International Scholarly Research Network

ISRN Physical Chemistry

Volume 2012, Article ID 835397, 6 pages
doi:10.5402/2012/835397

Research Article
Hysteresis of Isotherms of Mixed Monolayers of
N -Octadecyl-N -phenylthiourea and Stearic Acid at
Air/Water Interface
Siji Sudheesh, Jamil Ahmad, and Girija S. Singh
Department of Chemistry, University of Botswana, PB 00704, Gaborone, Botswana
Correspondence should be addressed to Jamil Ahmad, ahmadj@mopipi.ub.bw
Received 11 October 2012; Accepted 2 December 2012
Academic Editors: J. J. Lopez Cascales, G. Pellicane, and P. O. Westlund
Copyright 2012 Siji Sudheesh et al. This is an open access article distributed under the Creative Commons Attribution License,
which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Surface pressure area isotherms of Langmuir monolayers formed by spreading mixed solutions of varying concentrations of Noctadecyl-N  -phenylthiourea (OPT) and octadecanoic acid or stearic acid (SA) over air-water interface are described. Examination
of the hysteresis behavior and an analysis of the limiting area per molecule of the isotherms show that when the spread solution has
an excess of OPT, the limiting surface area is consistent with a monolayer composed of equimolar amounts of the two components.
This indicates that any excess thiourea, which on its own does not form a stable monolayer, is squeezed out and is not part of the
monolayer. On the other hand, when the spreading mixture has an excess of SA over OPT, the isotherm indicates that the entire
originally spread material is incorporated into the surface film. In this case, the values of area/molecule indicate that the monolayer
is composed of SA : OPT complex with a ratio of 1 : 1 together with the excess SA remaining in the monolayer.

1. Introduction
Single component and mixed Langmuir monolayers at airwater interface continue to be of interest because they
provide a model for studying ordering in two dimensions
[1], they serve as precursors to Langmuir-Blodgett (LB)
films [24], and they are used to incorporate nanoparticles
[514] into LB films. They can also serve as templates
for two-dimensional crystal growth [1519] and they can
be used to control crystal nucleation [2027]. They also
serve as model systems for simulation of physicochemical
properties at interfaces. In research on mixed monolayers,
the study of interactions between the individual components,
miscibility among the components, mutual interaction, and
phase behavior are areas of interest [2834]. Our group
has been investigating interactions between components
of mixed monolayers and between monolayers and the
subphase with an objective to examine and control the
reactivity in various systems such as the monolayer of
monoterpenoid alcohol, nerol, over acidic subphase [35],
of 1-phenyl-1-hexadecanol over chromic acid [36], mixed

monolayers of octadecylamine and 1-octadecanethiol [37],

and several others [3842].
Some substances that do not form stable monolayers
by themselves are able to form mixed Langmuir films
with certain amphiphiles. Thus long-chain n-alkanes and
haloalkanes, which do not form monolayers on their own
because of their strong hydrophobic character, can remain at
the interface when mixed with suitable film-forming material
[4345]. Similarly some dicarboxylic acids have high solubility and pass into the aqueous subphase when added alone
to air-water interface, but form mixed monolayers with filmforming substances because of the interaction between them
[46].
In continuation of these studies, investigation of the
interaction between a long-chain thiourea and a fatty acid
was considered pertinent. The mechanism of interaction
between thiourea and other substances within and across
membranes would be of interest because thioureas constitute
a well-known class of molecules with biological importance
[47]. Disubstituted thioureas are known to interact with
several bioorganic molecules resulting in diverse types of

ISRN Physical Chemistry

S
N
H

36

N
H

OPT : SA 0.504 : 0.496

biological activity such as anticancer activity against various

types of leukemia and solid tumors [47], activity on the
central nervous system [48], antimycobacterial activity [49],
and antimicrobial activity [50].

