RAPID COMMUNICATIONS IN MASS SPECTROMETRY

Rapid Commun. Mass Spectrom. 2010; 24: 3419–3424

Published online in Wiley Online Library (wileyonlinelibrary.com) DOI: 10.1002/rcm.4789

Rapid monitoring of sulfur mustard degradation in

solution by headspace solid-phase microextraction
sampling and gas chromatography mass spectrometry
Jo-Anne M. Creek, Andrew M. McAnoy* and Craig S. Brinkworth
Human Protection and Performance Division, Defence Science and Technology Organisation, 506 Lorimer St, Fishermans Bend,
Victoria 3207, Australia
Received 19 August 2010; Revised 15 September 2010; Accepted 15 September 2010

A method using headspace solid-phase microextraction (HS-SPME) followed by gas chromatog-

raphy/mass spectrometry (GC/MS) analysis has been developed to gain insight into the degradation
of the chemical warfare agent sulfur mustard in solution. Specifically, the described approach
simplifies the sample preparation for GC/MS analysis to provide a rapid determination of changes
in sulfur mustard abundance. These results were found to be consistent with those obtained using
liquid-liquid extraction (LLE) GC/MS. The utility of the described approach was further demon-
strated by the investigation of the degradation process in a complex matrix with surfactant added to
assist solvation of sulfur mustard. A more rapid reduction in sulfur mustard abundance was observed
using the HS-SPME approach with surfactant present and was similar to results from LLE exper-
iments. Significantly, this study demonstrates that HS-SPME can simplify the sample preparation for
GC/MS analysis to monitor changes in sulfur mustard abundance in solution more rapidly, and with
less solvent and reagent usage than LLE. Copyright # 2010 Commonwealth of Australia. Published
by John Wiley & Sons, Ltd.

The threat of a chemical warfare agent (CWA) release in a
civilian environment by a terrorist group, such as the 1995
nerve agent attack in a Tokyo subway system,1 has long
provided interest in CWA reactive chemistries and deconta-
mination methods.2–6 The chemical warfare agent bis(2-
chloroethyl) sulfide, commonly known as sulfur mustard,
is a vesicant that causes chemical burns on skin and is an eye
and lung irritant.7–9 The melting point of sulfur mustard
is 13–148C and, with a vapour pressure of 0.11mm Hg, this
toxic chemical poses both a contact and vapour hazard.2
It also has significant persistence in the environment that
can result in injuries days to weeks after the initial release.
The persistence of sulfur mustard can be significantly
extended when it is left undisturbed in soil or underwater
by the formation of sulfonium ion aggregates that can form
a protective coating on the agent surface.9
Sulfur mustard degrades by either hydrolysis or oxidation
(Scheme 1) and, similar to other CWAs, remediation
historically utilised chlorine-based decontaminants.3 The
hypochlorite ion reacts with sulfur mustard to yield the
corresponding sulfoxide (non-irritant) that can undergo a
second oxidation process to yield the sulfone (vesicant).
Further, elimination reactions of the sulfoxide and sulfone
yield corresponding vinyl analogues of moderate skin
irritancy, and therefore a large excess of hypochlorite is
*Correspondence to: A. M. McAnoy, Human Protection and Per-
formance Division, Defence Science and Technology Organis-
ation, 506 Lorimer St, Fishermans Bend, Victoria 3207, Australia.
E-mail: andrew.mcanoy@dsto.defence.gov.au
required to render sulfur-mustard-contaminated areas safe.2
Interestingly, degradation of sulfur mustard by hydrolysis
occurs rapidly when the agent is diluted in a large excess
of water yielding the relatively non-toxic product bis
(2-hydroxyethyl) sulfide, otherwise known as thiodiglycol.9
However, the solubility of sulfur mustard in water is
extremely low resulting in the formation of sulfonium ion
aggregates at the agent/water interface as the major products
of hydrolysis when larger amounts of the agent are present.
As a result many decontaminant formulations contain
surfactants and co-solvents providing an additional degree
of complexity to the analysis.
Headspace solid-phase microextraction (HS-SPME) is a
well-established technique for the analysis of volatile
compounds and is typically coupled with gas chromatog-
raphy/mass spectrometry (GC/MS) to determine trace
amounts of analyte.10 HS-SPME methods concentrate
volatile compounds onto a fibre removing the need for
time-consuming sample preparation steps and they are
particularly amenable to the rapid and safe analysis of
hazardous chemicals;11 for example, the detection and
identification of CWAs using field portable GC/MS
systems.12–14 HS-SPME approaches have also been used to
investigate nerve agent and sulfur mustard contamination
in soil.15,16 More recently, D’Agostino et al. combined HS-
SPME sampling with desorption electrospray ionisation
(DESI)-MS for the rapid analysis of CWAs.17,18 Can HS-
SPME be used to rapidly monitor changes in sulfur mustard
abundance during its degradation? Sulfur mustard has been

