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Ultrasound Assisted Synthesis, Molecular Structure,UV-Visible Assignments, MEP and Mulliken Charges Study of (E)-3-(4-chlorophenyl)-1-(4-methoxyphenyl) prop-2-en-1-one: Experimental and DFT Correlational

Rohit S. Shinde

Department of Chemistry, Mahatma Gandhi Vidyamandir’s Arts, Science and Commerce College,(Affiliated to Savitribai Phule Pune University, Pune (MH), India) Manmad, Taluka-Nandgaon, District- Nashik, India-423104. 

Corresponding Author E-mail: chemistry.rss@gmail.com

DOI : http://dx.doi.org/10.13005/msri/180110

Article Publishing History
Article Received on : 23-Mar-2020
Article Accepted on : 13-Apr-2021
Article Published : 13 Apr 2021
Plagiarism Check: Yes
Reviewed by: Dr. Piyush J. Patel 
Second Review by: Dr. Nutan Sadgir 
Final Approval by: Dr. Subhasis Roy
Article Metrics
ABSTRACT:

Present investigation deals with the synthesis and density functional theory study (DFT) of a chalcone derivative; (E)-3-(4-chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one (CPMPP). The synthesis of a CPMPP has been carried out by the reaction of 4-methoxyacetophenone and 4-chlorobenzalehyde in ethanol at 30 ℃ under ultrasound irradiation. The structure of a synthesized chalcone is affirmed on the basis of FT-IT, 1H NMR and 13C NMR. The geometry of a CPMPP is optimized by using the density functional theory method at the B3LYP/6-31G(d,p) basis set. The optimized geometrical parameters like bond length and bond angles have been computed. The absorption energies, oscillator strength, and electronic transitions have been derived at the TD-DFT method at the B3LYP/6-31G(d,p) level of theory for B3LYP/6-31G(d p) optimized geometries. The effect of polarity on the absorption energies is discussed by computing UV-visible results in dichloromethane (DCM). Since theoretically obtained wavenumbers are typically higher than experimental wavenumbers, computed wavenumbers were scaled with a scaling factor, and vibrational assignments were made by comparing experimental wavenumbers to scaled theoretical wavenumbers. Quantum chemical parameters have been determined and examined. Molecular electrostatic potential (MEP) surface plot analysis has been carried out at the same level of theory. Mulliken atomic charge study is also discussed in the present study.

KEYWORDS: , B3LYP/6-311G (d,p); Chalcone; DFT; HOMO-LUMO

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Shinde R. S. Ultrasound AssistedSynthesis, Molecular Structure,UV-Visible Assignments, MEP and Mulliken Charges Study of (E)-3-(4-chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one: Experimental and DFT Correlational. Mat. Sci. Res. India;18(1).


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Shinde R. S. Ultrasound AssistedSynthesis, Molecular Structure,UV-Visible Assignments, MEP and Mulliken Charges Study of (E)-3-(4-chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one: Experimental and DFT Correlational. Mat. Sci. Res. India;18(1). Available from: https://bit.ly/32adyiP


Introduction

Chalcone is the trivial name given to the α,β-unsaturated ketones,which are synthesized by condensing an aromatic aldehyde with an substituted acetophenone in the presence of a base. Chalcones are not only important precursors in the synthesis of many biologically active molecules, but they also make up a significant part of natural products1-5. Chalcones as well as their synthetic analogues show  large number of medicinal properties [6-10]. They are crucial in the production of a wide variety of remedial compounds. They have shown remarkable curative efficacy in the treatment of a variety of diseases. Chalcone-based derivatives have gotten a lot of attention because of their simple structures and diverse pharmacological effects 6-10. The synthesis of these compounds has been reported using a variety of techniques and schemes.Aldol condensation and Claisen- Schmidt reaction continue to be the most widely used processes for synthesis of chalcones. In the presence of an aqueous alcoholic alkali, Claisen-Schmidt condensation occurs between equimolar amounts of a substituted acetophenone and substituted aldehydes. Chalcones and their heterocyclic analogues have a wide range of pharmacological properties, including anticancer, antioxidant, anti-inflammatory, antifungal, antiviral, antibacterial, antiproliferative, antitumor, antimalarial, antidiabetic, anticonvulsant, and many others, making them a significant scaffold in medicinal chemistry 16-26. Green Chemistry has played vital role for designing many synthetic molecules without causing environmental hazards 27-37. In that ultrasound technique is proved to be highly efficient. DFT is a method that can provide a good deal of information regarding the physical and chemical behavior of the molecules 38-53. In this unique circumstance, I would like to present current research on ultrasound assisted synthesis, molecular structure, UV-visible assignments, MEP, and Mulliken charges study of (E)-3-(4-chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one: a DFT and experimental study correlational.

Experimental

Chalcones were synthesized by base catalyzed Claisen‐Schmidt condensation reaction of appropriately 4-methoxyacetophenone1 and 4-chlorobenzalehydeby literature method. Anequimolar mixture of 4-methoxyacetophenone and 4-chlorobenzalehyde in 10 mL ethanol in a 50 mL conical flask equipped. Then appropriate amount of KOH solution was added drop wise to the reaction mixture. The alkaline mixture was exposed to ultrasound irradiation until formation of the product (checked by TLC). After this, reaction mixture was neutralized by 1:1 HCl whereby the precipitation occurred. On filtering off, the crude chalconewas dried in air and recrystallized by ethanol to give pale yellow crystals of chalcone 3.