2. Experimental
2.1. Materials. Commercial stearic acid (SA) (90%, UnivAR,
South Africa) was recrystallized from n-hexane, and a
3.585 103 M solution of it was prepared in n-hexane. OPT
(Figure 1) was synthesized by the reaction of phenylisothiocyanate (1) (98%, Acros Organics, USA) and octadecan-1amine (2) (98%, Aldrich chemicals) following the reported
method [51]. A solution of 5.0 mmol each of (1) and (2)
in 25 mL of distilled ethanol was refluxed for 30 min in a
100 mL round-bottom flask. The white solid product (OPT)
obtained after allowing the solution to attain the room
temperature was filtered under suction and recrystallized
from distilled ethanol three times. The melting point of
the crystalline product was 87.388.1 C. The product was
characterized by satisfactory spectral data [IR (Perkin-Elmer
Spectrum 100 FTIR) cm1 : 3233 (NH), 3054 (Ar CH),
1346 (C=S); 1 H NMR (CDCl3 , ppm): 7.777.65 (br, 1H,
NH), 7.48 (t, 2H, arom.), 7.35 (m, 1H, arom.), 7.25 (d, 2H),
6.09 (br, 1H, NH), 1.86 (t, 2H, NCH2 ), 1.60 (m, 2H, CH2 ),
1.30 (s, 30H, fifteen methylene protons), 0.92 (t, 3H, CH3 );
13 C NMR (CDCl , ppm): 180.7 (C=S), 136.1, 130.3, 127.4,
3
125.3 (Four arom. carbons), 45.7 (NCH2 ), 31.9, 29.7, 29.6,
29.55, 29.5, 29.4, 29.2, 29.0, 26.9, 22.7, 14 (CH3 )].
For monolayer studies, a 4.043 103 M solution of OPT
was prepared in chloroform.
2.2. Method. The film balance used for the measurements
was manufactured by Nima Technology, Coventry, England.
The trough was made from a single slab of PTFE with
two PTFE barriers. Near one barrier was a measuring
balance with a Wilhelmy plate cut from a filter paper, which
dipped into the aqueous phase. The force on the plate was
measured by a microbalance, which displayed the reading
on a computer screen. The monolayer was compressed at
a speed of 10 cm2 /min. The instrument displayed a graph
between the area available to the monolayer and the surface
pressure.
The inside of the trough was cleaned with soapy water,
followed by thorough rinsing with distilled water. It was
then cleaned with n-hexane using tissue paper. Finally it
was thoroughly rinsed with triply distilled water, which was
prepared by taking distilled water and redistilling it in a twostage all-quartz still.
The measurements were made at a constant temperature
of 25 C, by allowing the substrate water to come to this
temperature by storing it in a water bath. Blank runs on pure

(mN m 1 )

Figure 1: Structure of N-octadecyl-N  -phenylthiourea (OPT).

24

12

0
80

120

160

200

Area (cm2 )

Figure 2: Surface pressure area hysteresis isotherms of premixed

OPT/SA monolayers of approximately equimolar composition at
25 C. Recompression of the monolayer after the first compression
and expansion does not retrace the first cycle. The second and
subsequent cycles, however, coincide.

water and with spread pure solvent were made to ensure that
there was no surface impurity.
The sample containing the monolayer-forming material
was spread on the surface using a micro syringe. Appropriate
quantities of SA and OPT solutions were premixed and
spread on the subphase. The solvent was allowed to evaporate
and the monolayer was compressed to get the surface
pressure area per molecule (-A) isotherm.

3. Results and Discussion

OPT alone does not form a stable monolayer. The isotherm
of stearic acid has been reported earlier by other workers
[52, 53]. The curve shows that when the surface pressure is
around 49 mN/m, it decreases sharply, indicating a collapse.
With further compression, the surface pressure essentially
remains constant.
The behavior of a monolayer formed by spreading an
equimolar mixture of the two components and subjected to
repeated compression-expansion cycles is shown in Figure 2.
The initial compression is the right-most trace in the diagram. As the monolayer is compressed initially the behavior
is that of a liquid expanded film. Around a surface pressure
of 15 mN/m the curve starts to flatten out indicating a phase
transition. As the area available to the film is decreased
further, the surface pressure starts to rise steeply again.
When the monolayer is reexpanded from a value of
surface pressure of around 38 mN/m, there is a steep drop
in the surface pressure to around 8 mN/m, followed by a
gentler drop to about zero. On recompression the surface
pressure increases but the second cycle does not retrace the
curve of the first one. During the second cycle, the area
per molecule is much smaller and the phase change that
was pronounced during the first compression has largely
disappeared. The expansion curve, however, follows the path
of the first expansion.