Copyright # 2010 Commonwealth of Australia. Published by John Wiley & Sons, Ltd.
3420 J. M. Creek, A. M. McAnoy and C. S. Brinkworth
Scheme 1. Degradation of sulfur mustard by either hydroly-
sis or oxidation.
detected in the headspace above aqueous samples using
adsorbent tubes, with relatively long sampling times,
followed by GC/MS analysis.19,20 Here we investigate the
use of a relatively simple HS-SPME GC/MS approach to gain
insight into the degradation of sulfur mustard in solution by
monitoring its decreasing abundance in close to real time.
EXPERIMENTAL
Polydimethylsiloxane/divinylbenzene (PDMS/DVB, 65 mm)
SPME fibres and a manual fibre holder were obtained from
Supelco (Bellefonte, PA, USA). Ethanol, acetonitrile and N-
tert-butyldimethylsilyl-N-methyl trifluoroacetamide were
obtained from Sigma-Aldrich (Castle Hill, NSW, Australia)
and detergent (Palmolive) was obtained from a local
supermarket. Sulfur mustard was obtained and used in
accordance with local and international regulations. CAU-
TION: Sulfur mustard is a highly toxic vesicant and should
only be handled under controlled conditions in approved
laboratories.
GC/MS analysis of SPME fibres
A known amount of sulfur mustard was added to a reaction
vial (40 mL) from a standard solution in dichloromethane
and the solvent was allowed to evaporate. The vial was
sealed with a screw cap septum and equilibrated for 20 min
before exposure of the pre-conditioned SPME fibre to the
headspace for 30 s. Analysis of the SPME fibre was
performed on a GC/MS system (Agilent 6890 GC, 5973
MS, Foster City, CA, USA) fitted with a reduced volume
SPME inlet liner with a Merlin micro-seal. The SPME fibre
was inserted into the inlet and exposed to an injector
temperature of 2508C to rapidly desorb the sample and
recondition the fibre between sampling. A 1:10 split of the
vaporised sample was loaded onto a capillary column
Copyright # 2010 Commonwealth of Australia. Published by John Wiley & Sons, Ltd.
(Agilent HP-5MS, 30 m
250 mm, 0.25 mm i.d.). The carrier
gas used was helium at a flow rate of 1.1 mL/min. The oven
temperature was set at 2508C and the GC experiment was run
isothermally. The mass spectrometer was operated under
standard electron ionisation (EI) conditions (70 eV) scanning
the range m/z 50–400 for a total run time of 3 min. The EI mass
spectrum of each detected compound was compared with a
library spectrum to confirm its identity. All peak areas were
obtained by integration of the m/z 109 ion of sulfur mustard
in the extracted ion chromatogram.
HS-SPME-monitored reactions
