Isotope Effects in the Solvolysis of Sterically Hindered Arenesulfonyl Chlorides

Article abstract of DOI:10.1002/kin.20945

Solvent isotope effects in the ethanolysis of sterically hindered arenesulfonyl chlorides ruled out a proton transfer in the rate-determining step and agreed with a S_N2 mechanism involving at least a second solvent molecule in the transition state (TS). The lack of a secondary kinetic isotope effect in the o-alkyl groups allows us to disregard the possible contribution of σ-π hyperconjugation. The measured activation parameters are consistent with a S_N2 mechanism involving the participation of solvent molecules in the TS, possibly forming a cyclic TS through a chain of solvent molecules.

Full text of DOI:10.1002/kin.20945

Isotope Effects in the
Solvolysis of Sterically
Hindered Arenesulfonyl
Chlorides
2
2
1
MYKYTA IAZYKOV,1,2 MOISES CANLE L., J. ARTURO SANTABALLA, LUDMILA RUBLOVA
´
1Department of General Chemistry, Faculty of Ecology and Chemical Technology, Donetsk National Technical University,
83015, Donetsk, Ukraine
2Chemical Reactivity and Photoreactivity Group, Departamento de Qu´ımica F´ısica e Enxen˜arı´a Qu´ımica, Faculty of Sciences
and Center for Advanced Scientific Research (CICA), University of A Corun˜a, E-15071 A, Corun˜a, Spain
Received 22 March 2015; revised 5 August 2015; accepted 7 August 2015
DOI 10.1002/kin.20945
Published online 22 September 2015 in Wiley Online Library (wileyonlinelibrary.com).
ABSTRACT: Solvent isotope effects in the ethanolysis of sterically hindered arenesulfonyl chlo-
rides ruled out a proton transfer in the rate-determining step and agreed with a SN2 mechanism
involving at least a second solvent molecule in the transition state (TS). The lack of a secondary
kinetic isotope effect in the o-alkyl groups allows us to disregard the possible contribution of
σ–π hyperconjugation. The measured activation parameters are consistent with a SN2 mech-
anism involving the participation of solvꢀeCnt molecules in the TS, possibly forming a cyclic TS
through a chain of solvent molecules.
744–750, 2015
2015 Wiley Periodicals, Inc. Int J Chem Kinet 47:
tions on the classical view of the bimolecular substitu-
tion mechanism [4–8,12].
INTRODUCTION
o-Alkyl derivatives of benzenesulfonyl chlorides
show increased reactivity in solvolysis processes
[4–8,12]. In this respect, as shown in Scheme 1, the fea-
sibility of uni- [6] and bimolecular mechanisms [20],
structural modifications of the SN2-type transition state
(TS) involving a second molecule of nucleophile (SN3-
mechanism) [2,21,22], the stabilization of the bimolec-
ular TS by intramolecular interactions, hyperconju-
gation effects [23], or stereochemical rearrangements
during the nucleophilic attack [4,8] have been dis-
cussed.
Despite the existence of a large corpus of research on
solvolytic processes near sulfonyl centers [1–23], de-
tails on the mechanism of this nucleophilic substitution
remain unclear. A number of authors have proposed
SN2 [2–6,9–15] or borderline SN1–SN2 mechanisms
for this process [16–19]. However, sterically hindered
derivatives of aromatic sulfonic acids that contain
o-alkyl groups show kinetic features that pose ques-
Correspondence to: J. Arturo Santaballa; e-mail: arturo@udc.es.
Supporting Information is available in the online issue at
www.wileyonlinelibrary.com.
In addition, the effect of substitution at sterically
hindered sulfonyl center is usually considered a minor
effect, which is not always the case.
ꢀC
2015 Wiley Periodicals, Inc.