 Scheme 1: Synthesis of titled compound

Vol18No1_Ult_Roh_sch1
Click on image to enlarge

Table 1: Physicochemical and Spectral data of CPMPP molecule

Systematic Name of the Product

(E)-3-(4-Chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one

Abbreviation used

CPMPP

Physicochemical data

Yield: 88%, Colour: pale yellow crystals,

FT-IR

IR (KBr, cm-1)

470, 532.35, 694.37, 771.53, 833, 995, 1087, 1211, 1327, 1489, 1597, 1666, 3047

1H NMR

(400 MHz, CDCl3)

3.90 (s, 3H), 6.97­−7.01(m, 2H), 7.37­−7.41 (m, 2H), 7.52 (d, J = 15.7 Hz, 1H), 7.55−7.59 (m, 2H), 7.75 (d, J = 15.7 Hz, 1H), 8.02−8.06 (m, 2H)

13C NMR

(100 MHz, CDCl3)

55.65, 114.05, 122.44, 129.33, 129.66, 130.98, 131.07, 133.74, 136.30, 142.55, 163.70, 188.48.

 Computational study

DFT calculations were performed on an Intel (R) Core (TM) i5 computer using Gaussian-03 program package without any constraint on the geometry. The geometry of the molecules studied in this is optimized by DFT/B3LYP method using 6-31G(d,p) basis set [54]. The FMO analysis and quantum chemical study has been performed using same basis set. Absorption energies (λ in nm), Oscillator strength (ƒ), and Transitions of title molecule have been calculated at TD-B3LYP/6-31G(d,p) level of theory for B3LYP/6-31G(d,p) optimized geometries. To investigate the reactive sites of the title molecules, the molecular electrostatic potential (MEP) was computed using the same method. All the calculations were carried out for the optimized structure in the gas phase. 

Results and Discussion

Optimized Molecular Structure

The optimized molecular structure of the title molecule CPMPP is given in Figure 1. The molecule CPMPP is having C1 point group symmetry and the dipole moment is 3.1533 Debye. The optimized geometrical parameters; bond lengths and bond angles of the title molecule have been computed and presented here in Table 2 and Table 3. In the molecule CPMPP, the C=O (C11-O16) bond length is 1.2314Å. The C-Cl (C24-Cl28) bond length is 1.7559 Å. The bond lengths in C-O are 1.359Å (C1-O27) and 1.422Å (O27-C29). Amongst aromatic C=C bond lengths, C17-C19 bond is the longest (1.4086Å) and the shortest is C2-C3 (1.3865Å). Other bond lengths are also in good agreement. All the bond angles are also in good agreement.

Figure 1: Optimized molecular Structure of CPMPP molecule

Vol18No1_Ult_Roh_fig1
Click on image to enlarge

 Table 2: Optimized Bond Lengths of CPMPPmolecule obtained at B3LYP/6-31G(d.p)

Bond lengths (Å)

C1-C2

1.4038

C14-C17

1.4615

C1-C6

1.4033

C17-C18

1.4068

C1-O27

1.359

C17-C19

1.4086

C2-C3

1.3865

C18-C20

1.392

C2-H7

1.0847

C18-H21

1.0863

C3-C4

1.4077

C19-C22

1.3892

C3- H8

1.0843

C19-H23

1.0851

C4- C5

1.4028

C20-C24

1.3935

C4-C11

1.4941

C20-H25

1.0841

C5- C6

1.3902

C22-C24

1.3972

C5- H9

1.0846

C22-H26

1.0842

C6- H10

1.0833

C24-Cl28

1.7559

C11-C12

1.4871

O27-C29

1.422

C11-O16

1.2314

C29-H30

1.0968

C12-H13

C12-C14

       C14-H15      

1.084

1.3472

1.0889

C29-H31

C29-H32

1.0905

1.0968

Table 3: Optimized Bond Angles of CPMPPmolecule obtained at B3LYP/6-31(d,p)

Bond Angles (o)

