Original Acta Chromatographica 27(2015)3, 399–411

Research Paper DOI: 10.1556/AChrom.27.2015.3.1

Evaluation of Some Empirical Retention

Models for High Submicellar Liquid
Chromatographic Separation of Aromatic
Diamines
M.R. HADJMOHAMMADI AND S.S.S.J. NAZARI*
Department of Chemistry, University of Mazandaran, P.O. Box 453, Babolsar, Iran
*E-mail: s.nazari@umz.ac.ir

Summary. Description of the retention of five aromatic diamines in high submicellar

liquid chromatography was carried out through several hyperbolic and logarithmic re-
tention models using the retention data of mobile phases consisting of sodium dodecyl
sulfate (SDS) (0.09–0.15 M) and methanol (50–70% v/v) at pH 3. Among the investigated
models, the logarithmic retention model log k = c0 + c1ϕ + c2 [ M ] + c12 (ϕ[ M ])0.5 showed the
best prediction capability and used to predict the solutes retention factors. The mean
relative error of the prediction of retention factors of five aromatic diamines in the se-
lected variables space was lower than 0.5%. Based on the best retention model, a grid
search program was used to predict the retention times of each solute for all combina-
tions of SDS and methanol concentrations in the factor space. In order to find optimal
separation condition, two different chromatographic goals, analysis time and retention
differences between adjacent peaks, were evaluated simultaneously using Derringer's
desirability function for each mobile phase composition. At the optimal conditions (0.143
M SDS, 53% v/v methanol), a good agreement was observed between predicted and ex-
perimental values of the retention times (R2 = 0.9999 and mean relative error of 0.96%).

Key Words: high submicellar liquid chromatography, empirical retention modeling,

Derringer's desirability function, separation optimization, aromatic diamines

Introduction
Micellar liquid chromatography (MLC) is a reversed-phase liquid chroma-
tographic (RPLC) mode with a mobile phase consisting of an aqueous solu-
tion of surfactant above its critical micellar concentration (CMC). The popu-
larity of this mode of separation has increased because of several unique
advantages such as the simultaneous separation of ionic and nonionic com-
pounds, rapid gradient capability, possibility of direct injection of physio-
logical fluids, gradient compatibility with electrochemical detectors, en-
hanced luminescence detection, etc. Also, the stable and reproducible be-
havior of micellar mobile phases enables the accurate prediction of solutes
retention with a model that can be further used to optimize the separation
of mixtures of solutes [1, 2]. Most studies in MLC use a short-chain alcohol

0231–2522 © 2014 Akadémiai Kiadó, Budapest

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400 M.R. Hadjmohammadi and S.S.S.J. Nazari

