Modulation of aggregation behavior, antimicrobial properties and catalytic activity of piperidinium surfactants by modifying their head group with a polar fragment

Modulation of aggregation behavior, antimicrobial properties and
catalytic activity of piperidinium surfactants by modifying their head
group with a polar fragment
Rushana A. Kushnazarova a, Alla B. Mirgorodskaya a,⇑, Denis M. Kuznetsov a, Anna A. Tyryshkina b,
Alexandra D. Voloshina a, Sumbela K. Gumerova a, Oxana A. Lenina a, Eugeny N. Nikitin c, Lucia Ya.
Zakharova a
a Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, 8, Arbuzov str., 420088 Kazan, Russian Federation
b Kazan Federal University, 18, Kremlyovskaya str., 420008 Kazan, Russian Federation
c FRC Kazan Scientific Center of RAS, 2/31, Lobachevskii str., 420011 Kazan, Russian Federation
a r t i c l e i n f o
Article history:
Received 16 March 2021
Accepted 23 April 2021
Available online 28 April 2021
Keywords:
Piperidinium surfactants
Aggregation
Antimicrobial activity
Ester
Hydrolysis
Micellar catalytic effect
a b s t r a c t
To establish the effect of surfactants structure on their functional activity a number of alkyl-N-hydroxye
thylpiperidinium bromides with different length of the hydrophobic tail were synthesized and characterized.
Aggregation parameters of these surfactants were determined using tensiometry and fluorimetry. It
was shown that the piperidinium surfactants, including those functionalized with OH groups, show a
high antimicrobial effect at concentrations lower than critical micelle concentration for both bacteria
and fungi, with the low hemolytic activity revealed. In addition, these surfactants were studied as micellar
catalysts in alkaline hydrolysis of carboxylic acid esters. Micellar catalytic effect increases with an
growth in the length of the alkyl tail, as well as with an increase in the number of hydroxy groups in surfactant
molecule and can exceed two orders of magnitude.