C2-C1-C6

119.6544

H15-C14-C17

116.1539

C2-C1-O27

115.6855

C14-C17-C18

118.6637

C6-C1-O27

124.66

C14-C17-C19

123.5224

C1-C2-C3

120.158

C18-C17-C19

117.8139

C1-C2-H7

118.4593

C17-C18-C20

121.6314

C3-C2-H7

121.3826

C17-C18-H21

119.1249

C2-C3-C4

121.0568

C20-C18-H21

119.2437

C2-C3-H8

118.1341

C17-C19-C22

121.2893

C4-C3-H8

120.8024

C17-C19-H23

120.011

C3-C4-C5

117.9523

C22-C19-H23

118.6996

C3-C4-C11

124.4406

C18-C20-C24

118.9658

C5-C4-C11

117.6033

C18-C20-H25

120.8546

C4-C5-C6

121.7417

C24-C20-H25

120.1795

C4-C5-H9

117.7734

C19-C22-C24

119.3094

C6-C5-H9

120.4849

C19-C22-H26

120.7342

C1-C6-C5

119.4349

C24-C22-H26

119.9564

C1-C6-H10

120.9931

C20-C24-C22

120.9901

C5-C6-H10

119.572

C20-C24-Cl28

119.6102

C4-C11-C12

119.3039

C22-C24-Cl28

119.3997

C4-C11-O16

120.1517

C1-O27-C29

118.5306

C12-C11-O16

120.5424

O27-C29-H30

111.5468

C11-C12-H13

119.0571

O27-C29-H31

105.8923

C11-C12-C14

119.8758

O27-C29-H32

111.551

H13-C12-C14

121.0615

H30-C29-H31 

109.2772

C12-C14-H15

115.8011

H30-C29-H32

109.2239

C12-C14-C17

128.045

Global descriptors study

The pictorial representation of HOMO-LUMO orbitals is given in Figure 2. The electronic parameters such as EHOMO, ELUMO, ionization enthalpy (I), and electron affinity (A) are given in Table 4. The quantum chemical parameters likeelectronegativity (χ), absolute hardness (η), softness (σ), electrophilicity (ω), chemical potential (Pi) are presented in Table 5. The frontier molecular orbital (FMO) analysis suggests that the energy gap in the molecule CPMPP is 4.06 eV. The lower HOMO-LUMO energy gap demonstrates the inevitable charge transfer is happening within the molecule. The global softness (σ), and the absolute hardness (η) values are 0.4926and 2.03 eV respectively. The ease of removal of an electron is governed by its chemical potential Pi and it is likewise identified with its electronegativity (χ). A good electrophile is described by a higher value of global electrophilicity (ω) and the higher value of ω indicates good nucleophile. Our results suggest that the molecule CPMPP has a higher value of global electrophilicity (ω = 4.2625eV), so it is most likely to accept electrons readily and also would undergo nucleophilic attack easily. As Pi value increases, the ability of a molecule to lose an electron increases. The maximum charge transfer is in the title molecule is 2.0493eV.

Figure 2: HOMO-LUMO pictures of CPMPP molecule

Vol18No1_Ult_Roh_fig2
Click on image to enlarge

 Table 4: Electronic parameters of CPMPP molecule

Entry

E

(a.u.)

EHOMO

(eV)

ELUMO

(eV)

I

(eV)

A

(eV)

Eg

(eV)

 CPMPP

-1228.18

-6.19

-2.13

6.19

2.13

4.06

Table 5: Global reactivity parameters of CPMP Pmolecule.

Entry

χ

(eV)

ɳ

(eV)

σ

(eV-1)

ω

(eV)

Pi

(eV)

ΔNmax

(eV)

Dipole Moment (Debye)

CPMPP

4.16

2.03

0.4926

4.2625

-4.16

2.0493

3.1533

UV-Visible Analysis

The absorption energies (λ in nm), oscillator strength (ƒ) and electronic transitions of the CPMP Pmolecule were computed at the TD-DFT-B3LYP/6-31G(d,p) level of theory for the optimized structure. The absorption energies (λ in nm), oscillator strength (ƒ) and transitions of CPMP Pmolecule and experimental UV-Vis spectral analysis are given in Table 6. The theoretical UV-Vis absorption results were simulated up to three singlet excited states. The experimental UV-Vis spectra were recorded in the DCM solvent. Likewise, the theoretical UV-Vis spectra were computed in the gas phase, and the DCM solvent. The theoretical and experimental UV-Vis spectral images are depicted in Figure 3 and Figure4. The first singlet state (S1) is found to be at 382.50 nm in the gas phase and 368.76 nm in DCM. The experimental UV-visible absorption band is centred at 375.02nm in DCM solvent. This result suggests that the theoretical UV-Vis absorption results are in acceptable concurrence with the UV-Vis absorption experimental results. The HOMO-LUMO electronic transition corresponds to the 71 -> 72 configurations. The solvent effect on the HOMO-LUMO absorption wavelength of the DPPPM molecule is found to be a blue shift (hypsochromic shift) as per the UV-Vis absorption theoretical data. The second singlet excited state (S2) is present at 338.93nm (gas phase) and 350.05 nm (DCM) in the theoretical UV-Vis absorption spectrum. The second gas phase singlet excited state and also DCMO is composed of only oneconfiguration, namely 71 -> 72 configurations. The third gas phase singlet excited state (S3) is from 69 -> 72, 70 -> 72, and 71 -> 73 and 69 -> 72, 70 -> 72 in DCM. The third absorption band is located at 307.68 nm (gas phase) and 315.08 nm (DCM).

Figure 3: Experimental UV-Visible spectra in DCM

Vol18No1_Ult_Roh_fig3
Click on image to enlarge

Figure 4: Simulated UV-Visible spectra in gas phase and DCM of CPMPP molecule

Vol18No1_Ult_Roh_fig4
Click on image to enlarge

 Table 6 :Absorption wavelength (λ in nm), coefficient, oscillator strength (ƒ), and electronic transitions of titled compound computed at TD-DFT B3LYP/6-31G(d,p) level of theory (Experimental value of absorption wavelength (λ in nm) given in bracket).

