Molecular complexes of 1,3,5-trinitrobenzene with naphthalene and its derivatives

Article abstract of DOI:10.1134/S1070363209110139

The relation between spectral parameters of molecular complexes formed by 1,3,5-trinitrobenzene with naphthalene derivatives and ionization potentials of the donor molecule is discussed. The molecular complexes were divided into three groups: naphthalene, naphthalene-1-amine, and naphthalene-2-amine derivatives. This division was substantiated in terms of the existence of several intermolecular interactions between the components and steric structure of the complexes. Problems related to classification of molecular complexes are discussed.

Full text of DOI:10.1134/S1070363209110139

ISSN 1070-3632, Russian Journal of General Chemistry, 2009, Vol. 79, No. 11, pp. 2359–2366. © Pleiades Publishing, Ltd., 2009.
Original Russian Text © B.S. Pryalkin, 2009, published in Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 11, pp. 1837–1844.
Molecular Complexes of 1,3,5-Trinitrobenzene with Naphthalene
and Its Derivatives
B. S. Pryalkin
Tomsk State University, pr. Lenina 36, Rossiya, Tomsk, 634050 Russia
Received March 16, 2009
Abstract—The relation between spectral parameters of molecular complexes formed by 1,3,5-trinitrobenzene
with naphthalene derivatives and ionization potentials of the donor molecule is discussed. The molecular
complexes were divided into three groups: naphthalene, naphthalene-1-amine, and naphthalene-2-amine
derivatives. This division was substantiated in terms of the existence of several intermolecular interactions
between the components and steric structure of the complexes. Problems related to classification of molecular
complexes are discussed.
DOI: 10.1134/S1070363209110139
The energies of charge-transfer bands (hν) of
molecular complexes are related to ionization
potentials (IP) of the donor components through first-
order equation (1) [1] or hyperbolic dependence (2)
[2]:
supramolecular structures [8, 9] were classed with a
different form of organization of matter (non-chemical)
[8]; obviously, their classification should require
principles that are different from those underlying
classification of organic compounds.
hν = a IP + b;
(1)
(2)
The present work was aimed at analyzing linear
relation (1) for molecular complexes of 1,3,5-
trinitrobenzene with naphthalene and its derivatives
(π–π complexes according to Mulliken [1]) and
studying the effect of the structure of the components,
intermolecular conformation (structure of complexes),
and ionization potential on the coefficients a and b in
Eq. (1).
hν = IP – S1 + S2/(IP – S1).
Here, a, b, S1, and S2 are empirical parameters.
Equations (1) and (2) reflect dependences between a
property (hν) of a complex system (molecular
complex) and a property (IP) of its component (donor
molecule). Therefore, analysis of these equations for a
large number of complexes formed by a single
acceptor could reveal other factors affecting the above
property of the complexes. Such factors may include
the structure of molecular complex, for properties of a
complex system reflect its composition and structure.
The use of Eqs. (1) and (2) to elucidate the structure of
molecular complexes seems to be quite promising,
taking into account that maxima of charge-transfer
bands of molecular complexes are among the most
reliable parameters which could be determined directly
[3].
The positions of maxima of charge-transfer bands
(both reported previously and measured in the present
work) of molecular complexes formed by 1,3,5-
trinitrobenzene with naphthalene and its derivatives in
chloroform solution, as well as ionization potentials of
the corresponding donor molecules, are collected in
Table 1. In keeping with numerous published data, the
examined complexes have 1:1 composition.
The correlation and regression analysis of Eq. (1)
was performed for all complexes and their particular
groups (Table 1) with respect to both adiabatic and
vertical ionization potentials of donor molecules (Table 2).
