A Quantum Chemical Study on Levomycetin Interaction with Silica Surface
The biological activity of D(-)-threo-isomer of levomycetin is connected with presence of hydrogen bonding between hydroxyl groups of its alicyclic form. When grafted on silica surface (via impregnation), levomycetin increases its antimicrobial capability. Adsorption-induced changes in the structure...
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| Опубліковано в: : | Хімія, фізика та технологія поверхні |
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| Дата: | 2010 |
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| Мова: | Англійська |
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Інститут хімії поверхні ім. О.О. Чуйка НАН України
2010
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| Назва журналу: | Digital Library of Periodicals of National Academy of Sciences of Ukraine |
| Цитувати: | A Quantum Chemical Study on Levomycetin Interaction with Silica Surface / A.A. Kravchenko, T.V. Krupska., E.M. Demianenko, A.G. Grebenyuk, V.S. Kuts, V.V. Lobanov // Хімія, фізика та технологія поверхні. — 2010. — Т. 1, № 3. — С. 242-247. — Бібліогр.: 8 назв. — англ. |
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Digital Library of Periodicals of National Academy of Sciences of Ukraine| _version_ | 1859684741629870080 |
|---|---|
| author | Kravchenko, A.A. Krupska, T.V. Demianenko, E.M. Grebenyuk, A.G. Kuts, V.S. Lobanov, V.V. |
| author_facet | Kravchenko, A.A. Krupska, T.V. Demianenko, E.M. Grebenyuk, A.G. Kuts, V.S. Lobanov, V.V. |
| citation_txt | A Quantum Chemical Study on Levomycetin Interaction with Silica Surface / A.A. Kravchenko, T.V. Krupska., E.M. Demianenko, A.G. Grebenyuk, V.S. Kuts, V.V. Lobanov // Хімія, фізика та технологія поверхні. — 2010. — Т. 1, № 3. — С. 242-247. — Бібліогр.: 8 назв. — англ. |
| collection | DSpace DC |
| container_title | Хімія, фізика та технологія поверхні |
| description | The biological activity of D(-)-threo-isomer of levomycetin is connected with presence of hydrogen bonding between hydroxyl groups of its alicyclic form. When grafted on silica surface (via impregnation), levomycetin increases its antimicrobial capability. Adsorption-induced changes in the structure and energy parameters of levomycetin molecules probably responsible of its activity have been studied by means of quantum chemistry. It has been found that descriptors of levomycetin bioactivity can be values of the LUMO energy and O-H…O hydrogen bond length within the propanediol fragment of the molecule.
Біологічну активність D(-)-трео-ізомера левоміцетину пов’язують з присутністю в його аліциклічній формі водневого зв’язку між гідроксильними групами. Адсорбційно закріплений (шляхом імпрегнування) левоміцетин на поверхні кремнезему підвищує антимікробну здатність. Методами квантової хімії досліджено зміни структурних та енергетичних параметрів молекул левоміцетину, обумовлені адсорбцією, які можуть відповідати за його активність. Виявлено, що дескрипторами біологічної активності левоміцетину можуть бути енергія НВМО та довжина водневого зв’язку O-H…O в пропандіольному фрагменті молекули.
Биологическую активность D(-)-трео-изомера левомицетина связывают с присутствием в его алициклической форме водородной связи между гидроксильными группами. Адсорбционно закрепленный (путем импрегнирования) левомицетин на поверхности кремнезема повышает антимикробную способность. Методами квантовой химии изучены изменения структурных и энергетических параметров молекул левомицетина, обусловленные адсорбцией, которые могут отвечать за его активность. Обнаружено, что дескрипторами биологической активности левомицетина могут быть энергия НВМО и длина водородной связи O-H…O в пропандиольном фрагменте молекулы.
|
| first_indexed | 2025-11-30T21:27:03Z |
| format | Article |
| fulltext |
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_____________________________________________________________________________________________
* Corresponding author kravchenko@zeos.net
242 ���� 2010. � . 1. � 3
UDC 547.568:544.723:544.183
A QUANTUM CHEMICAL STUDY ON LEVOMYCETIN
INTERACTION WITH SILICA SURFACE
A.A. Kravchenko*, T.V. Krupska., E.M. Demianenko, A.G. Grebenyuk,
V.S. Kuts, V.V. Lobanov
Chuiko Institute of Surface Chemistry of National Academy of Sciences of Ukraine
17 General Naumov Street, Kyiv 03164, Ukraine
The biological activity of D(-)-threo-isomer of levomycetin is connected with presence of hy-
drogen bonding between hydroxyl groups of its alicyclic form. When grafted on silica surface (via
impregnation), levomycetin increases its antimicrobial capability. Adsorption-induced changes in
the structure and energy parameters of levomycetin molecules probably responsible of its activity
have been studied by means of quantum chemistry. It has been found that descriptors of levomycetin
bioactivity can be values of the LUMO energy and O-H…O hydrogen bond length within the pro-
panediol fragment of the molecule.
