Volume 03 Issue 07-2023
12
International Journal of Advance Scientific Research
(ISSN
–
2750-1396)
VOLUME
03
ISSUE
07
Pages:
12-16
SJIF
I
MPACT
FACTOR
(2021:
5.478
)
(2022:
5.636
)
(2023:
6.741
)
OCLC
–
1368736135
A
BSTRACT
In the article, the advantages of quantum-chemical calculations in the study of the relationship between
the structure and properties of matter were presented. In order to energetically justify the structure of the
product formed as a result of the reaction of ferrocenecarbonic acid with p-aminobenzoic acid, the
structure of the optimized structures was studied in the Gaussian 98 program. Their Hartree energies were
determined and analytical data were reported.
K
EYWORDS
Gaussian program, quantum chemistry, ferrocene, ferrocenecarbonic acid, p-aminobenzoic acid,
heteroannular, Harty energies.
I
NTRODUCTION
Today, the field of science named "Computer
chemistry" is not limited to quantum-chemical
calculations, but includes a range of theoretical
methods, including various non-empirical and
semi-empirical methods of calculating the
physicochemical properties of matter, the use of
Journal
Website:
http://sciencebring.co
m/index.php/ijasr
Copyright:
Original
content from this work
may be used under the
terms of the creative
commons
attributes
4.0 licence.
Research Article
RESEARCH OF MOLECULAR-ENERGETIC PARAMETERS OF
THE SYNTHESIS OF FERROCENE CARBONIC ACID
DERIVATIVES BY QUANTUM-CHEMICAL CALCULATIONS
Submission Date:
July 01, 2023,
Accepted Date:
July 05, 2023,
Published Date:
July 11, 2023
Crossref doi:
https://doi.org/10.37547/ijasr-03-07-03
I.R. Asqarov
Andijan State University, Andijan, Uzbekistan
N.Q. To‘Lakov
Andijan State University, Andijan, Uzbekistan
Z.X. Abduraimov
Andijan State University, Andijan, Uzbekistan
Volume 03 Issue 07-2023
13
International Journal of Advance Scientific Research
(ISSN
–
2750-1396)
VOLUME
03
ISSUE
07
Pages:
12-16
SJIF
I
MPACT
FACTOR
(2021:
5.478
)
(2022:
5.636
)
(2023:
6.741
)
OCLC
–
1368736135
artificial intelligence and neural network
methods, the database covered the statistical
characteristics and dynamics of chemical
processes. This is very important for chemists to
develop skills for predicting substance properties
and reactivity, developing ways to synthesize
chemical compounds with certain properties
based on studying the relationships between
substance structure and properties [1].
The main part
The Gaussian software package is one of the most
widely used tools for performing quantum
chemical calculations. The main reason for this is
that it incorporates many quantum-chemical
methods, has high efficiency, and is easy to use. It
was first studied by Russian scientists in 1954
that the primary aromatic derivatives of
ferrocene can be obtained by diazotization
reaction, and as a result, monoaryl compounds
are mainly formed in ferrocene arylation
reactions [2, 3]. Rosenblum and his students
studied the reaction of ferrocene with aromatic
amines in the presence of various solvents. These
scientists say that ferrocene forms aromatic
complexes with aryldiazonium salts. The
resulting intermediate complexes are easily
decomposed, release free nitrogen and aryl
ferrocene is formed as a reaction product [4]. As
mentioned above, ferrocene carbonic acid and a
number of its aromatic and aliphatic derivatives
have been synthesized, and their water-soluble
mono- and dialyzamine salts have been obtained
in the literature.
Based on the above considerations and
continuing
research
on
obtaining
new
compounds of ferrocene carbonic acid, the
reaction of diazotization of ferrocene carbonic
acid with p-aminobenzoic acid was carried out in
diethyl ether medium, with the presence of
sodium nitrite and hydrochloric acid. As a result,
a hetero-annular substituted compound of
ferrocene carbonic acid was formed. Using the
method of quantum-chemical calculation, the
structures of all possible isomers of the reaction
product between ferrocene carbonic acid and p-
aminobenzoic acid were constructed.
Schemes of the structures of these isomers are
given below:
Volume 03 Issue 07-2023
14
International Journal of Advance Scientific Research
(ISSN
–
2750-1396)
VOLUME
03
ISSUE
07
Pages:
12-16
SJIF
I
MPACT
FACTOR
(2021:
5.478
)
(2022:
5.636
)
(2023:
6.741
)
OCLC
–
1368736135
C
O
O
H
C
O
O
H
COOH
C
O
O
H
HOOC
C
O
O
H
Fe
COOH
H
2
N
Fe
COOH
Fe
Fe
+
C
O
O
H
HOOC
Fe
C
O
O
H
HOOC
Fe
C
O
O
H
HOOC
Fe
C
O
O
H
HOOC
Fe
(1)
(2)
(3)
(4)
(5)
(6)
(7)
Figure 1. Determining which isomer corresponds to the structure of the product.