HS-SPME monitoring experiments were conducted in a
screw-capped vial with septum (40 mL) containing an
aqueous mixture (10 mL) of water and ethanol as a co-
solvent (30% total concentration by volume). As with
previous studies into the hydrolysis of sulfur mustard and
related 2-chloroethyl sulfides, a co-solvent was necessary
due to the low solubility of the substrate in water.21–23 The
vial was sealed and the temperature of the stirred reaction
mixture equilibrated to 258C for 30 min. Sulfur mustard
(10 mL) was then added via a gas-tight syringe and the
headspace above the reaction mixture sampled by exposing
a SPME fibre to the headspace for a set sampling time of 30 s
and then immediately analysed by GC/MS as described
above. A manual fibre holder fitted with a spacer was used
to ensure that the fibre sample depth and position were
consistent for each sampling process. HS-SPME experiments
conducted with surfactant present in the reaction mixture
involved the addition of a commercial dishwashing liquid
(100 mL) to the initial aqueous mixture.
LLE-monitored reactions
Liquid-liquid extraction (LLE) experiments were conducted
in a screw-capped vial with septum (40 mL) containing an
aqueous mixture (10 mL) of water and ethanol as a co-solvent
(30% total concentration by volume). Sulfur mustard (10 mL)
was added and the capped vial was stirred at a constant
rate. After a set time the vial was then quenched by extracting
with dichloromethane (10 mL). The organic layer was
removed, dried (MgSO4) and filtered using a 0.45 mm PTFE
syringe filter. The extract was diluted in dichloromethane
and analysed by GC/MS to determine the relative abun-
dance of sulfur mustard. The aqueous layer was dried under
nitrogen with any hydrolysis products derivatised by
tert-butyldimethylsilylation (TBDMS) and diluted in dichlor-
omethane prior to GC/MS analysis.24,25 The sample injection
volume used for GC analysis was 1 mL and the instrument
was operated in splitless mode with the following tempera-
ture profile: 0–2 min, 408C; 2–12.4 min, 258C/min ramp and
12.5–17.4 min 3008C. All the remaining GC/MS instrument
settings were implemented as above.
RESULTS AND DISCUSSION
Decontamination products for chemical warfare agents and
other toxic materials continue to be developed in line with
technological advances and user requirements. Analytical
methods used to determine the effectiveness and limitations
of such products need to be rapid and robust. The LLE
Rapid Commun. Mass Spectrom. 2010; 24: 3419–3424
DOI: 10.1002/rcm
 HS-SPME GC/MS monitoring of sulfur mustard in solution 3421