SOLVOLYSIS OF STERICALLY HINDERED ARENESULFONYL CHLORIDES
745
Scheme 1 Mechanistic possibilities for solvolytic processes at a sulfonyl center.
Scheme 2 SIE on the ethanolysis of sterically hindered arenesulfonyl chlorides (R1 = Me(2), t-Bu(1)).
Scheme 3 SKIE on the solvolysis of sterically hindered arenesulfonyl chlorides 2 and 2D (R2 = H-, Me-, Et-, Pr-, i-Pr-).
Here, we analyze the mechanism of solvolysis, hy-
drolysis, and alcoholysis of sterically hindered arene-
sulfonyl chlorides in the light of new results of solvent
isotope effects (SIE; Scheme 2) and secondary kinetic
isotope effects (SKIE; Scheme 3) in the temperature
range 303–323 K.
All solvents were thoroughly purified and tested
for the presence of water impurities immediately be-
fore the kinetic experiments [24]. The acceptable water
content was considered <0.002%.
Analytical-grade alcohols were purchased from
Sigma-Aldrich (St. Louis, MO, USA). Molecular
˚
sieves (3 A) were used for dehydration. All alco-
hols were redistilled immediately before the kinetic
experiments at the temperatures specified in the liter-
ature (bpMeOH = 64,4°C; bpEtOH = 78.32°C; bpPrOH
= 97.15°С; bpi-PrOH = 82,6°C at 760 mmHg). Water
obtained from the distiller Auga ELIX-Q was used for
the hydrolysis.
Deuterated ethanol was obtained by the reaction of
sodium ethoxide with pure heavy water. The initial
ethoxide was prepared by dissolving of metal sodium
in ethanol. Furthermore, after the alcohol distilling off,
EXPERIMENTAL
Kinetic runs were spectrophotometrically monitored
under pseudo–first-order conditions with respect to the
nucleophile on a Cary 1E UV–VIS spectrophotome-
ter, in thermostated quartz cuvettes at temperatures be-
tween 303 and 323 K. Examples of UV–VIS spectra
and time-resolved absorbance profiles are shown in the
Supporting Information.
International Journal of Chemical Kinetics DOI 10.1002/kin.20945