Regardless of the type of ionization potential in the
right side of Eq. (1), parameters of the overall linear
equation (1) were unsatisfactory. Therefore, the
examined complexes were divided into several groups,
It was repeatedly noted [1, 3–7] that a set of
molecular complexes derived from the same acceptor
and a number of donors may be described by a single
equation like (1) or (2) only for limited series;
however, factors governing the division into narrow
series were not defined. Molecular complexes or
2359

2360
PRYALKIN
Table 1. Maxima of charge-transfer bands in the electronic absorption spectra of molecular complexes of 1,3,5-trinitro-
benzene and ionization potentials of aromatic donors
Ionization potential of donor moleculea
Maximum of
charge-transfer band, nm
[10–13], eV
Donor
adiabatic
vertical
Naphthalene group π(au)–π
Naphthalene
365 [14]
366 [15]
385 [15]
390 [14]
378 [15]
385 [14]
395 [16]
422b
8.12
7.96
7.96
8.13
8.01
8.01
1-Methylnaphthalene
2-Methylnaphthalene
2-Ethylnaphthalene
Acenaphthene
1,5-Dimethylnaphthalene
1,8-Dimethylnaphthalene
2,3-Dimethylnaphthalene
2,6-Dimethylnaphthalene
2,6-Dipropoksinaphthalene
N,N,N′,N′-Tetramethylnaphthalene-1,8-diamine
1,3-Dimethyl-2,3-dihydroperimidine
2,9,18,25-Tetraoxa-[8,8]-(2,6)-naphthalenophane
Naphthalene-1-amine group
Naphthalene-1-amine
7.85
7.73
7.85
7.82
7.85
7.64 [17]
7.89
7.78
–
7.47d
6.90
–
400[15]
409.8b
(7.86)
(7.80)
(7.95)
(7.90)
(7.57)
7.38d
6.40
386 [15]
393 [15]
452 [18]
500c [19]
575c [19]
464 [18]
(7.51)
455d [20]
460 [15]
464 [14]
465b
7.30
7.91
N,N-Dimethylnaphthalene-1,8-diamine
N-Methylnaphthalene-1,8-diamine
Naphthalene-1,8-diamine
Naphthalene-1-ol
575 [19]
560 [19]
530 [19]
425b
(6.29)
(6.40)
6.65d
7.78
–
–
7.10
7.78
–
Isoquinolin-5-amine
334 [21]
(9.33)
Naphthalene-2-amine group
Naphthalene-2-amine
444 [14]
446 [20]
449 [15]
450 [22]
408b
7.25
7.76
7.40
7.44
7.00
7.60
7.90
7.72
7.87
7.50
Naphthalene-2-ol
Other naphthalene derivatives
1-Methoxynaphthalene
2-Methoxynaphthalene
369b
381b
N,N-Dimethylnaphthalene-1-amine
448 [15]
a
The ionization potentials of donors were taken from [10–13] unless otherwise stated. The value calculated in the present work using
linear correlation (1) is given in parentheses. The adiabatic ionization potential of N,N-dimethylnaphthalene-1,8-diamine was calculated
b
c
using hyperbolic correlation (2).
Data of the present work. The value was not included in correlation analysis of Eq. (1); for
comments, see text. It was used for the calculation of overall linear dependence (1) and hyperbolic dependence (2). d The value was not
included in correlation analysis of Eq. (1) due to strong deviation from the data obtained by other authors; otherwise, the correlation
parameters of linear relation (1) were considerably impaired. e Second ionization potential [23]; for comments, see text.
including naphthalene π(au)–π complexes, naphthalene-
1-amine complexes, and naphthalene-2-amine com-
plexes. The parameters of linear Eq. (1) for particular
groups of complexes were unsatisfactory if vertical
ionization potentials of the donors were involved.
Good correlations were observed when adiabatic
ionization potentials were used. The groups are named
by the name of the parent aromatic system (which is
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MOLECULAR COMPLEXES OF 1,3,5-TRINITROBENZENE
2361
Table 2. Correlation parameters of Eq. (1) for molecular complexes of 1,3,5-trinitrobenzene
Naphthalene group
Parameter
IP typea
All complexes
Naphthalene-1-amine Naphthalene-2-amine
π(au)–π
Linear dependence
Coefficient a
a
v
а
v
а
v
а
v
а
v
а
v
а
v
0.653
0.924
0.00703
0.0180
–1.973
–4.229
0.396
1.083
0.8619
0.8153
0.0317
0.0378
23
1.234
1.027
0.512
0.452
0.000266
0.0463
–1.065
–0.835
0.0141
2.764
0.999
0.772
0.000172
0.0230
5
0.523
0.889
2
Sa
0.00352
0.00140
0.00405
–1.018
–3.982
0.0759
0.238
0.00770
–6.599
–4.968
–0.220
0.472
–0.992
0.959
0.00145
0.0104
9
Coefficient b
2
Sb
Correlation coefficient r
Dispersion S2
0.992
0.992
0.000292
0.000292
5
Sample volume n
26
14
5
5
Hyperbolic dependence
Coefficient S1
S2(C1)
а
а
а
а
а
а
–
–
–
–
–
–
5.140
0.049
1.064
0.178
0.07766
10
–
–
–
–
–
–
–
–
–
–
–
–
Coefficient S2
S2(C2)
Dispersion S2
Sample volume n
a
“a” and “v” refer to adiabatic and vertical ionization potential, respectively.