INTRODUCTION
High disperse silica can act as a pronounced
detoxicant and promotes bioactivity of a row of
remedies [1], so their adsorption grafting on silica
surface open a way to create a new generation of
composite antibiotic-resistent medical products [2].
The effect was studied in [3] of a silica-
levomycetin composite on development of
E. coli cells and it was shown that in the solution
containing levomycetin grafted on silica surface
the E. coli cells number was 3.75 times lesser
than that in the solution of pure antibiotic of the
same concentration.
Levomycetin is an antibiotic of a wide
spectrum of action concerning both gram-
positive and gram-negative microorganisms. Its
molecule (LV) (Fig. 1) contains n-nitrophenyl
radical (I), propanediol group (II), and di-
chloroacetamide group (III).
Fig. 1. Structural formula of the bioactive form of
levomycetin (� – n-nitrophenyl radical, �� – pro-
panediol group, ��� – dichloroacetamide group)
n-Nitrophenyl radical (Fig. 1, I) has a con-
siderable effect on the antibiotic activity both due
to its electronic nature and strong polarization of
the propanediol group, geometric size of this part
of the molecule having no key significance. When
the nitrogroup of LV molecule is substituted for by
less electronegative radicals (CN, Cl, H, �� 3 and
so on), an essential decrease in bioactivity of such
forms or even its loss takes place [4].
The propanediol part of LV molecule (its has
a D(-)-threo-configuration at C1 and C2 carbon
atoms) play an essential role in the specific inter-
action between LV and target (Fig. 1, �� ). This
configuration secures a close stationing of hy-
droxyl groups with hydrogen bonds between them
what, according to [5–7], conditions formation of a
bioactive closed alicyclic configuration of LV
molecule. Such a configuration is not realized for
other stereoisomers [4]. The loss of di-
chloroacetamide fragment of the molecule results
in the complete loss in its bioactivity [7].
Thus, the propanediol and dichloroacetamide
fragments of LV molecule form active sites pro-
viding addition of this molecule to specific sites
of some bacterial proteins so exclusing the latter
from the normal exchange of microbial cells. Ac-
cording to [4–7], the antibiotic action of LV is
controlled by three factors: (1) strong acceptor
capability of n-nitrophenyl radical; (2) strongly
defined geometry size and relative conformation
of the propanediol chain; (3) strong polarizing
effect of the dichloroacetamide group which
A Quantum Chemical Study on Levomycetin Interaction with Silica Surface
_____________________________________________________________________________________________
���� 2010. � . 1. � 3 243
should simultaneously satisfy definite geometry
conditions. The superposition of these effects
causes a strong interaction between antibiotic
molecule and specific peptide groups of some
ensimes what results in the dysbolism in micro-
organisms.
Unfortunately, there are few articles in the
literature concerning studies on the effect of the
spatial and electronic structures of levomycetin
molecules as well as of their energy characteris-
tics on their antimicrobial activity. As the eluci-
dation of interrelations between structural char-
acteristics, bioactivity, and electron density re-
distribution due to changes in the electronegativ-
ity of substituent of the functional groups of free
and adsorbed LV molecules is rather compli-
cated experimentally, quantum chemical studies
on these systems are rather relevant.
OBJECTS AND METHODS
The object under study was levomycetin. It
is an antibiotic of a wide action spectrum con-
cerning both gram-positive and gram-negative
microorganisms. Levomycetin has four spatial
isomers but only D(-)-threo-isomer in closed
alicyclic form has an antibacterial activity. The
rest L(-)-threo-, D(-)-erythro-, and L(-)-erythro-
isomers have activities of 0.4, 0.4, and 1 to 2%
respectively of that of D(-)-threo-isomer [5–7].
According to the level of effect on the anti-
microbial activity, functional derivatives with
substituted nitrogroup can be arranged into a
row where their positions are qualitatively rele-
vant to decrease in their electronegativities [4]
NO2>CN>CO2Me>Cl(Br)>SO2Me>SO2NH2>H>Me.