such as methanol, propanol, butanol, or pentanol [1, 2] as an additive to mi-

cellar mobile phases to improve the peak shape and efficiency and increase
the elution strength [3, 4]. These organic modifiers decrease the mobile
phase polarity and affect the amount of surfactant adsorbed on the station-
ary phase; also, micelle parameters, such as the CMC and surfactant aggre-
gation number (i.e., number of surfactant monomers associated in a mi-
celle), are altered through addition of modifier [5–7].
In practice, the amount of organic solvent that can be added to a micel-
lar mobile phase is limited by its solubility and micelle disaggregation. It is
accepted that micelles are disrupted at concentrations (v/v) above 40%
methanol, 30% ethanol, 22% 1-propanol, and 30% acetonitrile [8, 9], but
these values are not conclusive. However, when the concentration of or-
ganic solvent is increased, there is no sudden breakdown of micelles, but a
progressive reduction in the aggregation number occurs [10]. When the
added organic solvent induced micelle breakdown, another chroma-
tographic mode has been distinguished in RPLC which was recently called
high submicellar chromatography (HSC) by Ruiz-Angel et al [9].
In HSC, the surfactant concentration is at level that the micelles are
formed in water and organic solvent concentration is also high to prevent
the formation of micelles. Consequently, in HSC, only surfactant monomers
exist in the mobile phase, which are dissolved in the hydro-organic me-
dium; also, the surfactant coating on the stationary phase is reduced signifi-
cantly compared to MLC [9, 11–15]. In this mode, ion-pair interactions be-
tween charged solutes and free surfactant monomers in the bulk solvent
will coexist with the ion exchange on the still surfactant-modified stationary
phase [9]. This surfactant-mediated RPLC mode was first used to separate
aromatic compounds by Li and Fritz [11] and Jandera et al. [12]. Recently,
the chromatographic performance of this mode has been perfectly described
for a group of basic drugs (β-blockers) [9, 13–15], aromatic diamines [16],
and some radio-metabolites [17]. The results of these studies showed attrac-
tive advantages of HSC with respect to other RPLC modes, in terms of effi-
ciency, peak shape, selectivity, and analysis time.
An interpretive optimization in liquid chromatography requires an ac-
curate description of the retention through retention models [18–20]. In
MLC, several empirical or mechanistic retention models have been devel-
oped which describe the retention behavior. In any case, the models allow a
reliable optimization of the separation conditions based on a reduced num-
ber of experiments [21–25]. In this study, the performance of the several hy-
perbolic and logarithmic empirical retention models, fitted with the reten-
tion data of five aromatic diamines (Fig. 1) in a two dimensional factor space
was investigated using acidified mobile phases containing the anionic sur-
factant sodium dodecyl sulphate (SDS) and methanol.

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Evaluation of Some Empirical Retention Models 401

Fig. 1. Molecular structure of five studied aromatic diamines:

(1) 1,5-naphthalenediamine; (2) 4-(4-aminophenyl) azoaniline; (3) 1,4-phenylenediamine;
(4) 4,4′-diaminobiphenyl; (5) 4,4′-diaminodiphenylmethane

Aromatic diamines are an important class of compounds applied in dif-

ferent fields of industry for making dyes and cosmetics [26, 27], particularly,
in the synthesis of a number of polymers [28–30]. Due to the toxic nature
and potential carcinogenic properties of these compounds, monitoring of
their levels in the environment is important for the protection of health and
the environment [26, 31–34]. Simultaneous optimization of separation qual-
ity and analysis time of selected aromatic diamines was carried out using
Derringer's desirability function [35–38] based on the predicted retention
times through the selected empirical retention model. For evaluation of the
predicted chromatograms, a chromatographic response function (CRF)
similar to the method proposed by Divjak et al. [36] was applied.

Experimental
Chemicals and Stock Solutions
Standards of 1,4-phenylenediamine, 1,5-naphthalenediamine, high-perfor-
mance liquid chromatography (HPLC) grade methanol, sodium dihydro-
genphosphate, and phosphoric acid was purchased from Merck (Darm-
stadt, Germany). 4,4′-Diaminodiphenylmethane, 4,4′-diaminobiphenyl, and

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402 M.R. Hadjmohammadi and S.S.S.J. Nazari

SDS were purchased from Fluka (Buchs, Switzerland). 4-(4-Aminophenyl)

azoaniline was obtained from Alfa Aesar (Karlsruhe, Germany). The water
used was double distilled deionized. Stock (500 mg L−1) and working (25
mg L−1) solutions of diamines were prepared in methanol and metha-
nol:water 50:50 (v/v), respectively. These solutions were kept in the dark at
4 °C and filtered through 0.45 μm syringe filter (Millipore, Bedford, MA,
USA) before use.

Apparatus and Software

An HPLC system consisted of a model 515 solvent delivery system from
Waters (Milford, MA, USA), model 7725i manual injector with a 20-μL loop
(Rheodyne, Cotati, CA, USA), a Perkin-Elmer LC-95 UV detector (Norwalk,
CT, USA) set at 254 nm, and a Spherisorb C18 column (250 mm × 4.6 mm,
10 μm particle size) from Waters was used for all the separations. The col-
umn was thermostated at 25 °C by a water circulator bath. Adjustment of
pH of solutions was carried out by model 3030 Jenway pH meter (Leeds,
UK). Microsoft Excel solver and Excel Visual Basic 2003 were used to fit the
retentions data to retention models and generation of grid search algorithm,
respectively.

