ISSN 1070-4272, Russian Journal of Applied Chemistry, 2008, Vol. 81, No. 3, pp. 452 454. Pleiades Publishing, Ltd., 2008.
Original Russian Text A.V. Babakhanyan, M.O. Manukyan, Zh.R. Babayan, R.S. Arutyunyan, 2008, published in Zhurnal Prikladnoi Khimii, 2008,
Vol. 81, No. 3, pp. 467 469.
ORGANIC SYNTHESIS
AND INDUSTRIAL ORGANIC CHEMISTRY
Antimicrobial Surfactants Based on
N,N -(5-Oxanona-2,7-diyne-1,9-diyl)bis[(alkoxycarbonylmethyl)-
dimethylammonium] Chlorides
A. V. Babakhanyan, M. O. Manukyan, Zh. R. Babayan, and R. S. Arutyunyan
Institute of Organic Chemistry, National Academy of Sciences of the Republic of Armenia, Yerevan, Armenia
Abovyan Armenian State Pedagogical University, Yerevan, Armenia
Yerevan State University, Yerevan, Armenia
Received May 15, 2007
Abstract A series of quaternary bisammonium salts containing the common 5-oxanonane-2,7-diyne-1,9-diyl
fragment and different alkoxycarbonylmethyl groups was synthesized. The surfactant properties and anti-
microbial activity of these compounds were studied.
DOI: 10.1134/S107042720803021X
Many practically important properties of surface-
active quaternary bisammonium salts depend on the
structure of the common group binding the terminal
alkylammonium groups. Among these compounds,
functionally substituted derivatives of mono- and
bisammonium salts containing unsaturated bonds are
of particular interest [1 3].
where R = C H (I), C H (II), C H (III), and
4 9 8 17 10 21
12 25
C H (IV).
Both the critical micelle concentration (CMC) of
quaternary ammonium salts (QAS) and the solution|air
interface characteristics of their aqueous solutions
were determined from the surface tension isotherms
obtained at T = 303 0.1 K by the technique reported
in [4].
Taking into account that ammonium salts with the
allyl and propargyl groups exhibit distinct anti-
microbial activity, in this study we synthesized bis-
ammonium salts containing, along with the alkoxy-
carbonylmethyl radicals ensuring surface activity, the
common 5-oxononane-2,7-diyne-1,9-diyl group (see
table).
These experiments showed that the QASs under
consideration are micelle-forming surfactants. As
the alkyl radicals in QAS molecules become longer,
both the critical micelle concentration and the surface
tension decrease, whereas the surface activity G in-
creases. As expected, the dependence of CMC on the
number n of carbon atoms in the alkyl radicals is
described by the well-known equation
These salts were prepared in high yields by the
following reactions:
HOCH C CH
HC CCH2Br +
NaOH
lnCMC = A
Bn,
2
where A and B are constants. These constants were
determined graphically from the equation logCMC =
f(n). Their values were found to be 2.7 and 0.16,
respectively.
HC CCH2OCH2C CH
FeCl , dioxane
(CH ) NH, CH O
3
3 2
2
The surface activity of the compounds under con-
sideration G was determined by the equation
(CH3)2 NCH2 C CCH2OCH2C CCH2N(CH3)2
Ethanol
ROCOCH Cl
2
G = (
CMC)/CMC,
Cl
Cl
0
+
+
(CH ) NCH2 C CCH2 OCH C CCH N(CH3 )2
,
3 2
2
2
where
is the surface tension of water, and
surface tension of aqueous QAS at CMC.
,
CMC
0
CH2 COOR
CH2 COOR
I IV
452