To determine which isomer the structure of the product corresponds to, the optimized structures of
possible isomers 1, 2, 3, 4, 5, 6, and 7 were calculated by Hartree energies (EHart.) DFT/B3LYP hybrid
method 3-21G of the software package "Gaussian 98". and the differences between them (DE) were
determined. The calculation results are presented in the table below.
Table 1. Hartree energies of the optimized structures of the isomers of the reaction product
between ferrocene carbonic acid and p-aminobenzoic acid and their differences.
isomers
ЕHart., кJ/mol
ΔЕ, (J)
Dipol moments
1
-2247,1399
0
2,7363
2
-2247,1366
0,33
4,1586
Volume 03 Issue 07-2023
15
International Journal of Advance Scientific Research
(ISSN
–
2750-1396)
VOLUME
03
ISSUE
07
Pages:
12-16
SJIF
I
MPACT
FACTOR
(2021:
5.478
)
(2022:
5.636
)
(2023:
6.741
)
OCLC
–
1368736135
3
-2247,1372
0,27
4,3509
4
-2247,1350
0,49
4,0036
5
-2247,1360
0,39
3,1630
6
-2247,1367
0,32
5,4649
7
-2247,1377
0,22
5,3361
R
ESULT
The calculation results showed that the energy of the 1st isomer among the 1st, 2nd, 3rd, 4th, 5th, 6th and
7th isomers of the product is significantly lower than the others. So, an isomer of substance 1 is
energetically thermodynamically stable compared to others. Based on this, it can be concluded that the
main product of the reaction of ferrocene carbonic acid with p-aminobenzoic acid corresponds to structure
1. Figure 2 shows the optimized molecular structure of the reaction product using Gaussian 98 software.
Figure 2. Calculation optimized molecular structure of the product
So, based on the results of quantum-chemical calculations, the reaction between ferrocene carbonic acid
and p-aminobenzoic acid took place based on the following scheme:
Volume 03 Issue 07-2023
16
International Journal of Advance Scientific Research
(ISSN
–
2750-1396)
VOLUME
03
ISSUE
07
Pages:
12-16
SJIF
I
MPACT
FACTOR
(2021:
5.478
)
(2022:
5.636
)
(2023:
6.741
)
OCLC
–
1368736135
C
O
O
H
C
O
O
H
C
O
O H
C
O
O H
H
COOH
C
O
O H
COOH
Fe
Fe
COOH
COOH
H
2
N
Cl
-
N
2
2H
2
O
HNO
2
HCl
Fe
Fe
Cl
-
N
2
COOH
N
N
2H
2
O
Cl
-
Fe
2H
2
O
HCl
N
2
2H
2
O
+
+
+
-5
o
C
+
34
o
C
+
+
34
o
C
+
+
34
o
C
+
+
+
+
Figure 3. Scheme of the reaction between ferrocene carboxylic acid and p-aminobenzoic acid.
C
ONCLUSION
In conclusion, it can be said that quantum-
chemical calculations are important for
calculating the structure and properties of
molecular systems. Quantitative determination of
the correlation between the structure and
properties of chemical compounds allows not
only to choose the most optimal compound from
the existing substances for the manifestation of
the given properties but also provides a way to
carry out the targeted synthesis of a new
substance that manifests the given property.
determines.
R
EFERENCES
1.
N. Q. Muxamadiyev. (2016). Kimyoviy
birikmalar
tuzilishi
va
xossalarini
matematik modellash, Toshkent: Cho‘lpon
nashriyoti, 264 bet.
2.
Несмеянов, А. Н., Перевалова, Э. Г.,
Симукова, Н. А., Шейнкер, Ю. Н., &
Решетова, М. Д. (1960). Образование 1,
2, 3-
оксадиазинового цикла при
взаимодействии
1,
1'
-
диацетилферроцена
с
арилдиазониями.
In
Доклады
Академии наук (Vol. 133, No. 4, pp. 851
-
854). Российская академия наук.
3.
Little, W. F., Lynn, K. N., & Williams, R.
(1963).
A
Novel
Side
Reaction
Accompanying the Arylation of Ferrocene.
An Example of Free Radical Substitution.
Journal of the American Chemical Society,
85(19), 3055-3056.
4.
Rosemblum M., Hovebls W.G., Raneriee C.,
The structure and chemistry of Ferrocene,
IV. Mehanism p.64.
