Spektroskopie in wässriger Lösung von Domiphen-Bromid und schließlich mit KBr-Additiven detektiert. In ausreichend verdünnten Lösungen sind freie Domiphen-Kationen vorhanden, die zu zwei Arten von Mizellen bei zwei verschiedenen Konzentrationen aggregieren, interpretiert als erste und zweite kritische Mizellbildungskonzentration (cmc und cmc2). Aus der logarithmischen Abhängigkeit der cmc und cmc2 von den Bromidkonzentrationen wurden die korrespondierenden Ausmaße der Gegenionenbindung berechnet. Eine Konformationsanalyse des Domiphen-Kations wurde durchgeführt und die Packungsparameter der energetisch niedrigsten Konformationen bestimmt. Die beobachteten Spektralverschiebungen und die berechneten Packungsparameter weisen darauf hin, dass zwei Konformationen des Domiphen-Kations, mit unterschiedener Anordnung der Phenoxyethyl-Gruppe, für die jeweiligen Formationen der zwei Arten von Mizellen verantwortlich sind.


Doc. František Kopecký, Department of Physical Chemistry of Drugs, Faculty of Pharmacy, Comenius University, 83232 Bratislava, Slovakia, Tel.: +4212 50117284, E-Mail:

Dr. Božena Kopecká graduated in 1964 from the Faculty of Pharmacy, Comenius University in Bratislava (Slovak Republic), and since that she has been working at the Department of Pharmaceutical Analysis and Nuclear Pharmacy of this Faculty. She completed postgraduate studies in Analytical Chemistry, for a number of years she was a senior research worker and now a senior lecturer. Her research field covers spectroscopic studies of various equilibriums in solutions, initially she studied the formation of metal complexes of Schiff bases and hydroxamic acids and more recently the formation of drug-cyclodextrin inclusion complexes, sorption on polymers and micellization of cationic surfactants.

Dr. Tomáš Fazekaš, born in 1966, graduated in 1989 from the Faculty of Natural Sciences, Comenius University in Bratislava (Slovak Republic) in the specialization of Physical Chemistry and afterwards he joint the Department of Physical Chemistry of Drugs of the Faculty of Pharmacy, Comenius University. Now he works at this Department as a part time senior lecturer and at the same time he has a full time managerial post in the Integrated Information System of the Faculty of Pharmacy. His research field is Theoretical Chemistry, especially calculations of solvent effects, and he has expertise in mathematical statistics and chemometrics.

Dipl.-Ing. Pavol Kaclík, born in 1963, graduated in 1986 from the Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava (Slovak Republic) in the specialization of Physical Chemistry and in 1991 he joint of the Department of Physical Chemistry of Drugs of the Faculty of Pharmacy, Comenius University in Bratislava, as a senior lecturer. He is engaged in the research of the drug-cyclodextrin complexation in solutions, surfactant micellization and he has expertise in the computerized laboratory measurements, data acquiring and processing systems.

Assoc. Prof. František Kopecký, born 1938, graduated in 1960 from the Faculty of Pharmacy, Masaryk University (Brno, Czech Republic), and later on he completed postgraduate studies in Physical Chemistry at the Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava (Slovak Republic). Since 1960 he has been working at the Department of the Physical Chemistry of Drugs of the Faculty of Pharmacy of the Comenius University in Bratislava, for more than two decades he was the head of this Department and now he works on a part-time basis. His research interests have been focused on thermodynamics of acid-base equilibriums and molecular association in solutions, hydrophobicity and partition of drugs, cyclodextrin complexes and surfactant micellization in connection with biological potency.


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Received: 2008-10-07
Revised: 2009-01-19
Published Online: 2013-04-02
Published in Print: 2009-05-01

© 2009, Carl Hanser Publisher, Munich

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