Thus, the bioactivities of D(-)-threo-R-isomers
(R – functional groups –CN, –Cl, and –� ) are
of 95, 20, and 0% respectively of that of D(-)-
threo-nitro-isomer.
In order to clarify the effect of adsorption
on the antibiotic properties, quantum chemical
calculations have been carried out on spatial and
electronic structure as well as on thermodynamic
characteristics of levomycetin C11H12Cl2N2O5
molecules and its adsorption complexes at the
silica–water interface. All the calculations have
been carried out by means of PC GAMESS pro-
gram package (version 7.1 F) within ab initio
Hatree-Fock method and density functional the-
ory method (B3LYP) with basis set 3-21G**.
Separated results were checked with basis set
6-31G**. The models for silica surface were
polysilicate acids clusters containing 4, 8, and 13
silicon-oxygen tetrahedra. Taking into account
the result obtained experimentally that the LV
amount adsorbed on silica surface from alcohol
is more than that adsorbed from aqueous me-
dium [3], we also have carried out calculations
on the adsorption energy of the complexes of LV
molecule–solvent–silica (5 alcohol molecules
and/or 15 water molecules) stationed between
LV molecule and silica surface. The direct con-
tact has been also examined between levomy-
cetin molecule and silica surface.
RESULTS AND DISCUSSION
Quantum chemical calculations have been
carried out on equilibrium spatial structure of four
LV isomers (D(-)-threo, L(-)-threo, D(-)-erythro,
D(-)-erythro). The alicyclic form of D(-)-threo-
isomer (Fig. 2) appears to be the most stable one
where a hydrogen bond is formed between hy-
droxyl groups of aminopropanediol group (Fig. 1,
�� ). The hydrogen bond length d(�� …� ) be-
tween hydroxyl groups is of 1.694 Å as compared
by density functional theory method (B3LYP, 3-
21G**). When nitrogroup in D(-)-threo-isomer is
substituted for groups –CN, –Cl, –H, or –�� 3,
this value increases and equals to 1.696, 1.700,
1.706, and 1.707 Å, respectively (see Table) what
testifies an effect of the substituent electronega-
tivity on the electronic structure of the models of
levomycetin derivatives. The same dependence in
d(�� …� ) calculations has been found in case of
use of DFT method (B3LYP, 6-31G**) with the
correlation coefficient between d(3-21G**) and
d(6-31G**) values of 0.998. Analogous correla-
tions have been obtained due to comparison of
the energies of the frontier orbitals (HOMO and
LUMO) found with these basis sets. This fact
gives us a reason, in order to reduce the comput-
ing time, to use the lesser basis set for studies of
the models including large silica clusters.
Characterizing frontier molecular orbitals
(HOMO, LUMO) gives us an opportunity to
forecast the probable reaction route involving
levomycetin and to determine the sites of elec-
trophilic and nucleophilic attacks. Thus, an
electrophil should attack the LV atoms with
orbitals paying the maximum income into the
HOMO whereas the site of the most probable
nucleophil attack should be the LV atoms with
orbitals paying the maximum income into the
A.A. Kravchenko, T.V. Krupska., E.M. Demianenko et al.
_____________________________________________________________________________________________
244 ���� 2010. � . 1. � 3
LUMO. A graphic image is presented in Fig. 3
of the frontier orbitals of the D(-)-threo-NO2-
isomer of LV molecule in the alicyclic form
along with those of relative D(-)-threo-R-
isomers (R= –� N, –Cl, –H, –CH3).
Fig. 2. Equilibrium spatial structure of the alicyclic
form of D(-)-threo-isomer of LV molecule as
calculated by density functional theory method
(B3LYP/3-21G**)
The results of calculations testify that the
HOMO is practically equally localized at the at-
oms of aromatic nucleus (Fig. 1, �) as independ-
ent on the nature of the substituent functional
groups what can point out the absence of the ef-
fect of definite group on the specific interaction
with a biological target. Nevertheless it should be
taken into consideration that for levomycetins
with the great biological activity (R = NO2 or � N,
see Table) the HOMO is localized also at the
oxygen and nitrogen atoms of dichloroacetamide
group (Fig. 1, ��� ). At the same time, the oxygen
atom of carbonyl group of D-(-)threo-NO2-LV
has the largest value of LCAO coefficient in the
HOMO (Fig. 3). This fact can testify that the bio-
logical activity of levomycetin is conditioned by
specific bonding of these atoms with electrophilic
areas of biological objects.
