Quantum-chemical study of thermodynamics of hydrogen-bonded methylamine-methanol complexes reaction with dimethyl carbonate

Article abstract of DOI:10.1134/S1070363214080052

Thermodynamic parameters of the reactions of dimethyl carbonate cis-cis and cis-trans conformers with methylamine, methylamine dimer, and methylamine complexes involving linear methanol associates have been computed with the B3LYP and WB97XD quantum-chemi

Full text of DOI:10.1134/S1070363214080052

ISSN 1070-3632, Russian Journal of General Chemistry, 2014, Vol. 84, No. 8, pp. 1480–1486. © Pleiades Publishing, Ltd., 2014.
Original Russian Text © A.Ya. Samuilov, F.B. Balabanova, Ya.D. Samuilov, A.I. Konovalov, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84,
No. 8, pp. 1251–1258.
Quantum-Chemical Study of Thermodynamics
of Hydrogen-Bonded Methylamine–Methanol Complexes
Reaction with Dimethyl Carbonate
A. Ya. Samuilova, F. B. Balabanovaa, Ya. D. Samuilova, and A. I. Konovalovb
a Kazan National Research Technological University, ul. K. Marksa 68, Kazan, Tatarstan, 420015 Russia
e-mail: ysamuilov@yandex.ru
bArbuzov Institute of Organic and Physical Chemistry, Kazan Research Center,
Russian Academy of Sciences, Kazan, Tatarstan, Russia
Received February 20, 2014
Abstract—Thermodynamic parameters of the reactions of dimethyl carbonate cis–cis and cis–trans conformers
with methylamine, methylamine dimer, and methylamine complexes involving linear methanol associates have
been computed with the B3LYP and WB97XD quantum-chemical methods. The both methods have given
similar results. Thermodynamically, reactions of the cis–trans conformer are preferred over the analogous
reactions of the cis–cis conformer, and the reactions with methylamine dimer and methylamine–methanol
trimer complex are preferred over the reactions with methylamine monomer. The acid–base properties of the
hydrogen-bonded methanol complexes are significantly enhanced with increasing degree of association.
Stability of the methylamine complexes with methanol clusters is increased with more of the alcohol molecules
involved.
Keywords: hydrogen-bonded complex, thermodynamics, acidity, basicity, aminolysis
DOI: 10.1134/S1070363214080052
Reactions of dimethyl carbonate with primary
amines have been intensively studied experimentally
[1–6]. Such reactions are interesting because thermal
decomposition of their products, carbamates, allows
for phosgene-free production of isocyanate [7–10].
was not studied. Second, participation of the hydrogen-
bonded forms of the amine, including its complexes
with methanol (the reaction product) in the reaction
was not considered. Furthermore, alcohols are known
to catalyze aminolysis of esters [13–15]. Indeed, the
autocatalysis phenomenon was revealed in reactions of
primary amines with dimethyl carbonate [16]. Thermo-
dynamic parameters of a number of reactions of
hydrogen-bonded complexes much differed from those
in the case of non-associated compounds [17–20].
RNH2 + CH3OCOOCH3 → RNHCOOCH3 + CH3OH,
RNHCOOCH3 → RN=C=O + CH3OH.
This technology does not involve any highly toxic
compounds and meets the requirements of green
chemistry.
In view of the above, the present work aimed to
compare thermodynamic parameters of the reactions of
dimethyl carbonate with methylamine, its hydrogen-
bonded dimer, and its hydrogen-bonded complexes
with methanol.