Gas Phase

DCM

State

Config

Coefficient

f

λ, nm

Config

Coefficient

f

λ, nm

I

69 -> 72         69 -> 73         70 -> 72       

0.67881

0.10098

-0.12390

0.0002 

382.50

69 -> 72        

70 -> 72       

0.68263

0.10238

0.0019 

368.76

(375.02)

II

71 -> 72        

0.70176

0.6207 

338.93

71 -> 72        

0.70087

0.8907 

350.05

III

69 -> 72         70 -> 72        

71 -> 73       

0.12029

0.67825

-0.10067

0.4056 

307.68

69 -> 72         70 -> 72        

 

-0.10306

 

0.68537

 

 

0.2899 

315.08

Config- Configuration

Vibrational study

The experimental and theoretical IR spectrum of the title compound is given in Figure 5. In the given spectra, scaled theoretical IR values and experimental IR values are depicted. The comparison between the experimental and scaled IR values has led to the correct assignment of the vibrational bands. The CPMPP molecule consists of 32 atoms with 90 normal modes of vibration. Because of the anharmonicity of the incomplete treatment of electron correlation and the use of a finite one-particle basis set, computed harmonic vibrational wavenumbers are usually higher than experimental ones 55. B3LYP method was used to calculate harmonic frequencies using 6-31G(d,p) basis sets, which were then scaled by  appropriate scaling factor 56. The BLYP/6-31G(d,p) method produced better results, with a deviation from the experiment of less than 30 cm-1.

The aromatic C-H vibrational stretching is located at 3047 cm-1 in the in the experimental IR spectrum and at 3020 cm-1 theoretically predicted IR spectrum. This definitely suggests a great deal of agreement between the two compared values. The C=C stretching vibrations is observed at 1601 cm-1 and 1597 cm-1 in the experimental and theoretical IR spectra respectively. The another important C=C vibration was found at 1489 cm-1 and 1473 cm-1 in the experimental and theoretical IR spectra respectively. The C-H bending vibrations are found at 1327 cm-1 and 1308 cm-1 in the experimental and theoretical IR spectra respectively. The C-O stretching vibration is found at 1211 cm-1 in the experimental IR spectrum and at1194 cm-1 in the theoretical IR spectrum. The 1087 cm-1 in the experimental and 1108 in the experimental are attributed to C-C stretching vibrations. The experimental 995 cm-1 matches with the theoretical 1002 cm-1 is occurred due to the bending vibrational mode.Throughout this regard, the correlation was used to correctly assign vibrational bands to the title compounds, and the IR spectra of the titled compound have a very strong correlation.

Figure 5: Combined experimental and theoretical IR spectra showing selected vibrational assignments of CPMPP molecule

Vol18No1_Ult_Roh_fig5
Click on image to enlarge

 Mulliken Atomic Charges and Molecular Electrostatic Plot Analysis

The Mulliken atomic charges of the CPMPP molecule are calculated by DFT/B3LYP method with 6-31G(d,p) basis set in the gaseous phase and are given in Table 7. Mulliken atomic charges reveal that all the hydrogen atoms have a net positive charge but H15 and H31 atoms have a more positive charge than other hydrogen atoms and therefore they are more acidic. Amongst, carbon atoms, the C11 atom have the highest net positive charge (0.372919) as it is attached to an electronegative oxygen atom. On the other hand C12 atom has the highest negative charge (-0.141075).

Table 7: Mulliken atomic chargesof CPMPP

Atom

Charge

Atom

Charge

1  C

0.362574

17  C

0.127545

2  C

-0.128205

18  C

-0.123597

3  C

-0.112476

19  C

-0.105209

4  C

0.038662

20  C

-0.073641

5  C

-0.107676

21  H

0.104888

6  C

-0.137000

22  C

-0.074632

7  H

0.098792

23  H

0.094380

8  H

0.087747

24  C

-0.093211

9  H

0.120507

25  H

0.115548

10  H

0.092396

26  H

0.114129

11  C

0.372919

27  O

-0.512859

12  C

-0.141075

28 Cl

-0.013042

13  H

0.081235

29 C

-0.083420

14 C

-0.090049

30 H

0.118400

15 H

0.122194

31 H

0.129564

16 O 

-0.503478

32 H

0.118091

Figure 6 shows the molecular electrostatic potential plot. The use of a molecular electrostatic potential can be used to evaluate phenomena such as nucleophilic and electrophilic positions, solvent effects, hydrogen bonding interactions, and so on. MEP is mainly used to establish the reactive sites of molecules, enabling researchers to predict how one particle will interact with another. The various electrostatic potential values at the molecule’s surface are expressed by different colours. Electrophilic reactivity is correlated with the red and yellow zones, which lead to high electron density. The blue sections, on the other hand, reflect low electron density and nucleophilic reactivity, while the green colours represent regions of zero potential.