the same for all donors in a particular group) with
indication of the type of interacting orbitals of the
acceptor and donor. Adiabatic ionization potentials of
donor molecules (Table 1) were calculated using the
obtained correlations (Table 2) and positions of charge-
transfer bands in the electronic absorption spectra of
some complexes. The calculated ionization potentials
of donors were not involved in correlation analysis of
Eqs. (1) and (2).
with respect to the donor molecule. The first group of
complexes also contained the complex derived from
N,N,N′,N′-tetramethylnaphthalene-1,8-diamine. According
to the data of photoelectron spectroscopy and
quantum-chemical calculations [23], the first
ionization potential of N,N,N′,N′-tetramethylnaphtha-
lene-1,8-diamine (IPa = 6.45 eV) corresponds to
electron abstraction from the lone electron pair on the
nitrogen atom, and only the second ionization potential
reflects electron abstraction from the naphthalene π(au)
orbital. The second ionization potential was used to
calculate hyperbolic dependence (2), while it was not
included in the calculation of parameters of linear
relation (1) because of strong deviation.
The first group, π(au)–π naphthalene complexes
(Table 1), includes molecular complexes of 1,3,5-
trinitrobenzene with naphthalene, some alkylnaph-
thalenes, and its oxygen- and nitrogen-containing
derivatives with symmetrical arrangement of sub-
stituents. In the crystalline structure of the 1,3,5-
trinitrobenzene–naphthalene complex [24], the centers
of the donor and acceptor molecules appear spatially
close to each other. Monoalkoxy derivatives and their
nitrogen analogs were not included into the first group.
These substituents appreciably affect the π-electron
density distribution over the naphthalene ring, thus
distorting centrosymmetric orientation of the acceptor
The complex of 1,3,5-trinitrobenzene with 1,3-
dimethyl-2,3-dihydroperimidine was conceivably included
into the group of naphthalene π(au)–π complexes. The
donor molecule is characterized by a low first adiabatic
ionization potential (6.40 eV). Taking into account that
deviations from linear relation (1) are observed in the
region corresponding to low ionization potentials
[25, 26], the charge-transfer maximum for the complex
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 79 No. 11 2009

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PRYALKIN
with 1,3-dimethyl-2,3-dihydroperimidine was not used
in the calculation of linear dependence (1).
complexes) constituted the first type. Type II
complexes were those derived from neutral species and
molecular ions (ion–molecule complexes), and
complexes of type III were ion pairs, i.e., complexes
formed by oppositely charged species. Another
approach was based on the energy of formation of
complexes from components. According to this
approach, weak, medium-strength, and strong com-
plexes were distinguished [1]. Kuleshova [29]
discussed classifications of H-complexes on the basis
of the number of intermolecular interactions (H-bonds)
with participation of one molecule. It should be
emphasized that, in keeping with Mulliken’s classifica-
tion, H-associates are n–σ complexes.
The groups of 1- and 2-aminonaphthalene com-
plexes include those formed by 1,3,5-trinitrobenzene
with naphthalene derivatives having unsubstituted
amino- and hydroxy groups. These groups of
complexes are analogous to the group of aniline com-
plexes described previously [27]. They are charac-
terized by both π(au)–π interactions between the
aromatic rings in the donor and acceptor and
interactions between the nitro groups in the acceptor
and amino and/or hydroxy groups in the donor
(hydrogen bonds or n–σ interaction). The occurrence
of an additional n–σ interaction appreciably changes
parameters of correlation (1). The slope of the
dependence of the energy of the charge-transfer bands
upon ionization potential of the donor molecule is
lower than that found for the naphthalene π(au)–π
complexes, which is related to different directions of
electron transitions. n–σ Interaction implies electron
transition from the nitro compound to naphthalene
derivative, while π(au)–π interaction involves the
reverse transition.