It is seen also from Fig. 3 that in biologically
active molecules of D(-)-threo-NO2-isomer and its
analogue with � N-group, the LUMO is localized
at n-NO2- and n-� N-aromatic fragments whereas
in the rest (biologically inert) molecules with –Cl,
–H, and –CH3 groups, the LUMO is localized at
dichloroacetamide fragment. So, levomycetin
molecule can realize bonding with nucleophilic
areas of biological systems via aromatic system.
The greater LUMO energy, the lesser both electron
acceptor capability of levomycetin analogues and
their biological activities (see Table). At the same
time, the lesser LUMO energy, the greater LCAO
coefficients at the aromatic system of relative
levomycetin. So, the LUMO energy can be an
electron descriptor of levomycetin molecular struc-
ture and biological activity [8].
Fig. 3. Graphic image of the HOMO and LUMO of
the molecules of D(-)-threo-R-isomers of
levomycetin (R = – NO2, –� N,–Cl, –H, –CH3
B3LYP/6-31G**)
An analysis of the values of hydrogen
bond lengths in the propanediol fragment of
LV molecule (Fig. 1, II ) with substituted func-
tional group (see Table) performs a clear cor-
relation with the biological activity
biological activity = -8203*(d) +13992,
r=0.945, n=5. (*)
It is remarkable that even little increase in hy-
drogen bond length results in the practical loss
of the biological activity of LV.
The results of calculations on the interaction of
isolated hydroxyl group of the tetrahedral cluster
containing 4 silicon-oxygen tetrahedra, with groups
–NO2, –C=O, –NH, –O� of the alicyclic form
of D(-)-threo-isomer of levomycetin molecule
have shown that the lowest energy relates to the
A Quantum Chemical Study on Levomycetin Interaction with Silica Surface
_____________________________________________________________________________________________
���� 2010. � . 1. � 3 245
Table. Calculated data for isolated and adsorbed levomycetin molecule on silica surface
HOMO energies, eV
LUMO enrgies, eV
d – hydrogen bond
length between
–�� groups, Å Complex
6-31G** 3-21G** 6-31G** 3-21G** 6-31G** 3-21G**
Bioactivity of
compounds,
%, (E.coli
being an
example) [6]
Isolated LV molecule
LV D(-)-threo (NO2)
(alicyclic form)
-7.246 -7.012 -2.324 -2.54 1.815 1.694 100
LV D(-)-threo (CN) -6.980 -6.838 -1.385 -1.197 1.818 1.696 95
LV D(-)-threo (Cl) -6.525 -6.482 -0.999 -1.039 1.830 1.700 20
LV D(-)-threo (H) -6.523 -6.425 -0.884 -0.920 1.835 1.706 0
LV D(-)-threo (CH3) -6.275 -6.212 -0.857 -0.893 1.838 1.707 0
Adsorption complexes
LV D(-)-threo-(NO2)
+ silica (Fig. 4b)
-7.532 -3.494 1.673
375 [7]
270 (calculated)
LV D(-)-threo-(NO2)
+ silica (Fig. 4� )
-6.768 -3.453 1.700
~20
(calculated)
structure including two hydrogen bonds between
the oxygen atom of hydroxyl group and the hy-
drogen atom of the NH group of levomycetine
molecule along with that between the hydrogen
atom of hydroxyl group and the oxygen atom of
levomycetin carbonyl group.
The adsorption complex built of the ali-
cyclic form of D(-)-threo-isomer of LV mole-
cule and of the model of silica surface contain-
ing 8 silicon-oxygen tetrahedra is for
57 kJ/mol more favorable than the adsorption
complex involving the non-cyclic form
whereas the energy of free LV molecule in
alicyclic form differs from that of non-cyclic
one only for 22 kJ/mol. The calculation of the
� G value as dependent on the temperature
within 1 to 450 K shows that the temperature
when the alicyclic form of D(-)-threo-isomer
of levomycetin molecule becomes more favor-
able than non-cyclic one at about 129 K
whereas the interaction with a silica nanopar-
ticle shifts this value to about 136 K. This can
testify an effect of silica surface on the favor-
able form of D(-)-threo-isomer and justifies
the adsorption of LV on silica surface pre-
dominantly in the biologically active form.