Figure 6: Molecular electrostatic potential

Vol18No1_Ult_Roh_fig6
Click on image to enlarge

Conclusion

Present investigation deals with the synthesis and DFT study of a chalcone derivative; (E)-3-(4-chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one. The synthesis of a CPMPP has been carried out by the reaction of 4-methoxyacetophenone and 4-chlorobenzalehyde in ethanol at 30℃ under ultrasound irradiation. The structure of a synthesized chalcone is affirmed on the basis of FT-IT, 1H NMR and 13C NMR. The geometry of a CPMPP is optimized by using the density functional theory method at the B3LYP/6-31G(d,p) basis set. The molecule CPMPP is having C1 point group symmetry and the dipole moment is 3.1533 Debye. The optimized geometrical parameters like bond length and bond angles have been computed. The quantum chemical parameters likeelectronegativity, absolute hardness, softness, electrophilicity, chemical potential are presented. The FMO analysis suggests that the energy gap in the molecule CPMPP is 4.06 eV. The lower HOMO-LUMO energy gap demonstrates the inevitable charge transfer is happening within the molecule.The absorption energies, oscillator strength, and electronic transitions have been derived at the TD-DFT method at the B3LYP/6-31G(d,p) level of theory for B3LYP/6-31G(d p) optimized geometries. The effect of polarity on the absorption energies is discussed by computing UV-visible results in DCM. The solvent effect on the HOMO-LUMO absorption wavelength of the CPMPP molecule is found to be a blue shift as per the UV-Vis absorption theoretical data. Mulliken atomic charges reveal that all the hydrogen atoms have a net positive charge but H15 and H31 atoms have a more positive charge than other hydrogen atoms and therefore they are more acidic. Amongst, carbon atoms, the C11 atom have the highest net positive charge (0.372919) as it is attached to an electronegative oxygen atom. On the other hand C12 atom has the highest negative charge (-0.141075).

Acknowledgment

Author acknowledges Department of Chemistry, Arts, Science and Commerce College, Manmad, MS, India for the research assistance. Authoris grateful to Prof. (Dr.) T. B. Pawar for his guidance for the Gaussian study.

Funding Sourse 

No funding was received to carry out the present research.