The most widely recognized is the classification of
complexes proposed by Mulliken and Person [1] who
systematized complexes with respect to interacting
orbitals of the components (Table 2): σ- and π-bonding
and antibonding orbitals, n- and v-nonbonding orbitals.
This approach distinguishes 9 types of complexes
(Table 4). Mulliken’s classification is in fact classifica-
tion of intermolecular orbital interactions (bonds)
rather than classification of complexes. Some dis-
advantages of Mulliken’s classification were noted in
[30, 31].
Centrosymmetric coordination of the acceptor with
respect to the donor [simultaneous π(au)–π and n–σ
interactions] is allowed in naphthalene-1-amine com-
plexes, whereas such coordination is broken in going
to 2-hydroxy- or 2-aminonaphthalenes (group of
naphthalen-2-amine complexes). In this case, the ac-
ceptor should be oriented above the naphthalene ring
with substituent. It should be noted that dependences
(1) for 1- and 2-aminonaphthalene complexes are
parallel, indicating similar interactions in complexes
belonging to these groups. The hν—IP dependence for
the naphthalene-1-amine group appears below the
corresponding dependence for naphthalene-2-amine
complexes. This means that interaction between the
components in the former group is stronger than in the
latter. It is also notable that the above dependences are
parallel not only to each other but also to the
dependence found for aniline complexes (a = 0.459,
b = –0.427 [25, 26]) which covers a larger number of
compounds; the groups of 1- and 2-aminonaphthalene
complexes were isolated by analogy.
Taking into account divisions of molecular com-
plexes formed by different acceptors, in particular
1,3,5-trinitrobenzene [25–27], 1,3-dinitrobenzene [32],
and iodine [33], and criticism given in [30, 31, 34], let
us consider drawbacks of Mulliken’s classification.
(1) Only pair interactions are considered: a complex
is formed from one donor molecule and one acceptor
molecule. This concept is fixed to such extent that
even in chemical textbooks donor–acceptor complexes
are defined as complexes always consisting of two
molecules: donor and acceptor [35]. Compounds with
a more complex composition, i.e., those including
several donor molecules (similar or different) and
several acceptor molecules (similar or different) are
considered to be formed as a result of pair interactions.
It is even more difficult to determine the type of a
complex according to Mulliken if it includes more than
two different molecules, e.g., the complex hexamethyl-
benzene–nitrobenzene–aluminum trichloride [36] (see
figure, complex A). In this complex, three different
molecules are involved in different interactions, π–π
and n-σ.
Several approaches to classification of molecular
complexes have been reported [1, 3–7, 28, 29].
Kampar [28] distinguished three types of molecular
complexes, assuming electrostatic interaction as the
main contribution to stabilization of complexes (Table 3).
Complexes formed by neutral species (molecular
(2) The structure (symmetry) of interacting orbitals
is not taken into account explicitly (Table 4). The
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MOLECULAR COMPLEXES OF 1,3,5-TRINITROBENZENE
AlCl3
2363
O–
O
O–
H
O
H
N+
N+
N
CH3
H3C
H3C
CH3
O2N
NO2
CH3
CH3
B
A
NO2
H
N(CH3)2
H
N
N
N
O
O2N
NH
HN
NO2
H N
O
O
O
N
C
D
H
H
N
N
O
O
N
O
O
HN
N H
H
H
NH
N
OH
O
N
H
H
F
E
Intermolecular interactions in the complexes hexamethylbenzene–nitrobenzene–aluminum trichloride (A),1,3,5-trinitrobenzene–
aniline (B), thymine–adenine (C), procaine–1,3,5-trinitrobenzene (D), p-benzoquinone–hydroquinone (E), and cytosine–guanine (F).