Adsorption complexes of LV molecule in-
teracting with a molecular model of silica sur-
face containing 13 silicon-oxygen tetrahedra
are shown in Fig. 4. It is seen that a bonding
can be realized due to forming hydrogen bonds
� –� …� and � –� …N between hydrogen at-
oms of silanol groups of silica with oxygen
atoms of nitro- and/or carbonyl groups as well
as with nitrogen atom of –NH group of LV
molecule (Fig. 4� ). In such an adsorption
complex, hydrogen bond length (d) is of
1.700 Å what corresponds to the bioactivity of
about 20% as calculated according to the
equation (*). Nevertheless, more probable (for
38 kJ/mol than previous one) is an adsorption
complex where a � –� …� hydrogen bond is
formed between silanol groups and oxygen
atoms of –NO2 and –O� groups of LV mole-
cule (Fig. 4b). The hydrogen bond length be-
tween -O� groups in the complex is somewhat
lesser (1.673 Å) than that in free levomycetin
molecule (1.694 Å). The calculated value of
biological activity is close to that found ex-
perimentally (375%) and is of 270%.
Fig. 4 shows the isolines of the LCAO co-
efficients of frontier orbitals of respective ad-
sorption complexes. The distribution of the
HOMO and LUMO over levomycetin molecule
on silica surface is seen to be similar to that of
free LV molecule (Fig. 3) with marked biologi-
cal activity. At the same time, the LCAO value
of the oxygen atom of carboxyl group for the
HOMO is greater for the b complex as com-
pared with that of the a one what can testify the
greater biological activity of LV molecule ad-
sorbed on silica surface.
A.A. Kravchenko, T.V. Krupska., E.M. Demianenko et al.
_____________________________________________________________________________________________
246 ���� 2010. � . 1. � 3
HOMO LUMO
�
HOMO LUMO
�
Fig. 4. Equilibrium spatial structures of probable ad-
sorption complexes of levomycetin on silica
surface realized due to forming hydrogen bonds
� –� …� and � –� …N between hydrogen at-
oms of silanol groups with oxygen atoms of ni-
tro- and/or carbonyl groups as well as with ni-
trogen atom of –NH group of LV molecule (� ),
and oxygen atoms of –NO2 and –O� groups of
LV molecule (b), and the LCAO coefficients
distribution over their frontier orbitals
The LUMO for both complexes is stationed
at the nitrophenyl fragment. The analysis of the
frontier orbitals testifies the greater biological
activity of the b complex as compared with that
of a one.
The position of levomycetin molecule on sili-
ca surface (simulated by eight silicon-oxygen
tetrahedra) surrounded by fifteen water mole-
cules is less favorable energetically if it directly
contacts with silanol groups than that where wa-
ter molecules are stationed between levomycetin
molecule and silica surface (the Gibbs adsorp-
tion energy is of 296 kJ/mol). Unlike that from
water, the adsorption from alcohol should be
favorable energetically (the Gibbs adsorption
energy is of -39.5 kJ/mol). This result is proved
by experimental data [3].
A correlation is seen from the Table between
the biological activity of LV and the energies of
the frontier orbitals of both free and adsorbed LV
on silica surface. A correlation also takes place
between the biological activity of LV and the hy-
drogen bond length between –�� groups.
CONCLUSIONS
It has been found that the descriptors of bio-
logical activity of LV molecules can be the hy-
drogen bond length and the energy and electron
density distribution of the frontier molecular
orbitals.
When alicyclic form of levomycetin mole-
cule is adsorbed on silica surface, a strengthen-
ing takes place of intramolecular hydrogen
bond in the propanediol fragment of levomy-
cetin molecule what causes an increase in its
bioactivity.
The interaction between levomycetin mole-
cule and silica surface is realized via proton do-
nor groups –OH and nitrogroup what is character-
ized by somewhat higher value of the formation
energy as compared with that in case of interac-
tion via groups >NH, >C=O, and –NO2.
The adsorption of levomycetin from alcohol is
more favorable thermodynamically than that from
aqueous solution what agrees with experimental
data.