ISRN Physical Chemistry

36
36

OPT : SA 0.888 : 0.112

24
(mN m 1 )

(mN m 1 )

OPT : SA 0.601 : 0.399

12

0
80

120

160

200

Area (cm2 )

12

0
50

90

130

170

Area (cm2 )

Figure 3: Surface pressure area hysteresis isotherms of premixed

OPT/SA monolayers with mole fraction ratio about 0.6 : 0.4.

Subsequent cycles largely coincide with the second cycle

indicating that it was during the first compression that
changes took place in the monolayer, and the state of
the monolayer is largely preserved through the subsequent
compression-expansion cycles. The indication is that the film
has reached a stable state and the composition of the monolayer remains unchanged during subsequent compressions
and expansions.
The behavior of the monolayer formed by spreading a
0.6 : 0.4 OPT : SA mixture is similar and is shown in Figure 3.
The monolayers formed by spreading mixtures containing a mole fraction of SA 0.4 and above showed a plateau
region around 1417 mN/m. This plateau region may be due
to an intermolecular proton transfer from the carboxylic acid
to thiocarboxamide functional groups of adjacently located
molecules. The attraction between the resulting ions draws
them closer reducing the area, which shows as the flat region.
R1 COOH + R2 NHCSNHC6 H5
R1 COO + R2 NHCSNH2 + C6 H5

24

(1)

(R1 = nC17 H35 , R2 = nC18 H37 )

This proton transfer can lead to a new monolayer phase
and the behavior of which does not correspond to either a
pure OPT or to a pure SA monolayer.
When OPT in the spreading mixture is in excess;
however, the isotherms do not fully coalesce even after
several cycles. In such monolayers, successive compressionexpansion cycles progressively shift towards a lower area,
indicating that the monolayer is progressively losing film
material. By noting that this loss does not take place when
SA is in excess, we can conclude that it is OPT which is
being squeezed out of the interface. The dierence between
the positions of the isotherms for successive cycles, however,
becomes smaller with each new cycle till the curves nearly
coincide as shown in Figure 4.
The limiting area of the composite film is obtained by
extrapolating the straight line portion of the coinciding
isotherm to zero pressure. Three quantities were calculated:

Figure 4: Surface pressure area hysteresis isotherms of monolayer

formed by spreading a premixed OPT/SA solution of the molar ratio
0.9 : 0.1, over water at 25 C.

total limiting area per molecule deposited, total limiting area

per stearic acid molecule deposited, and total limiting area
per OPT molecule deposited. A comparison of these three
quantities allows the estimation of the relative amount of
each of the components in the monolayer, assuming that all
the stearic acid deposited remains in the monolayer.
The monolayer formed by depositing equimolar mixture
of the two components gives coinciding curves after the
first compression, indicating that there is negligible loss
of film material through repeated compression-expansion
cycles. This shows that all the material deposited on the
interface remains incorporated in the monolayer in this case
and the equilibrium state of the monolayer is achieved just
after the first compression. Since the area per molecule is
known for stearic acid in a monolayer of pure stearic acid, the
total area occupied by stearic acid in the mixed monolayer
can be calculated. The area per molecule of OPT can then
be calculated by subtracting this value from the total area
occupied by the mixture of stearic acid and OPT. The value
of the area per molecule allows us to calculate the amount of
OPT remaining on the surface for those mixed films where
some of OPT is squeezed out of the monolayer before a stable
monolayer is formed.
In the equimolar mixed film, the limiting area per
molecule is found to be close to the area/molecule of a
pure stearic acid monolayer. Moreover the limiting area
of the mixed equimolar film divided by the number of
molecules of stearic acid alone is found to be twice the
area/molecule in the pure stearic acid film. This indicates
that half the area in the mixed film is occupied by the
molecules of each component. This is as to be expected since
both the molecules have similar hydrophobic chain. Thus,
total area/molecule OPT = total area/molecule stearic acid =
2(area/(molecule stearic acid + OPT)).
This leads us to conclude that the composition of the
film is 1 : 1 and all OPT molecules are incorporated in the
monolayer in the equimolar film.

ISRN Physical Chemistry

Table 1: Limiting area/molecule of OPT/SA premixed monolayer for coinciding curves.