necessity of consideration of the orbital symmetry was
noted previously [30]. This is exceptionally important
for π-orbitals characterized by complex steric struc-
ture. Therefore, complexes are divided primarily into
derivatives of benzene, naphthalene, and other
polycyclic hydrocarbons [25]. Division of complexes
with respect to benzene orbital structure was demon-
strated using π–σ-complexes of iodine with benzene
derivatives [33]. These complexes were divided into
two groups, depending on the type of donor orbital of
the aromatic compound: π(b1) or π(a2). On the basis of
the structure of two highest occupied molecular
orbitals of benzene, two different structures of the
benzene–iodine complex were proposed [1].
Table 4. Classification of molecular complexes according to
Mulliken [1]
Table 3. Classification of molecular complexes according to
Kampar [28]
Initial
components
Orbital in the acceptor molecule
Orbital in the
Type
Ground state
D ···· A
Excited state
D+ ···· A–
donor molecule
σ
v
π
D + A
I
σ
n
π
σ–σ
n–σ
π–σ
σ–v
n–v
π–v
σ–π
n–π
π–π
D– + A
D + A+
D– ···· A
D ···· A+
D ···· A–
D+ ···· A
IIa
IIb
D– + A+
D– ···· A+
D ···· A
III
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2364
PRYALKIN
(3) The formation of a single bond between the
quinone [24] (structure E) and NA base pair cytosine–
guanine (three hydrogen bonds; structure F).
components is assumed, i.e., intermolecular interaction
involves only one donor orbital of the donor molecule
and one vacant orbital of the acceptor molecule.
Possible interactions of other orbital couples (donor–
acceptor) are not considered by Mulliken. A complex
composed of two molecules (or other entities) is
formed via one intermolecular bond. Donor molecule
M1 affords an occupied orbital for the formation of
intermolecular bond, while acceptor molecule M2
gives a vacant orbital (the direction of electron density
transfer is indicated with an arrow).
Quadruple intermolecular bond in binary com-
plexes may be represented by three versions:
M1
M1
M1
M2
M2
M2
Quintuple and higher-order bonds could give rise to
even more versions. Several intermolecular
interactions between components of a complex are
possible only if the corresponding interacting orbitals
could freely approach each other. It is also necessary
that orbitals of one molecule be complementary to
appropriate orbitals of the other molecule, as in
nucleobase pairing (see figure; complexes C and F).
M1→M2
Two modes of double intermolecular bonding is
possible, which differ by the direction of electron
density transfer.
(4) Systematization of complexes is based only on
parameters of their precursors (components), while
parameters of the complexes are not taken into
account. The structure of complexes in the explicit
form is absent in Mulliken’s classification, though it is
necessarily discussed in all studies on molecular
complexes. For comparison, classification of organic
compounds involves explicit structural specification of
each class of compounds. It is notable that IUPAC
nomenclature [38] recommends to name addition
compounds by indicating the names of individual
components and the numbers of their molecules
without noting mutual arrangement of the components.
M2
M2 and M1
M1
As applied to the first mode of double inter-
molecular interaction, separation of the components
into donor and acceptor molecules makes no sense. It
was proposed [9] to use the terms receptor (in this
work, naphthalene derivatives) and substrate (1,3,5-
trinitrobenzene).
The first mode of double intermolecular interaction
is observed in 1,3,5-trinitrobenzene complexes with
aniline [27] (see figure, complex B). In this case, the
complex is formed via π–π interaction between the
aromatic systems of the components and interaction
between n electrons on the oxygen atom in the nitro
group and σ orbital of the amino group of aniline
(hydrogen bond). The nucleic acid base pair thymine–
adenine involves two hydrogen bonds (n–σ interaction)
with opposite directions of electron density transfer
(see figure, complex C).
It is known [39, 40] that classification of organic
compounds is based mainly on the number, nature, and
valence state (“atomicity” according to A.M. Butlerov)
of atoms constituting a molecule, as well as on the
structure of the latter. Classification of the simplest
molecular complexes (supermolecules according to
Lehn [9]) is based primarily on the number, type, and
structure of interacting orbitals, which determine the
structure of a complex (intermolecular conformation).