approach for sample preparation of toxic compounds before,

during and following degradation reactions is laborious,
particularly where surfactants are employed to assist
solvation. Alternative sample preparation approaches that
can more rapidly provide insight into degradation processes
would be of significant benefit. As a solventless technique,
HS-SPME is of particular interest in simplifying both the
sample preparation and the analysis of sulfur mustard in
solution.

Sampling optimisation
The extraction of an analyte from the headspace above an
aqueous sample onto a SPME fibre is dependent on a number Figure 1. Typical GC/MS total ion chromatogram for the
of factors including stirring, temperature, sample matrix, HS-SPME GC/MS analysis of sulfur mustard during its hydro-
fibre exposure time and technique. As we aim to monitor the lysis in solution. Inset: EI mass spectrum of sulfur mustard.
degradation reaction of sulfur mustard in near real-time the
fibre exposure time should be relatively short and the sample HS-SPME reaction monitoring
loading reproducible. Analyte extraction at relatively short The relative abundance of sulfur mustard during hydrolysis
fibre exposures occur at pre-equilibrium and so small changes was monitored by HS-SPME GC/MS. A sealed reaction vial
in the length of exposure may lead to large differences in the with septum containing water and ethanol, as a co-solvent
amount of analyte adsorbed onto the fibre. However, Ouyang (30%), was allowed to equilibrate at 258C for 30 min. Sulfur
et al. recently reported sampling times as low as 5 and 10 s for mustard was then added to the stirred mixture and the
the quantification of rapid on-site air sampling by SPME, reaction monitored by HS-SPME GC/MS for 2 h. This
demonstrating that short sampling times are viable.26 involved exposure of a SPME fibre to the headspace above
Initial experiments were conducted to sample the steady- the reaction mixture for a set exposure time at 5 min intervals
state headspace above sulfur mustard in a sealed vial to for the first 20 min and then every 10 min thereafter. After
determine the overall reproducibility of the sampling each sampling, the SPME fibre was immediately analysed by
technique at a relatively short exposure time of 30 s. The GC/MS (Fig. 1). The HS-SPME GC/MS results show a steady
temperature was maintained at 258C and sampling utilised a reduction in sulfur mustard abundance under the reaction
manual SPME fibre holder fitted with a spacer to ensure that conditions with reasonable standard deviations for each time
the fibre sample depth and position were consistent. In point (Table 2). However, an initial increase in sulfur
addition to sampling time, the GC/MS analysis time also mustard abundance was observed from 5 to 10 min, 86% and
needed to be rapid to allow for more time points to be 100% respectively, followed by stabilisation of the sulfur
collected for each reaction. Therefore, the GC injector and mustard measured in the headspace. This occurred as the
oven were set to 2508C and each analysis was run altered system established equilibrium between the solvent
isothermally for 3 min. The isothermal GC/MS method and headspace concentrations of sulfur mustard and
benefited from the relatively clean background of the HS- appeared to take 15–20 min. Subsequent HS-SPME measure-
SPME sample and removed the need to re-equilibrate the ments demonstrate a first-order rate of decrease in sulfur
oven temperature prior to each analysis. mustard abundance with a rate constant and half-life of
The peak area in the extracted ion chromatogram of the
characteristic EI-MS fragment ion at m/z 109 (base peak)
Table 2. HS-SPME GC/MS results for the degradation of
corresponds to the amount of sulfur mustard adsorbed onto
sulfur mustard in aqueous solution (10 mL) containing a co-
a SPME fibre and, in turn, its relative abundance in the
solvent (ethanol, 30%)
headspace. The peak areas obtained following exposure of a
SPME fibre to the steady-state headspace above varying Standard
amounts of sulfur mustard demonstrate reasonable standard Time Average peak Normalised deviation
(min) area (
107) abundance (%) (%, n ¼ 3)
deviations of 3.0–6.7% (Table 1). The results also indicate a linear
response between the observed peak area and the amount of 5 2.10 86.3 13.1
sulfur mustard present. Therefore, we adopted this combined 10 2.43 100.0 5.4
30 s SPME sampling and isothermal GC/MS method for the 15 2.42 99.7 3.7
20 2.40 98.8 2.9
analysis of sulfur mustard degradation that would allow for the 30 2.22 91.4 5.1
rapid monitoring at intervals less than 5 min. 40 1.97 81.1 4.1
50 1.69 69.4 3.2
Table 1. Average peak areas and standard deviations 60 1.49 61.1 1.3
70 1.29 52.9 0.3
observed for exposure of a SPME fibre to the headspace
80 1.06 43.6 9.0
above various amounts of sulfur mustard 90 0.91 37.3 7.6
Sulfur mustard (mg) 1.1 2.2 3.3 4.4 100 0.81 33.5 6.5
Average peak area (
107) 0.50 1.12 1.53 1.93 110 0.63 25.8 13.5
Standard deviation (%, n ¼ 3) 3.0 6.7 6.1 5.1 120 0.49 20.1 12.7