Choice of the proper reaction conditions requires
knowledge of the reaction thermodynamics. Li et al.
estimated thermodynamic parameters of the aniline
reaction with dimethyl carbonate using the empirical
Benson’s method [11]. Gao et al. studied thermo-
dynamics of ammonia reaction with dimethyl car-
bonate using the PW91 density functional theory
method [12]. In the both studies several important
complications were neglected. First, potentially
different reactivity of dimethyl carbonate conformers
Thermodynamic parameters of conformational
equilibrium of dimethyl carbonate. As shown with
IR spectroscopy [21], X-ray scattering [22], gas-phase
electron diffraction [23], and quantum-chemical
simulation [24, 25], dimethyl carbonate consisted of a
1480

QUANTUM-CHEMICAL STUDY OF THERMODYNAMICS
1481
Table 1. Thermodynamic parameters of dimethyl carbonate
cis–cis → cis–trans transition in the gas phase at 298 K as
computed with the B3LYP and WB97XD methods
Table 2. Ratio of equilibrium constants of the analogous
reactions involving dimethyl carbonate cis–trans and cis–cis
conformers (Kcis–trans/Kcis–cis) as function of temperature
B3LYP/6-
311++G(df,p)
WB97XD/6-
311++G(df,p)
Temperature, K
Simulation
Parameter
method
298
373
423
473
ΔG, kJ/mol
12.5
12.1
–1.2
12.3
15.1
9.3
B3LYP
153
145
57
43
36
24
25
15
ΔH, kJ/mol
ΔS, J K–1 mol–1
WB97XD
mixture of two major conformers: cis–cis and cis–
trans. The cis–trans conformer was found less stable
than the cis–cis form. According to the available
experimental data, fraction of the cis–trans conformer
in the liquid phase was of 1% [21, 22]. Figure 1 shows
geometry parameters of dimethyl carbonate con-
formers, as computed using the B3LYP and WB97XD
methods. Table 1 lists thermodynamic parameters of
the transition of dimethyl carbonate cis–cis conformer
into the cis–trans conformer.
As seen from Table 1, the enthalpy term gave the
major contribution into the difference of the
conformers Gibbs energy, whereas the entropy factor
was of minor importance.
From the above-discussed results it follows that the
reaction of dimethyl carbonate cis–trans conformer is
always thermodynamically preferential over the same
reaction of the cis–cis conformer, provided that their
products are structurally similar.
As seen from Table 2, thermodynamic preference
of the cis–trans conformer reaction over the same
reaction with the cis–cis conformer somewhat
decreased upon heating, remaining fairly large over the
whole studied range of temperature.
The both methods applied gave similar results. The
computed data were in complete agreement with the
experiment and other simulation results, confirming
the higher stability of cis–cis conformer of dimethyl
carbonate. For example, the energy gap between cis–
trans and cis–cis conformers of dimethyl carbonate as
computed in this work was of 12.3–12.5 kJ/mol, its
experimental estimate being of 10.9±2.1 kJ/mol [21].
The energy gap obtained with the MP2 method ranged
from 12.3 to 14.6 kJ/mol depending on the applied
basis [24, 25]. The activation (rotation) barrier of the
cis–cis conformer transformation into the cis–trans one
was of 42 kJ/mol [24]. The rotation entropy being low,
the rate of the cis–cis ҙ cis–trans transformation at
298 K was of about 105 s–1. Hence, the equilibrium
between the conformers of dimethyl carbonate should
be established almost immediately.
Thermodynamics
hydrogen
bonding
of
methylamine to give self-associates and complexes
with linear methanol associates. Amines and
alcohols readily form hydrogen-bonded complexes via
self- and hetero-association in the gas and liquid states
[26–28]. Methylamine can act as proton donor or
proton acceptor to form two types of hydrogen-bonded
complexes with methanol and its linear associates. In
the present work we considered complexes between
methylamine and linear methanol associates with
methylamine acting as proton acceptor.
(a)
(b)
Fig. 1. The Stewart−Briegleb models of dimethyl carbonate (a) cis–trans and (b) cis–cis conformers as obtained with the B3LYP
(WB97XD) simulation. Interatomic distances are given in Å.
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SAMUILOV et al.
We computed thermodynamic parameters of
methylamine dimerization [Eq. (1)], its association
with methanol [Eq. (2)] and with linear methanol
associates [Eqs. (3), (4)].