References

  1. MT Albuquerque, H., MM Santos, C., AS Cavaleiro, J. and MS Silva, A., 2014. Chalcones as Versatile Synthons for the Synthesis of 5-and 6-membered Nitrogen Heterocycles. Current Organic Chemistry18(21), pp.2750-2775.
    CrossRef
  2. Velikorodov, A.V., Ionova, V.A., Temirbulatova, S.I., Titova, O.L. and Stepkina, N.N., 2013. Synthesis and application of chalcones to the preparation of heterocyclic structures. Russian journal of organic chemistry49(11), pp.1610-1616.
    CrossRef
  3. Rostom, S.A., Badr, M.H., Abd El Razik, H.A., Ashour, H.M. and Abdel Wahab, A.E., 2011. Synthesis of some pyrazolines and pyrimidines derived from polymethoxy chalcones as anticancer and antimicrobial agents. Archiv der Pharmazie344(9), pp.572-587.
    CrossRef
  4. Adel, A.H., Ahmed, E.S., Hawata, M.A., Kasem, E.R. and Shabaan, M.T., 2007. Synthesis and Antimicrobial Evaluation of Some Chalcones and Their Derived Pyrazoles, Pyrazolines, Isoxazolines, and 5,6-Dihydropyrimidine-2-(1H)-thiones. Monatshefte für Chemie-Chemical Monthly138(9), pp.889-897.
    CrossRef
  5. Chobe, S.S., Adole, V.A., Deshmukh, K.P., Pawar, T.B. and Jagdale, B.S., 2014. Poly (ethylene glycol)(PEG-400): A green approach towards synthesis of novel pyrazolo [3, 4-d] pyrimidin-6-amines derivatives and their antimicrobial screening. Archives of Applied Science Research6(2), pp.61-66.
  6. Cui, M., Ono, M., Kimura, H., Liu, B.L. and Saji, H., 2011. Synthesis and biological evaluation of indole-chalcone derivatives as β-amyloid imaging probe. Bioorganic & medicinal chemistry letters21(3), pp.980-982.
    CrossRef
  7. Sun, L.P., Jiang, Z., Gao, L.X., Sheng, L., Quan, Y.C., Li, J. and Piao, H.R., 2013. Synthesis and biological evaluation of furan-chalcone derivatives as protein tyrosine phosphatase inhibitors. Bulletin of the Korean Chemical Society34(4), pp.1023-1024.
    CrossRef
  8. Dandawate, P., Ahmed, K., Padhye, S., Ahmad, A. and Biersack, B., 2021. Anticancer Active heterocyclic chalcones: recent developments. Anti-Cancer Agents in Medicinal Chemistry (Formerly Current Medicinal Chemistry-Anti-Cancer Agents)21(5), pp.558-566.
    CrossRef
  9. Kuete, V., Nkuete, A.H., Mbaveng, A.T., Wiench, B., Wabo, H.K., Tane, P. and Efferth, T., 2014. Cytotoxicity and modes of action of 4′-hydroxy-2′, 6′-dimethoxychalcone and other flavonoids toward drug-sensitive and multidrug-resistant cancer cell lines. Phytomedicine21(12), pp.1651-1657.
    CrossRef
  10. Adole, V.A., Pawar, T.B. and Jagdale, B.S., 2020. Aqua‐mediated rapid and benign synthesis of 1,2,6,7‐tetrahydro‐8H‐indeno [5,4‐b] furan‐8‐one‐appended novel 2‐arylidene indanones of pharmacological interest at ambient temperature . Journal of the Chinese Chemical Society67(2), pp.306-315.
    CrossRef
  11. Chiaradia, L.D., Dos Santos, R., Vitor, C.E., Vieira, A.A., Leal, P.C., Nunes, R.J., Calixto, J.B. and Yunes, R.A., 2008. Synthesis and pharmacological activity of chalcones derived from 2, 4, 6-trimethoxyacetophenone in RAW 264.7 cells stimulated by LPS: Quantitative structure–activity relationships. Bioorganic & medicinal chemistry16(2), pp.658-667.
    CrossRef
  12. Batovska, D.I. and Todorova, I.T., 2010. Trends in utilization of the pharmacological potential of chalcones. Current clinical pharmacology5(1), pp.1-29.
    CrossRef
  13. Nowakowska, Z., 2007. A review of anti-infective and anti-inflammatory chalcones. European journal of medicinal chemistry42(2), pp.125-137.
    CrossRef
  14. K Sahu, N., S Balbhadra, S., Choudhary, J. and V Kohli, D., 2012. Exploring pharmacological significance of chalcone scaffold: a review. Current medicinal chemistry19(2), pp.209-225.
    CrossRef
  15. Matos, M.J., Vazquez-Rodriguez, S., Uriarte, E. and Santana, L., 2015. Potential pharmacological uses of chalcones: a patent review (from June 2011–2014). Expert opinion on therapeutic patents25(3), pp.351-366.
    CrossRef
  16. Syam, S., Abdelwahab, S.I., Al-Mamary, M.A. and Mohan, S., 2012. Synthesis of chalcones with anticancer activities .   Molecules17(6), pp.6179-6195.
    CrossRef
  17. Anto, R.J., Sukumaran, K., Kuttan, G., Rao, M.N.A., Subbaraju, V. and Kuttan, R., 1995. Anticancer and antioxidant activity of synthetic chalcones and related compounds. Cancer letters97(1), pp.33-37.
    CrossRef
  18. Won, S.J., Liu, C.T., Tsao, L.T., Weng, J.R., Ko, H.H., Wang, J.P. and Lin, C.N., 2005. Synthetic chalcones as potential anti-inflammatory and cancer chemopreventive agents. European journal of medicinal chemistry40(1), pp.103-112.
    CrossRef
  19. Lahtchev, K.L., Batovska, D.I., St P, P., Ubiyvovk, V.M. and Sibirny, A.A., 2008. Antifungal activity of chalcones: A mechanistic study using various yeast strains. European journal of medicinal chemistry43(10), pp.2220-2228.
    CrossRef
  20. Trivedi, J.C., Bariwal, J.B., Upadhyay, K.D., Naliapara, Y.T., Joshi, S.K., Pannecouque, C.C., De Clercq, E. and Shah, A.K., 2007. Improved and rapid synthesis of new coumarinyl chalcone derivatives and their antiviral activity. Tetrahedron Letters48(48), pp.8472-8474.