746
IAZYKOV ET AL.
Table I SIE Observed in the Ethanolysis of X-ArSO2Cl
X-
T (K)
kEt-OD × 104 (s−1
)
kEt-OH × 104 (s−1
)
SIE = (kEt-OH/kEt-OD
)
(1) 2,6-Ме2–4-tBu-
303
313
323
303
313
323
303
313
323
1.78 0.01
4.00 0.02
8.04 0.05
1.63 0.01
3.57 0.01
7.60 0.04
0.26 0.01
0.66 0.01
1.42 0.01
2.25 0.01
5.70 0.04
11.3 0.1
2.24 0.01
4.99 0.01
10.2 0.1
0.36 0.01
0.82 0.01
1.91 0.01
1.26 0.02
1.42 0.06
1.41 0.06
1.37 0.02
1.40 0.02
1.34 0.02
1.39 0.02
1.24 0.02
1.35 0.02
(2) 2,4,6-Me3-
(3) 4-Me-
the residue was dried under vacuum. Heavy water in
a fourfold excess was added to ethoxide; the reaction
mixture was boiled under reflux (for 30 min) and dis-
tilled with a reflux condenser. Further purification cor-
responds to the methods mentioned previously.
2,4,6-Me3-benzenesulfonyl chloride (2) and 4-Me-
benzenesulfonyl chloride (3) were obtained from
Sigma-Aldrich and recrystallized from hexane prior
to its use.
rate constants and the corresponding SIE are collected
in Table I.
Ortho-methylated substrates show increased reac-
tivity toward solvolysis in all cases (Table I). Change
from protonated to deuterated solvent causes a slight
decrease in the observed solvolytic rate constants.
For compound 3, adopted as a model compound, SIE
ranges between 1.24 and 1.39 (Table I). SIE for hin-
dered substrates 1 and 2 shows a similar range of SIE,
1.26–1.42, in agreement with previous observations
for the methanolysis of sulfonyl chlorides [9,26]. The
observed SIEs are comparable when considering dif-
ferent compounds and temperatures. For the methanol-
ysis of 2 and 3 SIE (kMe-OH/kMe-OD) are, respectively,
1.68 and 1.72, in good agreement with those observed
here [9,26]. Similar SIEs, ranging from 1.2 to 1.6, are
typical for SN2 processes at sulfonyl centers [9,26–29].
These results point to a SKIE of the alcoholic proton,
the proton transfer between the oxygen of the attacking
alcohol and that of a solvent molecule, not taking place
in the rate-determining step.
Deuterated mesitylene sulfonyl chloride (2D) was
synthesized from deuterated mesitylene [mesitylene-
d12 (98 atom%D); Sigma-Aldrich] as follows [25]: The
reaction was carried out under constant stirring at 273
K, 1 mol of NaCl was added to 1 mol of the mesitylene
in 450 mL of an inert solvent (CHCl3, CCl4, hexane);
then 5 mol of chlorosulfonic acid were slowly added
dropwise for half an hour. After 3–4 h, the reaction
mixture was poured onto ice, treated with chloroform;
the extract was dried over Na2SO4 and filtered. The
filtrate was evaporated under vacuum. The resulting
deuterated sulfonyl chloride (2D), the middle fraction,
was collected, and the product recrystallized from hex-
ane with a yield of 80%, mp = 66.5–67°C. As there is
no isotopic exchange, the percentage of deuteration in
2D must be the same as in the parent mesitylene-d12.
2,6-Ме2–4-tBu-benzenesulfonyl chloride (1) was
synthesized analogously from the 1-tert-butyl-3,5-
dimethylbenzene with a yield of 85%; mp = 66–67°C.
The structure and purity of the obtained sulfonyl
compounds were confirmed by NMR spectroscopy and
monocrystal X-ray diffraction (see the Supporting In-
formation).
The analysis of the SIE could be done in terms of
fractionation factors:
kEtoH
φEtOL
ꢀiφi=|
SIE =
=
kEtOD
where φEtOL is the fractionation factor of the al-
coholic hydrogen/deuterium of ethanol, whereas φ╪
is/are the fractionation factor(s) of the alcoholic hy-
drogen/deuterium atom(s) involved in the TS.
The fractionation factor of any hydrogen/deuterium,
which behaves like a hydrogen/deuterium of the sol-
vent, is equal to one, whereas that of the corresponding
lyonium ion is lower than unity, for example, φ(L3O+)
= 0.69 [30] or φ(MeOL2+) = 0.60 [31], where L des-
ignates either H or D. From there, it follows that the
more charge on the hydrogen/deuterium, the lower is
the value of its fractionation factor, i.e. the value of the
RESULTS AND DISCUSSION
The SIE was studied to check the catalytic assistance
of the solvent as a nucleophile in the ethanolysis of
X-ArSO2Cl in the range 303–323 K [2]; the observed
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SOLVOLYSIS OF STERICALLY HINDERED ARENESULFONYL CHLORIDES
747
Scheme 4 “Early” (a) and “late” (b) TSs for the SN2 mechanism of arenesulfonyl chlorides solvolysis with general base
catalysis by a second solvent molecule.
fractionation factor gives information on the amount
of charge on the hydrogen/deuterium relative to the
solvent.
The value of the SIE could be consistent, regard-
less of the position of the hydrogen/deuterium, with
both “early” (Scheme 4a) or “late” (Scheme 4b) SN2
TSs. When the extreme “early” TS is considered, the
hydrogen/deuterium is only starting to be transferred
to another solvent molecule, and assuming the frac-
tionation factor of the alcoholic hydrogen/deuterium
should be similar to that of MeOL2+ (φL+ca. 0.60 rel-
ative to MeOL) [31], a SIE = (kEtOH/kEtOD = 1/0.60)
ca. 1.6 would be expected; in this case, the hydro-
gen/deuterium should resemble that of protonated al-
cohol. Under the same assumption, SIE = (kEtOH/kEtOD
= 1/0.602) ca. 2.8 would be expected for the extreme
“late” TS, where the hydrogen/deuterium has been al-
most fully transferred to another solvent molecule, so
two hydrogens/deuteriums contribute to the SIE.
The observed SIE is ca. 1.35 (Table I), which im-
plies the TS lies in between the “early” and “late” TSs
for the SN2 mechanism described above (Scheme 4),
the product of the fractionation factors of the hydro-
gens/deuteriums involved in the TS being ࣈ0.74. It
could be the value for only one hydrogen/deuterium
(i.e., φ╪L = 0.74) that of the alcohol molecule bonded
to the sulfur atom at the TS, or the product of several
of them somehow participating in the TS; such figure
is compatible even with a cyclic one involving several
solvent molecules as shown in Scheme 5, i.e., 0.74 =
(φL· φL’· φL’’· φL’’’)╪ with (φL< φL’· ࣈ φL’’· ࣈ φL ’’’
ࣘ 1). These results support the participation of, at least,
a second solvent molecule in the TS, through a general-
Scheme 5 TS for the general-base catalyzed SN2 mech-
anism for solvolysis of arenesulfonyl chlorides involving a
chain of solvent. molecules.
base catalysis mechanism [2]. There is strong evidence
in the literature for this kind of mechanism, with par-
ticipation of solvent chains [32–35]. It has been found
that there are an optimal number of solvent molecules
that facilitates the mechanism, for example, via linear
proton transfer in the TS [34].
International Journal of Chemical Kinetics DOI 10.1002/kin.20945