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Received 15.07.2010, accepted 17.08.2010
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| id | nasplib_isofts_kiev_ua-123456789-28985 |
| institution | Digital Library of Periodicals of National Academy of Sciences of Ukraine |
| issn | 2079-1704 |
| language | English |
| last_indexed | 2025-11-30T21:27:03Z |
| publishDate | 2010 |
| publisher | Інститут хімії поверхні ім. О.О. Чуйка НАН України |
| record_format | dspace |
| spelling | Kravchenko, A.A. Krupska, T.V. Demianenko, E.M. Grebenyuk, A.G. Kuts, V.S. Lobanov, V.V. 2011-11-27T16:10:49Z 2011-11-27T16:10:49Z 2010 A Quantum Chemical Study on Levomycetin Interaction with Silica Surface / A.A. Kravchenko, T.V. Krupska., E.M. Demianenko, A.G. Grebenyuk, V.S. Kuts, V.V. Lobanov // Хімія, фізика та технологія поверхні. — 2010. — Т. 1, № 3. — С. 242-247. — Бібліогр.: 8 назв. — англ. 2079-1704 https://nasplib.isofts.kiev.ua/handle/123456789/28985 547.568:544.723:544.183 The biological activity of D(-)-threo-isomer of levomycetin is connected with presence of hydrogen bonding between hydroxyl groups of its alicyclic form. When grafted on silica surface (via impregnation), levomycetin increases its antimicrobial capability. Adsorption-induced changes in the structure and energy parameters of levomycetin molecules probably responsible of its activity have been studied by means of quantum chemistry. It has been found that descriptors of levomycetin bioactivity can be values of the LUMO energy and O-H…O hydrogen bond length within the propanediol fragment of the molecule. Біологічну активність D(-)-трео-ізомера левоміцетину пов’язують з присутністю в його аліциклічній формі водневого зв’язку між гідроксильними групами. Адсорбційно закріплений (шляхом імпрегнування) левоміцетин на поверхні кремнезему підвищує антимікробну здатність. Методами квантової хімії досліджено зміни структурних та енергетичних параметрів молекул левоміцетину, обумовлені адсорбцією, які можуть відповідати за його активність. Виявлено, що дескрипторами біологічної активності левоміцетину можуть бути енергія НВМО та довжина водневого зв’язку O-H…O в пропандіольному фрагменті молекули. Биологическую активность D(-)-трео-изомера левомицетина связывают с присутствием в его алициклической форме водородной связи между гидроксильными группами. Адсорбционно закрепленный (путем импрегнирования) левомицетин на поверхности кремнезема повышает антимикробную способность. Методами квантовой химии изучены изменения структурных и энергетических параметров молекул левомицетина, обусловленные адсорбцией, которые могут отвечать за его активность. Обнаружено, что дескрипторами биологической активности левомицетина могут быть энергия НВМО и длина водородной связи O-H…O в пропандиольном фрагменте молекулы. en Інститут хімії поверхні ім. О.О. Чуйка НАН України Хімія, фізика та технологія поверхні Теорія хімічної будови, реакційної здатності та хімічного модифікування поверхні твердих тіл A Quantum Chemical Study on Levomycetin Interaction with Silica Surface Квантовохімічне дослідження взаємодії левоміцетину з поверхнею кремнезему Квантовохимическое исследование взаимодействия левомицетина с поверхностью кремнезема Article published earlier |
| spellingShingle | A Quantum Chemical Study on Levomycetin Interaction with Silica Surface Kravchenko, A.A. Krupska, T.V. Demianenko, E.M. Grebenyuk, A.G. Kuts, V.S. Lobanov, V.V. Теорія хімічної будови, реакційної здатності та хімічного модифікування поверхні твердих тіл |
| title | A Quantum Chemical Study on Levomycetin Interaction with Silica Surface |
| title_alt | Квантовохімічне дослідження взаємодії левоміцетину з поверхнею кремнезему Квантовохимическое исследование взаимодействия левомицетина с поверхностью кремнезема |
| title_full | A Quantum Chemical Study on Levomycetin Interaction with Silica Surface |
| title_fullStr | A Quantum Chemical Study on Levomycetin Interaction with Silica Surface |
| title_full_unstemmed | A Quantum Chemical Study on Levomycetin Interaction with Silica Surface |
| title_short | A Quantum Chemical Study on Levomycetin Interaction with Silica Surface |
| title_sort | quantum chemical study on levomycetin interaction with silica surface |
| topic | Теорія хімічної будови, реакційної здатності та хімічного модифікування поверхні твердих тіл |
| topic_facet | Теорія хімічної будови, реакційної здатності та хімічного модифікування поверхні твердих тіл |
| url | https://nasplib.isofts.kiev.ua/handle/123456789/28985 |
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