Copyright # 2010 Commonwealth of Australia. Published by John Wiley & Sons, Ltd. Rapid Commun. Mass Spectrom. 2010; 24: 3419–3424
DOI: 10.1002/rcm
3422 J. M. Creek, A. M. McAnoy and C. S. Brinkworth
2.57
104 s1 and 45 min, respectively. This compares with
the rate constants of 1.64
103 s1 and 0.99
103 s1 in
27% and 36% ethanol previously reported.21 However, the
previous study investigated the hydrolysis reaction at
substantially lower concentrations of the sulfur mustard,
which was also pre-dissolved in ethanol, and so it is not
unexpected that the HS-SPME results indicate a lower rate
for the disappearance of sulfur mustard.
LLE GC/MS approach
A number of comparative LLE GC/MS experiments were
conducted to determine the relative amount of sulfur
mustard present in the aqueous mixture at selected points
over the 2 h reaction. Previous similar studies in our
laboratory involved the LLE, sample preparation and
analysis of aliquots taken from larger reaction volumes;
however, inherent sampling difficulties often resulted in
significant experimental errors. Therefore, we adopted the
approach of quenching the reaction at set time points, with
subsequent sample preparation, for analysis by GC/MS.
This also allowed the same reaction conditions to be used as
above except that, rather than sampling the headspace by
SPME, the total remaining sulfur mustard was extracted into
dichloromethane and its relative abundance determined by
GC/MS. In addition, this LLE approach allows degradation
products residing in the aqueous phase to be derivatised for
GC/MS analysis. In the current study, the final product of
sulfur mustard hydrolysis, thiodiglycol (Scheme 1), was
identified as its TBDMS derivative. Further, no oxidation
products were observed in either the organic or the aqueous
phases, indicating that hydrolysis is the only degradation
process occurring under the reaction conditions (Fig. 2).
Figure 2. GC/MS total ion chromatograms of samples pre-
pared from the (a) organic and (b) aqueous phases following
LLE after a reaction time of 60 min. The abundance of sulfur
mustard (peak area, 5.54
106) and the thiodigylcol deriva-
tive (peak area, 9.40
106) indicates the extent of hydrolysis
(63%).
Copyright # 2010 Commonwealth of Australia. Published by John Wiley & Sons, Ltd.
Table 3. Liquid-liquid extraction results for the degradation of
sulfur mustard in aqueous solution (10 mL) containing a co-
solvent (ethanol, 30%)
Standard
Time Average peak Normalised deviation
(min) area (
107) abundance (%) (%, n ¼ 3)
0 2.71 100.0 7.3
30 1.59 58.8 6.8
60 1.02 37.5 4.6
90 0.61 22.5 9.6
120 0.42 15.6 11.9

Average peak area for sulfur mustard standard (63.5 ng/mL) is
2.80
107.
The extraction efficiency of sulfur mustard, based on results
of the 0 min extraction and a standard of known concen-
tration, was determined to be 97%. GC/MS analysis of the
organic extracts show a first-order rate of decrease in sulfur
mustard abundance (Table 3) similar to that observed by HS-
SPME. Specifically, the rate constant and half-life for the
disappearance of sulfur mustard were determined to be
2.67
104 s1 and 43 min, respectively, and these values
compare favourably with the HS-SPME values. A major
disadvantage of the LLE method is that an individual
experiment only provides data for one reaction time point
and so it is significantly more laborious than HS-SPME-GC/
MS. These results indicate that HS-SPME GC/MS can more
rapidly provide similar results to the LLE method for
monitoring sulfur mustard abundance during its hydrolysis
in solution.
Comparison of HS-SPME and LLE approaches
for complex systems
In addition to co-solvents, surfactants are often incorporated
into decontaminant formulations to assist the physical
removal and chemical degradation of CWAs. Therefore,
the utility of the HS-SPME GC/MS approach was investi-
gated by monitoring the degradation of sulfur mustard in a
solution containing a surfactant. Experiments were set up as
above with the exception that a common household
detergent was added to the aqueous mixture. Sulfur mustard
was added to the stirred mixture and the reaction monitored
by HS-SPME GC/MS for 2 h. As above, an initial increase in
sulfur mustard abundance was observed, as the reactant
dissolved into solution and partitioned into the headspace,
followed by an exponential decrease in the abundance
of sulfur mustard (Table 4). Interestingly, the HS-SPME
GC/MS results indicate a significantly more rapid reduction
in sulfur mustard abundance with surfactant present
compared with the above results. For example, the half-life
of sulfur mustard was determined to be 22 min with
surfactant compared with 45 min in the absence of surfactant.
The use of surfactants in decontaminant formulations
assists solubilisation of sulfur mustard, allowing its physical
removal from surfaces and subsequent degradation. In
addition, some surfactant systems have been observed to
enhance the degradation of organophosphorus pesticides
due to relative concentration effects resulting from incorp-
oration of the reactants into the micellar phase.27 Similarly, a
micro-emulsion system has recently been described that
Rapid Commun. Mass Spectrom. 2010; 24: 3419–3424
DOI: 10.1002/rcm
 HS-SPME GC/MS monitoring of sulfur mustard in solution 3423