748
IAZYKOV ET AL.
Table II Activation Parameters for X-ArSO2Cl Ethanolysis in EtOH and EtOD
X-
Solvent
ꢁH╪ (kJ·mol−1 a
)
ꢁS╪ (J·mol−1·K−1 a
)
ꢁG╪ (kJ·mol−1 a,b
)
(1) 2,6-Ме2–4-tBu-
Et-OD
Et-OH
Et-OD
Et-OH
Et-OD
Et-OH
59
64
60
57
66
66
2
4
1
3
3
2
–146
–126 14
–143
–150
–137
–137
5
105
104
105
104
109
109
1
9
3
5
6
3
(2) 2,4,6-Me3-
(3) 4-Me-
2
8
9
6
aEstimated considering the second-order constant, i.e., k2 = kobs/[solvent].
bValue calculated at 313 K.
Activation parameters (ꢁH╪, ꢁS╪, and ꢁG╪) are
within statistical error when the solvent is isotopically
modified, i.e. EtOD instead of EtOH (Table II). Steri-
cally hindered substrates 1, 2 show slightly lower ꢁG╪
ꢀ (104–105 kJ·mol−1) in comparison with the less ster-
ically hindered 3 [31,36,37], which provides additional
evidence against proton transfer in the rate-determining
step.
On the other hand, the large negative ꢁS╪ values
are consistent with highly ordered TSs, which support
the participation of solvent molecules in the TS, as is
shown in Scheme 4. The low and similar ꢁH╪ values
Table III Effective Rate Constants and Activation Parameters for Solvolysis of 2 and Deuterated-2 (2D) using
Different Solvents as Nucleophiles
Compound Nucleophile T (K) kobs × 104 (s−1
)
ꢁH╪ (kJ·mol−1 a
)
ꢁS╪ (J·mol−1·K−1 a
)
ꢁG╪ (kJ·mol−1 a,b
)
2
H2O
293
298
303
308
313
318
303
313
318
323
328
303
323
323
293
298
303
308
313
318
303
313
318
323
328
303
323
323
505
8
49
2
–134
7
91
5
746 25
1090 42
1640 57
2000 31
2650 116
2.24 0.01
4.99 0.02
7.06 0.01
10.2 0.1
14.2 0.01
13.2 0.1
6.13 0.02
0.84 0.01
EtOH
57
3
–150
8
104
5
MeOH
PrOH
i-PrOH
H2O
54
59
55
51
4
1
2
2
–148 13
100
105
110
91
8
1
3
–147
–173
–128
2
5
5
2D
493
2
3
764 10
1120 35
1550 27
2140 37
2790 81
2.23 0.01
4.95 0.01
7.59 0.01
10.2 0.01
13.8 0.01
12.5 0.1
5.83 0.01
0.87 0.01
EtOH
59
2
–143
7
104
4
MeOH
PrOH
i-PrOH
–
–
–
–
–
–
–
–
–
aEstimated considering the second-order constant, i.e., k2 = kobs/[solvent].
bValue calculated at 313 K.
International Journal of Chemical Kinetics DOI 10.1002/kin.20945

SOLVOLYSIS OF STERICALLY HINDERED ARENESULFONYL CHLORIDES
749
Table IV SKIE Observed for the Solvolysis of 2 and 2D
with Different Solvents as Nucleophiles between 303
and 323 K
involving at least a second solvent molecule in the
TS. No SKIE is observed when hydrogens of the o-
alkyl groups are replaced by deuteriums, which discard
σ–π hyperconjugation. Activation parameters are sim-
ilar regardless of the steric hindrance of the substrates,
which points to a similar reaction mechanism for all of
them. Large negative ꢁS╪ and low comparable ꢁH╪
are consistent with a SN2 mechanism with participa-
tion of, at least, a second solvent molecule in the TS,
and most possibly with a cyclic TS in which a reduced
number of solvent molecules form chains, in a general-
base catalysis mechanism. The reasons for the “posi-
tive steric effect” of o-alkyl (methyl) groups should be
attributed to structural features of the SN2 transition
state. Further experimental and computational studies
are in progress to clarify this point.
Nucleophile
H2O
T (K)
SKIE (k2/k2D)
293
298
303
308
313
318
303
313
318
323
328
303
323
323
1.03 0.01
0.98 0.01
0.97 0.01
1.06 0.02
0.93 0.02
0.95 0.02
1.00 0.01
1.01 0.01
0.93 0.02
1.00 0.01
1.03 0.01
1.06 0.01
1.05 0.01
0.96 0.02
EtOH
MeOH
PrOH
i-PrOH
Authors gratefully acknowledge EU financial support for the
mobility of MI to the UDC within the trans-European mo-
bility Erasmus Mundus action TEMPO (372283–1–2012–1-
PT-ERA MUNDUS-EMA21).
point to a highly concerted TS, which would support
the hypothesis of formation of solvent chains as in
Scheme 5.
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International Journal of Chemical Kinetics DOI 10.1002/kin.20945