    CrossRef
  21. Ávila, H.P., Smânia, E.D.F.A., Delle Monache, F. and Júnior, A.S., 2008. Structure–activity relationship of antibacterial chalcones. Bioorganic & medicinal chemistry16(22), pp.9790-9794.
    CrossRef
  22. Boumendjel, A., Boccard, J., Carrupt, P.A., Nicolle, E., Blanc, M., Geze, A., Choisnard, L., Wouessidjewe, D., Matera, E.L. and Dumontet, C., 2008. Antimitotic and antiproliferative activities of chalcones: forward structure–activity relationship. Journal of medicinal chemistry51(7), pp.2307-2310.
    CrossRef
  23. Kumar, D., Kumar, N.M., Akamatsu, K., Kusaka, E., Harada, H. and Ito, T., 2010. Synthesis and biological evaluation of indolyl chalcones as antitumor agents. Bioorganic & medicinal chemistry letters20(13), pp.3916-3919.
    CrossRef
  24. Li, R., Kenyon, G.L., Cohen, F.E., Chen, X., Gong, B., Dominguez, J.N., Davidson, E., Kurzban, G., Miller, R.E., Nuzum, E.O. and Rosenthal, P.J., 1995. In vitro antimalarial activity of chalcones and their derivatives. Journal of medicinal chemistry38(26), pp.5031-5037.
    CrossRef
  25. Rammohan, A., Bhaskar, B.V., Venkateswarlu, N., Gu, W. and Zyryanov, G.V., 2020. Design, synthesis, docking and biological evaluation of chalcones as promising antidiabetic agents. Bioorganic chemistry95, p.103527.
    CrossRef
  26. Parmar, S.S., Pandey, B.R., Dwivedi, C. and Harbison, R.D., 1974. Anticonvulsant activity and monoamine oxidase inhibitory properties of 1, 3, 5‐trisubstituted pyrazolines. Journal of pharmaceutical sciences63(7), pp.1152-1155.
    CrossRef
  27. El-Borai, M.A., Rizk, H.F., Sadek, M.R. and El-Keiy, M.M., 2016. An eco-friendly synthesis of heterocyclic moieties condensed with pyrazole system under green conditions and their biological activity. Green and Sustainable Chemistry6(2), pp.88-100.
    CrossRef
  28. Shinde, R.A., Adole, V.A., Jagdale, B.S. and Pawar, T.B., 2020. Experimental and Theoretical Studies on the Molecular Structure, FT-IR, NMR, HOMO, LUMO, MESP, and Reactivity Descriptors of (E)-1-(2,3-Dihydrobenzo [b][1,4] dioxin-6-yl)-3-(3,4,5-trimethoxyphenyl) prop-2-en-1-one. Material Science Research India17(specialissue2020), pp.54-72.
    CrossRef
  29. Abbass, E.M., Khalil, A.K. and El‐Naggar, A.M., 2020. Eco‐friendly synthesis of novel pyrimidine derivatives as potential anticancer agents. Journal of Heterocyclic Chemistry57(3), pp.1154-1164.
    CrossRef
  30. Adole, V.A., Waghchaure, R.H., Pathade, S.S., Patil, M.R., Pawar, T.B. and Jagdale, B.S., 2020. Solvent-free grindstone synthesis of four new (E)-7-(arylidene)-indanones and their structural, spectroscopic and quantum chemical study: a comprehensive theoretical and experimental exploration. Molecular Simulation46(14), pp.1045-1054.
    CrossRef
  31. Rayudu, S.V., Karmakar, D. and Kumar, P., 2019. Water-acetic acid mediated an efficient one-pot eco-friendly synthesis of novel bis-isoxazolopyrroloquinoline derivatives. Tetrahedron Letters60(36), p.151025.
    CrossRef
  32. Shinde, R.A., Adole, V.A., Jagdale, B.S., Pawar, T.B., Desale, B.S. and Shinde, R.S., 2020. Efficient Synthesis, Spectroscopic and Quantum Chemical Study of 2, 3-Dihydrobenzofuran Labelled Two Novel Arylidene Indanones: A Comparative Theoretical Exploration. Material Science Research India17(2), pp.146-161.
    CrossRef
  33. Pourshojaei, Y., Jadidi, M.H., Eskandari, K., Foroumadi, A. and Asadipour, A., 2018. An eco-friendly synthesis of 4-aryl-substituted pyrano-fuzed coumarins as potential pharmacological active heterocycles using molybdenum oxide nanoparticles as an effective and recyclable catalyst. Research on Chemical Intermediates44(7), pp.4195-4212.
    CrossRef
  34. Adole, V.A., Pawar, T.B., Koli, P.B. and Jagdale, B.S., 2019. Exploration of catalytic performance of nano-La2O3 as an efficient catalyst for dihydropyrimidinone/thione synthesis and gas sensing. Journal of Nanostructure in Chemistry9(1), pp.61-76.
    CrossRef
  35. Adole, V.A., More, R.A., Jagdale, B.S., Pawar, T.B. and Chobe, S.S., 2020. Efficient synthesis, antibacterial, antifungal, antioxidant and cytotoxicity study of 2‐(2‐hydrazineyl) thiazole derivatives. ChemistrySelect5(9), pp.2778-2786.
    CrossRef
  36. Uludağ, N. and Serdaroğlu, G., 2018. An improved synthesis, spectroscopic (FT-IR, NMR) study and DFT computational analysis (IR, NMR, UV–Vis, MEP diagrams, NBO, NLO, FMO) of the 1, 5-methanoazocino [4, 3-b] indole core structure. Journal of Molecular Structure1155, pp.548-560.
    CrossRef
  37. Adole, V.A., 2020. Synthetic approaches for the synthesis of dihydropyrimidinones/thiones (biginelli adducts): a concise review. World Journal of Pharmaceutical Research9(6), pp.1067-1091.
  38. Kaviani, S., Izadyar, M. and Housaindokht, M.R., 2016. Solvent and spin state effects on molecular structure, IR spectra, binding energies and quantum chemical reactivity indices of deferiprone–ferric complex: DFT study. Polyhedron117, pp.623-627.
    CrossRef