Experimental Design and Chromatographic Conditions

The experimental design consisted of a two-factor space, covering five mo-
bile phases with different concentration domains of SDS and methanol:
0.09–0.15 M SDS/50–70% (v/v) methanol at pH 3. At these conditions, the
high concentration of methanol prevents the formation of micelles; there-
fore, only surfactant monomers exist in the mobile phase. The mobile
phases were acidified to keep the diamine in the protonated form. Repre-
sentative chromatograms of diamines at the corners of design space are
shown in Fig. 2. All mobile phases were buffered using 0.01 M NaH2PO4
and H3PO4, filtered through a 0.45-μm Millipore filter (Bedford, MA, USA),
degassed under vacuum, and passed through the column at flow rate 1.0
mL min−1. The retention times were obtained from double subsequent injec-
tions. Dead time value was measured from the time of injection of sample
solvent to the first significant deviation of the base line.

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Evaluation of Some Empirical Retention Models 403

Fig. 2. Representative chromatograms at the corners of variables space. Mobile phase

compositions: (a) 0.09 M SDS/50% methanol, (b) 0.15 M SDS/50% methanol, (c) 0.09 M
SDS/70% methanol, (d) 0.15 M SDS/70% methanol. Flow rate = 1.0 mL min−1, column
C18 (250 mm × 4.6 mm, 10 μm), injection volume = 20 μL, λ = 254 nm; 25 °C. Compounds:
(1) 1,5-naphthalenediamine; (2) 4-(4-aminophenyl) azoaniline; (3) 1,4-phenylenediamine;
(4) 4,4′-diaminobiphenyl; (5) 4,4′-diaminodiphenylmethane

Results and Discussion

Description of Retentions of Aromatic Diamines in HSC
In the literature, several empirical and mechanistic models are given for the
description of retention in MLC. A polynomial model that yields successful
descriptions in hybrid micellar mobile phase is the following [21, 22, 24]:

1 1 K MLC
= (1 + KADφ ) + AM (1 + K MDφ )[ M ]
k KAS KAS
(1)
= c0 + c1ϕ + c 2 [ M ] + c12ϕ[ M ]

Recently, Ruiz-Angel et al. proposed a mechanistic model to describe the re-

tention behavior of basic drugs (β-blocker) in HSC [13]:

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404 M.R. Hadjmohammadi and S.S.S.J. Nazari

1 1 Kφ K HSC
= (1 + KADφ ) + (1 + KADφ )φ 2 + AM (1 + K MDφ )[S ]
k KAS KAS KAS
(2)
= c0 + c1ϕ + c11ϕ 2 + c111ϕ 3 + c2 [S] + c12ϕ[S]

which is simplified to:

Kφ 2 KAM HSC
1 1
= (1 + KADφ ) + φ + (1 + K MDφ )[S ]
k KAS KAS KAS
(3)
2
= c0 + c1ϕ + c11ϕ + c2 [S] + c12ϕ[S]