(1)
(2)
(3)
2CH3NH2
CH3NH
H
II
NH2CH3
I
I + CH3OH
CH3NH2
H
CH3
O
IIIa
IVa
I + O
CH3
IIIb
H
OH
CH3NH2
H
H
O
O
CH3
CH3
CH3
IVb
CH3NH2
I + H
H
O
H
O
H
O
O
H
O
H
O
(4)
CH3
CH3
IIIc
CH3
CH3
CH3
CH3
IVc
Figure 2 shows the Stewart–Briegleb models of the
mentioned complexes and of methyl N-methylc-
arbamate (V) as simulated with the B3LYP and
WB97XD methods. Compound V is shown in the
trans conformation which is most stable in the cases of
carbamates according to simulations presented in [29–
33]. Geometry parameters of the complexes as
simulated with the B3LYP and WB97XD methods
were similar.
thermodynamic basicity and acidity of linear methanol
associates as determined with the B3LYP/6-311++
G(df,p) simulation.
The corresponding experimental parameters were
as follows (monomeric methanol at 298 K): ΔGacid
1571 kJ/mol [41], ΔНacid 1597 kJ/mol [41], gas
basicity (GB) 724 kJ/mol [42], and proton affinity
(PA) 754 kJ/mol [42]. Hence, deviation of the
computed values from the experimental ones was
below 2%. As follows from Table 4, stability of
methanol hydrogen-bonded complexes with linear
methanol associates changed in line with their acidity.
Table 3 lists thermodynamic parameters of reac-
tions 1–4 as derived with the B3LYP and WB97XD
methods.
The acid–base properties of methanol associates
enhanced substantially with increasing number of the
associated alcohol molecules. Hence, transformations
of alcohols in chemical reactions driven by the acid–
base properties always involve alcohol associates.
Thermodynamic parameters of complexes II and
IVa–IVc formation as obtained with the B3LYP and
WB97XD methods were close. The complexes formed
via methylamine dimerization were the least stable.
The corresponding Gibbs energy and enthalpy as
computed with the МР2/aug-cc-pvdz method was of
24.4 and –9.43 kJ/mol, respectively [34], whereas
experimental enthalpy of dimethylamine dimerization
in krypton was of –6.34±0.35 kJ/mol [35]. The
experimental value was well in agreement with by the
B3LYP result, whereas the enthalpies derived from the
MP2 and WB97XD simulations were significantly
overestimated.
Thermodynamic parameters of dimethyl
carbonate reactions with methylamine and its
hydrogen-bonded complexes with linear methanol
associates. We performed quantum-chemical simula-
tion of thermodynamic parameters of cis–cis dimethyl
carbonate model reactions with methylamine [Eq. (5)],
methylamine dimer [Eq. (6)], and methylamine
hydrogen-bonded complexes with linear methanol
associates [Eqs. (7)–(9)], all yielding methyl N-
methylcarbamate (V).
The hydrogen-bonded complexes of methylamine
with linear methanol associates became more stable
with more of methanol molecules in the cluster.
Acidity and basicity of the hydrogen-bonded
complexes were enhanced as compared with those of
monomeric molecules [36–40]. Table 4 lists the
O
CH3
C
H3C
+ I
V + IIIa,
(5)
O
O
VI
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QUANTUM-CHEMICAL STUDY OF THERMODYNAMICS
1483
II
IVa
IVb
IVc
V
Fig. 2. The Stewart–Briegleb models of hydrogen-bonded complexes II and IV and of methyl N-methylcarbamate V as obtained
from the B3LYP (WB97XD) simulation. The bond lengths are given in Å and bond angles are given in deg.
VI + II ҙ V + IVa,
VI + IVa ҙ V + IIIb,
VI + IVb ҙ V + IIIc,
VI + IVc ҙ V + IIId.