  39. Dhonnar, S.L., Adole, V.A., Sadgir, N.V. and Jagdale, B.S., 2021. Structural, Spectroscopic (UV-Vis and IR), Electronic and Chemical Reactivity Studies of (3, 5-Diphenyl-4, 5-dihydro-1H-pyrazol-1-yl)(phenyl) methanone. Physical Chemistry Research9(2), pp.193-209.
    CrossRef
  40. Sheikhi, M., Shahab, S., Khaleghian, M., Hajikolaee, F.H., Balakhanava, I. and Alnajjar, R., 2018. Adsorption properties of the molecule resveratrol on CNT (8, 0-10) nanotube: geometry optimization, molecular structure, spectroscopic (NMR, UV/Vis, excited state), FMO, MEP and HOMO-LUMO investigations. Journal of Molecular Structure1160, pp.479-487.
    CrossRef
  41. Adole, V.A., Waghchaure, R.H., Jagdale, B.S. and Pawar, T.B., 2020. Investigation of Structural and Spectroscopic Parameters of Ethyl 4-(4-isopropylphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate: a DFT Study. Chemistry & Biology Interface10(1).
  42. Ramazani, Ali, Masoome Sheikhi, and Hooriye Yahyaei. “Molecular Structure, NMR, FMO, MEP and NBO Analysis of Ethyl-(Z)-3-phenyl-2-(5-phenyl-2H-1, 2, 3, 4-tetraazol-2-yl)-2-propenoate Based on HF and DFT Calculations.” Chemical Methodologies 1, no. 1 (2017): 28-48.
    CrossRef
  43. Adole, V.A., Jagdale, B.S., Pawar, T.B. and Desale, B.S., 2020. Molecular structure, frontier molecular orbitals, MESP and UV–visible spectroscopy studies of Ethyl 4-(3,4-dimethoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate: A theoretical and experimental appraisal. Material Science Research India17(specialissue2020), pp.13-36.
    CrossRef
  44. Pathade, S.S. and Jagdale, B.S., 2020. Experimental and Computational Investigations on the Molecular Structure, Vibrational Spectra, Electronic Properties, FMO and MEP Analyses of 4, 6-Bis (4-Fluorophenyl)-5, 6-dihydropyrimidin-2 (1H)-one: A DFT Insight. Physical Chemistry Research8(4), pp.671-687.
  45. Wang, Y., Liu, Q., Qiu, L., Wang, T., Yuan, H., Lin, J. and Luo, S., 2015. Molecular structure, IR spectra, and chemical reactivity of cisplatin and transplatin: DFT studies, basis set effect and solvent effect. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy150, pp.902-908.
    CrossRef
  46. Adole, V.A., Waghchaure, R.H., Jagdale, B.S., Pawar, T.B. and Pathade, S.S., Molecular tructure, frontier molecular orbital and spectroscopic examination on dihydropyrimidinones: a comparative computational approach Journal of Advanced Scientific Research, 2020. 11 (2), pp.64-70.
  47. Mebi, C.A., 2011. DFT study on structure, electronic properties, and reactivity of cis-isomers of [(NC5H4-S)2Fe(CO)2]. Journal of Chemical Sciences123(5), pp.727-731.
    CrossRef
  48. Adole, V.A., Pawar, T.B. and Jagdale, B.S., 2021. DFT computational insights into structural, electronic and spectroscopic parameters of 2-(2-Hydrazineyl) thiazole derivatives: a concise theoretical and experimental approach. Journal of Sulfur Chemistry,42(2) pp. 131-148.
    CrossRef
  49. Adole, V.A., Koli, P.B., Shinde, R.A. and Shinde, R.S., 2020. Computational Insights on Molecular Structure, Electronic Properties, and Chemical Reactivity of (E)-3-(4-Chlorophenyl)-1-(2-Hydroxyphenyl) Prop-2-en-1-one. Material Science Research India17(specialissue2020), pp.41-53.
    CrossRef
  50. Pathade, S.S., Adole, V.A., Jagdale, B.S. and Pawar, T.B., 2020. Molecular structure, electronic, chemical and spectroscopic (UV-visible and IR) studies of 5-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazole: combined DFT and experimental exploration. Material Science Research India17(specialissue2020), pp.27-40.
  51. Adole, V.A., Jagdale, B.S., Pawar, T.B. and Sawant, A.B., 2020. Experimental and theoretical exploration on single crystal, structural, and quantum chemical parameters of (E)‐7‐(arylidene)‐1,2,6,7‐tetrahydro‐8H‐indeno[5,4‐b] furan‐8‐one derivatives: A comparative study. Journal of the Chinese Chemical Society67(10), pp.1763-1777.
    CrossRef
  52. Pawar, T.B., Jagdale, B.S., Sawant, A.B. and Adole, V.A., 2017. DFT Studies of 2-[(2-substitutedphenyl) carbamoyl] benzoic acids. Journal of Chemical, Biological and Physical Sciences7, pp.167-175.
  53. Adole,V.A., Bagul, V.R., Ahire, S.A., Pawar, R.K., Yelmame, G.B.,and Bukane, A.R.,2021. Computational chemistry: molecular structure, spectroscopic (UV-visible and IR), electronic, chemical and thermochemical analysis of 3′-phenyl-1,2- dihydrospiro[indeno[5,4-b], Journal of Advanced Scientific Research, 12(1) Suppl 1, pp. 276-286.
  54. Frisch, M., Trucks, G., Schlegel, H., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery Jr, J.A., Vreven, T.K.K.N., Kudin, K.N., Burant, J.C. and Millam, J.M., 2004. Gaussian 03, revision C. 02.
  55. Szafran, M., Katrusiak, A., Koput, J. and Dega-Szafran, Z., 2007. X-ray, MP2 and DFT studies of the structure, vibrational and NMR spectra of homarine. Journal of Molecular Structure846(1-3), pp.1-12.
    CrossRef
  56. Dereli, Ö., Sudha, S. and Sundaraganesan, N., 2011. Molecular structure and vibrational spectra of 4-phenylsemicarbazide by density functional method. Journal of Molecular Structure994(1-3), pp.379-386.
    CrossRef
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