The number and structure of molecules (or other
entities) constituting a complex should also be taken
into account.
The complex of procaine with 1,3,5-trinitrobenzene
[37] is an example of the second mode of double
intermolecular bonding: π–π* interaction between the
aromatic systems of the components is accompanied
by an interaction (at the opposite side of the aromatic
ring of trinitrobenzene) between the n orbital of the
nitrogen atom of the donor and π* orbital of the aro-
matic ring in the acceptor (see figure, complex D).
EXPERIMENTAL
Chloroform (solvent) of analytical grade was
preliminarily dried over calcium chloride and distilled
under atmospheric pressure. 1,3,5-Trinitrobenzene
(acceptor) of analytical grade was recrystallized from
carbon tetrachloride. The concentration of complexes
in solution was 0.005 M. The following compounds
were used as donor components: acenaphthene,
naphthalen-1-ol, naphthalen-2-ol, naphthalen-1-amine,
Two modes of triple intermolecular bond are
possible.
M1
M2 M1
M2
Examples of triple interaction of the second type
are the complexes of p-benzoquinone with hydro-
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MOLECULAR COMPLEXES OF 1,3,5-TRINITROBENZENE
2365
10. Vovna, V.I. and Vilesov, F.I., Usp. Foton., 1975, no. 5,
naphthalene-2-amine, and 1,8-dimethylnaphthalene
(analytical grade all). 1- and 2-Methoxynaphthalenes
were synthesized by alkylation of the corresponding
hydroxy derivatives with dimethyl sulfate according to
the standard procedure [41] and were purified by
distillation under reduced pressure. The concentration
of donor components in solution exceeded the
concentration of 1,3,5-trinitrobenzene by a factor of 30
to 100.
p. 3.
11. Energii razryvov khimicheskikh svyazei. Potentsialy
ionizatsii i srodstvo k elektronu (Dissociation Energies
of Chemical Bonds. Ionization Potentials and Electron
Affinities), Kondrat’ev, V.N., Ed., Moscow: Nauka,
1974.
12. Levin, R.D. and Lias, S.G., Ionization Potential and
Appearance Potential Measurements. 1971–1981, U.S.
Dep. Commerce Nat. Bur. Stand. Nat. Stand. Ref. Data
Ser, 1982, no. 71.
13. Vovna, V.I., Elektronnaya struktura organicheskikh
soedinenii po dannym fotoelektronnoi spektroskopii
(Electronic Structure of Organic Compounds according
to the Data of Photoelectron Spectroscopy), Moscow:
Nauka, 1991.
14. Bier, A., Recl. Trav. Chim. Pays–Bas, 1956, vol. 75,
no. 6, p. 866.
15. Kysel, O., Z. Phys. Chem., 1974, vol. 89, nos. 1–4,
p. 62.
16. Smets, G., Zeegers, B., and Navarre, A., Bull. Inst. Polit.
IASI, 1970, vol. 16, nos. 1–2, p. 81.
The UV spectra of molecular complexes were
measured in chloroform at room temperature using
quartz cells with a cell path length of 1 cm. The
reference cell was filled with the solvent. The optical
density was determined with a step of 1 nm on an SF-
46 spectrophotometer. The spectrum of the 1,3,5-
trinitrobenzene complex with 1,8-dimethylnaphthalene
was recorded on an Specord M-40 spectrophotometer
with automatic determination of the charge-transfer
band maximum with subsequent averaging of the data
of five measurements.
Correlation analysis was performed according to
the procedures described previously [6, 8] using the
following relationship between wavelength and energy
[42]: hν = 1239.8 λ–1.
17. Heilbroner, E., Hoshi, T., von Rosenberg, J.L., and
Hafner, K., Nouv. J. Chim., 1977, vol. 1, no. 2, p. 105.
18. Adams, S.P. and Whitlock, H.W., J. Org. Chem., 1981,
vol. 46, no. 17, p. 3474.
19. Pozharskii, A.F., Suslov, A.N., Starshikov, N.M.,
Popova, L.L., Klyuev, N.A., and Adanin, V.A., Zh. Org.
Khim., 1980, vol. 16, no. 10, p. 2216.
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