(6)
(7)
(8)
(9)
Table 5 lists thermodynamic parameters of reac-
tions (5)–(9) as computed with the B3LYP and
WB97XD methods.
The following correlations were held:
ΔGB3LYP = –1.150 + 1.128ΔGWB97XD (r = 0.982),
ΔHB3LYP = –4.830 + 0.992ΔHWB97XD (r = 0.977).
In Eq. (9), IIId stands for cyclic methanol tetramer.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 8 2014

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SAMUILOV et al.
Table 3. Thermodynamic parameters of reactions (1)–(4) in the gas phase at 298 K
B3LYP
WB97XD
Reaction
ΔG, kJ/mol
–ΔH, kJ/mol
–ΔS, J K–1 mol–1
ΔG, kJ/mol
–ΔH, kJ/mol
–ΔS, J K–1 mol–1
(1)
(2)
(3)
(4)
21.1
6.7
93.2
21.1
14.2
118.8
14.2
7.3
25.7
35.7
52.4
133.9
150.2
143.7
7.8
0.6
28.7
49.2
63.9
122.4
167.3
170.7
–9.5
–13.0
Table 4. Thermodynamic acidity and basicity parameters of linear methanol associates (CH3OH)n in the gas phase at 298 K
(see parameters definition in the text)
n
1
2
3
ΔGacid, kJ/mol ΔНacid, kJ/mol ΔSacid, J K–1 mol–1
GB, kJ/mol
712
РА, kJ/mol
743
–ΔS, J K–1 mol–1
1543
1454
1395
1575
1483
1430
106
97
103
140
120
830
871
119
894
930
Table 5. Thermodynamic parameters of reactions (5)–(9) in the gas phase at 298 K
B3LYP
WB97XD
Reaction
–ΔG, kJ/mol
–ΔH, kJ/mol
–ΔS, J K–1 mol–1
–ΔG, kJ/mol
–ΔH, kJ/mol
–ΔS, J K–1 mol–1
(5)
(6)
(7)
(8)
19.9
14.5
18
15.7
12.8
9.9
33.8
15.3
31.3
8.4
8.5
29.1
11.2
27.2
4.8
6.4
23.1
21.4
12.6
(20.3)а
23.8
3.2
(16.1)
22.7
31.6
(14.1)
3.8
12.2
(17.6)
19.5
–1.9
(9.8)
15.0
47.3
(26.1)
15.2
(9)
a Figures in parentheses refer to formation of cyclic methanol trimer.
Dimethyl carbonate reaction with methylamine
dimer (6) was thermodynamically the most favorable
over the entire temperature range.
In the both cases, the slope coefficient was close to
unity. However, the WB97XD method produced
systematically overestimated Gibbs energy and
enthalpy of the studied reactions as compared to the
B3LYP method.
Enthalpies of reactions (5)–(9) were different (cf.
Table 5) and therefore revealed different temperature
dependences of the equilibrium constants (Fig. 3). The
equilibrium constants shown in Fig. 3 were calculated
using the B3LYP-derived parameters at 298–473 K.
As seen from the plots, in all the studied cases the
equilibrium constant decreased with increasing
temperature.
Thermodynamically, dimethyl carbonate reactions
with methylamine complexes involving monomeric
[Eq. (7)] and dimeric [Eq. (8)] methanol yielding linear
methanol trimer were less favorable than the reaction
with methylamine monomer [Eq. (5)]. However, if
cyclic methanol trimer was considered the reaction
product, equilibrium constants of reactions (5) and (8)
turned almost equal.
Dimethyl carbonate reaction with methylamine
associated with linear methanol trimer yielding
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QUANTUM-CHEMICAL STUDY OF THERMODYNAMICS
1485
potential energy minimum was confirmed by
computation of real vibration frequencies at the same
level of theory.
log K
The standard enthalpy and the Gibbs energy of
formation in the gas phase (298.15 K, 1 atm) were
computed using the corresponding thermal corrections
to the electron energy.
8a
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