where k is the retention factor ( (tR − t0 )/t0 ); tR and t0 are the retention time
and dead time, respectively; ϕ is the volume fraction of organic solvent in
the aqueous–organic mobile phase; c0 , c1 , c11 , c111 , c12 , and c 2 are regres-
sion coefficients with characteristic values for a given solute and col-
umn/solvent system; [M] is the concentration of surfactant monomers in-
volved in micelle formation, and [S] the concentration of surfactant mono-
mers in the HSC mode (where no micelles are formed); KAS describes the
partition of the solute between bulk water and the surfactant-modified sta-
MLC HSC
tionary phase, and KAM and KAM the partition between bulk water and
the surfactant monomers forming micelles (MLC) or the free monomers
(HSC); and KAD and K MD are constants that account for the displacement of
the partitioning equilibria produced by the addition of the organic solvent.
The quadratic and cubic terms in ϕ for the HSC models account for the lar-
ger role of the organic solvent in the mobile phase [9, 13–15]. The accuracy
of eqs. (1)–(3) to model the retention in the HSC has been previously
checked in the literature. The results showed that the description of reten-
tion of β-blocker using eq. (1) was not satisfactory. On the other hand, the
results improved significantly with both eqs. (2) and (3), but similar results
were obtained using both equations [13, 15].
In order to achieve adequate retention model for reliable description of
the retention of target aromatic diamines in the selected HSC region, the re-
tention data of each diamine eluted with the mobile phases described in Ex-
perimental Design and Chromatographic Conditions section were fitted to
eqs. (1) and (3) as well as the empirical retention models given in Table I.
The performance of the investigated models was measured using the square
of correlation coefficient ( R 2 ) and the mean relative prediction error (RE)
calculated as:

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Evaluation of Some Empirical Retention Models 405

∑
n
kexp − kpred
i =1
RE = × 100 (4)
nk exp

where kexp and kpred are the experimental and predicted retention factors, re-
spectively, for each individual compound eluted with each mobile phase,
and k exp is the mean experimental retention factor considering all com-
pounds and mobile phases. The values of ( R2 ) and (RE) are given in Table I.

Table I. Empirical retention models, square of correlation coefficient (R2) and mean
relative prediction error (RE) for prediction of retention factors of five aromatic diamines
in HSC eluted with mobile phase of SDS (0.09–0.15 M) and methanol
(50–70% v/v) at pH 3

Eq. f ([S],ϕ ) RE
Eq. R2
(n = 25)

aa 1/ k = c0 + c1ϕ + c2 [S ] + c12ϕ[S ] 0.9619 10.52

b 1/ k = c0 + c1ϕ + c2 [S ] + c12 (ϕ[S ])0.5 0.9802 7.34

c 1/ k = c0 + c1ϕ + c2 [S ] + c12ϕ[S ] + d12 (ϕ[S ])0.5 0.9892 4.97

d 1/ k = c0 + c1ϕ + c11ϕ 2 + c2 [S] 0.9891 6.85

e 1/ k = c0 + c1ϕ + c2 [S] + c22 [S]2 0.9933 4.61

fb 1/ k = c0 + c1ϕ + c11ϕ 2 + c 2 [S ] + c12ϕ[S ] 0.9996 0.82

g 1/ k = c0 + c1ϕ + c2 [S ] + c 22 [S ]2 + c12ϕ[S ] 0.9972 2.83

2 2
h 1/ k = c0 + c1ϕ + c11ϕ + c 2 [S ] + c 22 [S ] 0.9933 4.59
i log k = c0 + c1ϕ + c2 [S] + c12ϕ[S ] 0.9922 4.37
0.5
j log k = c0 + c1ϕ + c2 [S] + c12 (ϕ[S]) 0.9999 0.41

k log k = c0 + c1ϕ + c2 [S] + c12ϕ[S] + d12 (ϕ[S])0.5 0.9999 0.40

l log k = c0 + c1ϕ + c11ϕ 2 + c 2 [S ] 0.9596 11.82

m log k = c0 + c1ϕ + c2 [S] + c22 [S ]2 0.9615 10.90

2
n log k = c0 + c1ϕ + c11ϕ + c 2 [S ] + c12ϕ[S ] 0.9981 2.20

o log k = c0 + c1ϕ + c2 [S] + c22 [S]2 + c12ϕ[S] 0.9971 2.86

p log k = c0 + c1ϕ + c11ϕ 2 + c2 [S] + c22 [S]2 0.9610 11.52

k: retention factor; ϕ: volume fraction of methanol in mobile phase; [S]: concentra-

tion of SDS monomers in the HSC mode; ci: regression coefficients.
aEq. (1) in the text.
bEq. (3) in the text.