Mole fraction of OPT : SA

in the spreading mixtures

Area/total deposited OPT

and SA molecules (A 2 )

Area/SA molecules added

(A 2 )

5.69
14.8
17.1
19.0
19.9
19.7

50.6
48.1
42.7
38.4
31.8
25.2

60

30
20
10
0
0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

Mole fraction SA in spreading mixture

Figure 5: Area per molecule assuming the monolayer comprises

1 : 1 complex and excess SA versus mole fraction of SA in the
spreading mixture. Any excess OPT is assumed removed from the
monolayer. The solid line indicates constant area/molecule. At low
mole fractions of SA deviation sets in from the constant value
obtained at mole fractions of SA 0.4 or higher.

This 1 : 1 composition is confirmed by the behavior of

the monolayer spread from solutions of other compositions.
Table 1 shows the observed limiting areas per molecule for
other compositions.
The values of area/molecule shown in the last column
are about constant for all monolayers that achieve a stable
reproducible form when subjected to several compressionexpansion cycles. Deviation from the constant value sets
in for those mixtures where OPT is in large excess. It is
noteworthy that for these monolayers, hysteresis curves do
not coincide. Figure 5 depicts this deviation graphically; the
solid line in the figure represents constant value of the
area/molecule obtained on the basis of those monolayers
where SA was in excess.
3.1. OPT Excess. For a monolayer formed by spreading OPT
and stearic acid in the ratio 0.8 : 0.2 mole fractions only
as many molecules of OPT will be incorporated into the
1 : 1 complex as are the molecules of stearic acid. The rest
will be removed from the film. With repeated cycles of the
hysteresis curves, excess OPT is progressively removed. A
stage is reached when successive hysteresis curves coincide
and the remaining monolayer remains stable. The observed
area/molecule at this equilibrium stage should be about one
half of the available area divided by the number of stearic
acid molecules. As Table 1 shows, this is what is observed
experimentally for the spread mixtures with an excess of
OPT. For the mixtures in which OPT is vastly in excess

(mN m 1 )

Area/molecule in 1 : 1
complex (A 2 /molecule)

0.888 : 0.112
0.693 : 0.307
0.601 : 0.399
0.504 : 0.496
0.372 : 0.628
0.220 : 0.780

Area/molecule remaining in
monolayer, assuming a 1 : 1 complex
plus any excess SA (A 2 )
25.3
24.1
21.4
19.2
19.9
19.7

40

20

0
60

100

140
Area (cm2 )

180

Figure 6: Surface pressure area hysteresis isotherm of stearic acid

spread over air/water interface at 25 C.

(0.8 : 0.2 and 0.9 : 0.1), successive curves do not fully coincide
even after several cycles, though they get closer. This explains
why the values of area per molecule start deviating from the
values for other compositions as the excess of OPT becomes
large, as shown in Figure 5. Keeping in view the fact that for
0.9 : 0.1 mixture the calculation assumes that ninth of the
amount of OPT deposited remains in the film as part of the
1 : 1 complex and ignores the rest, the closeness of the area
per molecule is remarkable. This is further confirmation of
1 : 1 complex.
3.2. SA Excess. The result of the film formed by spreading
mixtures where stearic acid is in excess is in accordance
with the conclusions outlined above. When stearic acid is in
excess, the hysteresis curves show a reversible behavior after
the first compression as shown in Figure 2. The value of the
limiting area per molecule can only be explained by assuming
that all OPT remains in the monolayer. This value is also
consistent with all OPT molecules being incorporated in a
1 : 1 complex with excess stearic acid molecules remaining at
the surface.
Figure 6 shows hysteresis curves for pure SA, which were
obtained for the purpose of comparison. Except for the
expected loss of some film material over time, all the cycles
show similar behavior.

ISRN Physical Chemistry

The pure SA isotherm is a smoothly rising curve with
a lift o area 20.2 A 2 and collapsed at about 49 mN/m. A
transition to a steeper portion of the curve occurred at
about 25 mN/m indicating the attainment of solid phase. The
area/molecule of pure SA was 20.0 A 2 at 25 mN/m.

4. Conclusion
N-Octadecyl-N  -phenylthiourea does not form a stable
monolayer on air-water interface but when spread together
with stearic acid, it can get incorporated into the monolayer.
Hysteresis measurements on such mixed monolayers show
that the area/molecule is consistent with the monolayer
having a 1 : 1 composition of the two components in addition
to any excess stearic acid deposited. For monolayers which
are formed by spreading mixtures containing excess of the
thiourea, the values correspond to a simple 1 : 1 mixture with
excess thiourea not remaining in the monolayer.

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