Table 4. HS-SPME GC/MS results for the degradation of Table 6. Rates of sulfur mustard disappearance obtained
sulfur mustard in aqueous solution containing a co-solvent from HS-SPME and LLE results
(ethanol, 30%) and surfactant (1%) HS-SPME LLE
Standard
Time Average peak Normalised deviation half-life rate constant half-life rate constant
(min) area (
107) abundance (%) (%, n ¼ 3) (min) (
104 s1) (min) (
104 s1)

5 2.39 87.6 15.5 no surfactant 45 2.57 43 2.67

10 2.61 95.9 7.9 surfactant 22 5.21 28 4.10
15 2.73 100.0 5.7
20 2.68 98.2 0.5
30 2.24 82.0 3.0 determined to be 28 min. The analogous half-life obtained
40 1.78 65.2 2.8 from HS-SPME results is lower (23 min) and may be
50 1.33 48.9 3.9
indicative of encapsulation. However, the more significant
60 1.00 36.7 6.9
70 0.71 26.2 4.6 trend from both HS-SPME and LLE results, summarised
80 0.52 18.9 4.7 in Table 6, indicates an enhancement of sulfur mustard
90 0.34 12.4 7.8 degradation under the reaction conditions with surfactant
100 0.25 9.0 6.3 present to assist solvation.
110 0.16 6.0 7.0
120 0.13 4.6 4.0
CONCLUSIONS
co-localises sulfur mustard with an oxidation catalyst to The monitoring of sulfur mustard abundance during its
enhance the degradation process.28 However, the micellar degradation in aqueous solution has been demonstrated
encapsulation of analytes can also be exploited to inhibit the using LLE and HS-SPME methods followed by GC/MS. The
chemical degradation process as reported for the protection LLE method involved quenching the degradation reaction by
of citral (3,7-dimethyl-2,6-octadienal) against oxidation in extraction into dichloromethane and subsequent sample
beverage formulations.29 In our study, encapsulation would preparation for GC/MS. The HS-SPME method involved
result in the removal of sulfur mustard from the bulk periodic sampling of the reaction headspace and was
solution resulting in a reduced amount available to partition significantly less laborious allowing for the near real-time
into the headspace. Therefore, both surfactant-enhanced analysis of up to 12 samples per hour. In addition, a more
degradation and micellar encapsulation of sulfur mustard rapid reduction in sulfur mustard abundance upon addition
may explain the observed HS-SPME results. In principle, of surfactants to the reaction mixture was observed using HS-
the LLE approach would extract the total remaining sulfur SPME, demonstrating the potential of the method as a rapid
mustard present in the bulk solution and/or micelles and screening tool for aqueous decontaminant formulations. In
so this approach was used to gain insight into the HS-SPME comparison with the alternative LLE approach, HS-SPME
results. was found to significantly simplify the sample preparation
A number of comparative LLE experiments were con- for GC/MS analysis for the more rapid monitoring of sulfur
ducted with detergent added as above and the reaction mustard hydrolysis with less solvent and reagent usage.
stopped at 0, 30, 60, 90 and 120 min by the extraction of
the sulfur mustard into dichloromethane. Here the efficiency
of the LLE approach was determined to be 99% based on Acknowledgements
GC/MS results of the 0 min extraction and a standard of The authors would like to thank Alex Theo, Ian Tilley and
known concentration (Table 5). As above, thiodiglycol was Harry Rose (DSTO) for technical assistance and helpful
the only product observed, indicating that hydrolysis is the discussions.
degradation process occurring under the reaction conditions.
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