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406 M.R. Hadjmohammadi and S.S.S.J. Nazari

As it is observed, in the models consisting of quadratic terms [S]2 and

ϕ 2 (eqs. (d)–(h)), the results given by the logarithmic equations were poorer
than hyperbolic equations (eqs. (l)–(p)). In contrast, the logarithmic equa-
tions gave better prediction capability for the models containing terms ϕ [S]
and (ϕ [S])0.5 without quadratic terms (eqs. (i)–(k)). Among the investigated
hyperbolic models, the best model was eq. (f) with (R2) and (RE) values of
0.9996 and 0.82%, respectively, which is in accordance with the previous re-
ports [13, 15]. Additionally, the predictions were found to be highly satisfac-
tory using logarithmic models (eqs. (j) and (k)) with the (R2) and (RE) values
of 0.9999 and 0.41% for eq. (j) and 0.9999 and 0.40% for eq. (k), respectively.
Since the eq. (j) fits the retention data using one parameter less than eqs. (f)
and (k), this model was chosen as the suitable model for retention modeling
of interested diamines in investigated HSC region. The regression coeffi-
cient of eq. (j) and statistics for each solute are given in Table II. Description
of the retention of the diamines using eq. (j) was depicted in Fig. 3. A good
agreement observed between predicted and experimental retention factors
indicated that the model is quite successful in description of the retention
factors.

Fig. 3. Predicted versus experimental logarithm of retention factors for the five aromatic
diamines in high submicellar RPLC (0.09–0.15 M SDS/50–70% methanol). The
predictions were made with eq. (j) (represented in Table I)

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 Evaluation of Some Empirical Retention Models 407

Table II. The regression coefficients of selected retention model for prediction of diamines
retentions in HSC (eq. (j) log k = c0 + c1ϕ + c2 [ M ] + c12 (ϕ[ M ])0.5 )

Solutes
Coefficient
(1) (2) (3) (4) (5)

c0 +2.303 ± 0.055 +2.586 ± 0.05 +2.417 ± 0.009 +3.014 ± 0.012 +3.337 ± 0.001

c1 −0.075 ± 0.005 −0.089 ± 0.005 −0.089 ± 0.001 −0.090 ± 0.001 −0.092 ± 0.001

c2 −0.028 ± 0.003 −0.033 ± 0.002 −0.034 ± 0.001 −0.036 ± 0.001 −0.037 ± 0.001

c12 +0.070 ± 0.008 +0.085 ± 0.007 +0.090 ± 0.001 +0.089 ± 0.002 +0.091 ± 0.001
Statistics
R2 0.9993 0.9995 1.0000 1.0000 1.0000
2
R adj 0.9972 0.9980 1.0000 1.0000 1.0000
RE (n = 5) 1.55 0.02 0.17 0.01 0.01

Solute: (1) 1,5-naphthalenediamine; (2) 4-(4-aminophenyl) azoaniline;

(3) 1,4-phenylenediamine; (4) 4,4′-Diaminobiphenyl; (5) 4,4′-diaminodiphenylmethane.

Optimization of Separation of Diamines in HSC

A reliable optimization strategy requires accurate prediction of the retention
of solutes present in mixture in whole variable space. In order to predict the
retention times of diamines in studied HSC region, a grid search program
was written in Microsoft Office Excel 2003. Using this program, in 1280 dif-
ferent mobile phase compositions (SDS and methanol within the concentra-
tion range 0.09–0.15 M SDS and 50–70% v/v methanol), retention time of
each solute was calculated based on the best empirical retention model
(eq. (j)). Two different chromatographic criterions, separation quality and
analysis time, were evaluated simultaneously using Derringer’s desirability
function within the predicted retention times for each mobile phase compo-
sition. The method of Divjak et al. [36] was used to transform the chroma-
tographic criteria to desirability values, but the differences between reten-
tion times of neighboring peaks ( δ tR i , i +1 ) were employed instead of resolu-
tion as the measure of separation. Another criterion was the predicted re-
tention time of the most retained solute tR Max in each mobile phase compo-
sition. It was used as the measure of analysis time. Transformation of the
criterions values to desirability values ranging between 0 and 1 was per-
formed using sigmoidal equations described in our previous work [38],
where the minimum and maximum acceptable value of the δ tR i , i +1 was set
at 1.0 min and 2.5 min, respectively. Also, the limiting time for tR Max was
set at 20 and 45 min, respectively. The CRF (i.e., the desirability of the over-

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408 M.R. Hadjmohammadi and S.S.S.J. Nazari

all appearance of a chromatogram in regard to the resolution between five

analytes and the analysis time) was calculated by multiplying the final de-
sirability values for δ tR i , i +1 and tR Max .
The specific condition in variation pattern in the grid search, corre-
sponding to the maximum CRF value, was selected as the optimal point.
The optimal values of the experimental variables were found to be 0.143 M
SDS and 53% (v/v) methanol. The efficiency of this algorithm was evaluated
by performing the experiment under the predicted optimal conditions. Fig-
ure 4 shows the chromatogram obtained under these conditions. As it can be
observed, good resolutions were achieved for less retained solutes while the
analysis time was lower than 26 min. The experimental and predicted reten-
tion time of target diamines under the optimum conditions are reported in
Table III. It is apparent that a good agreement was achieved between pre-
dicted and experimental values of the retention time (R2 = 0.9999). The av-
erage relative error in prediction of the retention times in the optimal condi-
tions was 0.96%.

Fig. 4. Chromatogram of five aromatic diamines at optimum condition obtained using

eq. (j). Mobile phase: 0.143 M SDS–53% methanol, pH = 3; solute identity and other
chromatographic conditions as Fig. 2

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Evaluation of Some Empirical Retention Models 409

Table III. Predicted and experimental retention times in optimum separation condition

Solutes tR, exp. (min) tR, pred. (min) Relative error (%)
(1) 8.84 8.79 0.57
(2) 9.90 9.85 0.51
(3) 11.07 10.92 1.36
(4) 18.03 17.85 1.00
(5) 25.93 25.57 1.39
Solute: (1) 1,5-naphthalenediamine; (2) 4-(4-aminophenyl) azoaniline;
(3) 1,4-phenylenediamine; (4) 4,4′-diaminobiphenyl; (5) 4,4′-diaminodiphenylmethane.
Conditions as Fig. 4

Separation of Diamines in RPLC and MLC

Figure 5 shows two representative chromatograms of the diamines in RPLC
and MLC modes. As observed, in the hydro-organic mode, extensive peak
tailing occurred. In contrast, in the MLC mode, the peaks were nearly

Fig. 5. Typical chromatogram of five aromatic diamines in (a) RPLC and (b) MLC modes.
Mobile phase: (a) 30% methanol and (b) 0.150 M SDS/30% methanol both at pH = 3;
solute identity and other chromatographic conditions as Fig. 2

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410 M.R. Hadjmohammadi and S.S.S.J. Nazari

symmetrical but poor peak shapes with high band broadening were ob-
tained. Similar peak shapes and behaviors were obtained for other mobile
phase compositions in each RPLC and MLC mode. As can be seen in Figs. 2
and 4, in comparison to RPLC and MLC modes, HSC offers narrower and
more symmetrical peaks, so HSC was considered as suitable RPLC mode
for separation of selected aromatic diamines.

Conclusion
The performance of several hyperbolic and logarithmic empirical retention
models to describe the retentions of target diamines in the investigated HSC
region was evaluated. The results of this study showed that the four para-
metric logarithmic model log k = c0 + c1ϕ + c2 [ M ] + c12 (ϕ[ M ])0.5 was the best
retention model and offers high prediction capability with the mean relative
prediction error lower than 0.5%. It is not in agreement with the previously
reported studies which proposed a quadratic hyperbolic five parametric
mechanistic model for description of retentions in HSC [13, 15]. The method
offers promising possibilities in separation of aromatic amines because of
attractive advantages of HSC in terms of analysis time and peak shape and
non-time-consuming optimization process with high predictive efficiency.

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