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Synthesis, Spectroscopic Characterization, Quantum Chemical Study and Antimicrobial Study of (2e) -3-(2, 6-Dichlorophenyl) -1-(4-Fluoro) -Prop-2-En-1-One

Nutan V.Sadgir1 *, Sunil L.Dhonnar1, Bapu Jagdale2,  Bhagyashri Waghmare3 and Chetan Sadgir4

1Department of Chemistry, L.V.H. Arts, Science, and Commerce  College, Panchavati, Nashik (M.S) India.

2Department of Chemistry, Arts, Science, and Commerce  College, Manmad, Nashik (M.S) India.

3Department of Chemistry M.S.G. Arts, Science and Commerce College,Malegaon,Nashik(M.S.) India

4Zydus Cadila Ahmedabad,Gujrat,India

Corresponding Author Email: nutansadgir@gmail.com

DOI : http://dx.doi.org/10.13005/msri/170311

Article Publishing History
Article Received on : 10-September-2020
Article Accepted on : 19-Nov-2020
Article Published : 23 Nov 2020
Plagiarism Check: Yes
Reviewed by: Sapana Jadoun 
Second Review by: Rizwan Arif 
Final Approval by: Ramachandra Naik 
Article Metrics
ABSTRACT:

In the present work (2E) -3-(2, 6-dichlorophenyl) -1-(4-Fluoro) -prop-2-en-1-one  was Prepared  by Claisen-Schmidt condensation .Synthesized molecules were characterized by using FTIR, 1H NMR spectroscopy.Molecular geometry,Vibrational frequency of title compound were calculated using the DFT/B3LYP method with 6-311++G (d, p) basis set.The experimentally obtained FTIR spectra were in good agreement with calculated infrared spectrum.The FMO and molecular electrostatic potentialwere performed to study the reactivity of molecules at the same levelof theory. The synthesized compound shows moderate antimicrobial activity

KEYWORDS: Chalcone; DFT; FMO; Gaussian-03; UV-Visible

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Sadgir N. V, Dhonnar S. L, Jagdaleb B, Waghmare B, Sadgird C, Synthesis, Spectroscopic characterization, Quantum Chemical studyand antimicrobial study of (2E) -3-(2, 6-dichlorophenyl) -1-(4-Fluoro) -prop-2-en-1-one.Mat. Sci. Res. India; 17(3).

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Sadgir N. V, Dhonnar S. L, Jagdaleb B, Waghmare B, Sadgird C, Synthesis, Spectroscopic characterization, Quantum Chemical studyand antimicrobial study of (2E) -3-(2, 6-dichlorophenyl) -1-(4-Fluoro) -prop-2-en-1-one.Mat. Sci. Res. India; 17(3). Available from: https://bit.ly/3pVfLcD

Introduction

The Chalcone is a simple scaffold found in many naturally occurring compounds mainly in flavonoids and isoflavonoids in plants or can be synthesized in laboratory by different methods. Basically chalcones are alpha, beta unsaturated ketone, in which two aromatic rings joined at 1 and 3 position (1,3-diphenyl-2E-propene-2-one).The two rings of chalcones are interconnected  by electrophilic nature of alpha beta unsaturated carbonyl system, which are having complete delocalisation on both aromatic rings. It exists as cis and trans isomer in which trans isomer is thermodynamically more stable. They display a wide range of pharmacological activities   like antimicrobial[4,5], antifungal [6] anticancer [7],antileishmanial [8],anti-HIV [9], anti-inflammatory [10], anti-tuberculosis [11] ,anticonvulsant [12] , ant-viral [13],anti-oxidant [14], anti-diabetic [15] etc.Chalcone act as a unique template for synthesis of different heterocyclic like Pyrazoline, Oxazolines, pyrimidinesetc.

Density Functional Theory has been very popular in describing the structural and electronic properties of atoms and molecules. The main objective of this paper to synthesized title compound and study their experimental and computational investigation on the Molecular structure, vibrational spectra, and electronic properties. We have  synthesized of 2E)-3-(2, 6-dichlorophenyl)-1-(4-Fluoro)-prop-2-en-1-one by Claisen-Schmidt condensation and study their molecular structure, and Vibrational Frequencies investigation by DFT at B3LYP/6-311++G(d,p) level, In addition to this FMOs, ionization potential, electronegativity, global Electrophilicity index, chemical potential were studied by using a 6-311++G (d, p) basis set.

Experimental

Material and Physical Measurement

The Chemicals used for synthesis are of AR grade.Melting point of the compound was determinedin an open capillaries and uncorrected.FTIR spectrum of title compound was recorded on Shimadzu spectrometer using KBr pellets. The 1H NMR was recordedon Brucker Avance 500MHZ spectrometer using TMS as an internal standard. Reaction is monitored by thin layer chromatography by using n-hexane and ethyl acetate solvent system.

Synthesis of (2E) -3-(2, 6-dichlorophenyl) -1-(4-4-Fluoro) -prop-2-en-1-one

The 4-Fluoroacetophenone (0.01 mole) and 2, 6dichloro benzaldehyde (0.01 mole) were dissolved in ethyl alcohol and 5ml of KOH (20%) was added drop wise to the solution with stirring at room temperature. The completion of the reaction was monitored by TLC. After completion of reaction, reaction mixture poured into crushed ice and acidified with dil. HCl.The solid compound obtained was filtered, driedand recrystallized from ethyl alcohol.

Yield: 87%, FT-IR (KBr,cm-1): 3076(aromatic C-H), 2839(C-H), 1664 (C=O), 1602 (C=C),1508 (aromatic C=C), ; 1H NMR (500 MHz,CDCl3,δ/ppm): 8.05 (d, J= 8.5 Hz.2H), 7.84 (d,J = 16 Hz,1H), 7.63(d, J =16 Hz,1H), 7.387 (d,J =8 Hz,2H), 7.170-7.237  (m,3H).

Scheme 1: Synthesis of (2E) -3-(2, 6-dichlorophenyl) -1-(4-4-Fluoro) -prop-2-en-1-one

Scheme 1: Synthesis of (2E) -3-(2, 6-dichlorophenyl) -1-(4-4-Fluoro) -prop-2-en-1-one
Click on image to enlarge

Computational Details

The Density functional theory (DFT) calculations were performed on an Intel (R) Core (TM) i7 personal computer using Gaussian -03 program package[17]. Thegeometry of the title compound was optimized by DFT /B3LYF method with 6-311++G (d, p) basis set level [18-20]. To explore the electronic properties, the theoretical UV-Visible spectra have been investigated by the TD-DFT method with a 6-311++G (d, p) basis in the gas phase.

Figure 1: Optimized structure of title compound

Figure 1: Optimized structure of title compound
Click on image to enlarge

 Results and Discussion

Molecular Geometry

The optimize structure of the title compound with the labelling of atoms shown areFig.1 The molecular structure of the title compound contains two six membered rings in which, one is 2, 6-dichloro substituted ring attach to C=C of enone system (ring B) and another ring is a 4-Fluoro substituted ring attach to carbonyl group (ring A).The α, β-unsaturated ketone is confirmedby the shorter bond length O2-C20 and C6-C8 are found to be 1.223Å, 1.34Årespectively. The C 13-F28, Cl1-C23 and Cl2-C12 bond lengths are 1.352 Å, 1.757Å and 1.759Å respectively and foundwithin the normal range.Allthe bond lengths are within the normal range and compared with the previously reported structure [22-26].The calculated C 20-C6,C8-C5torsion angle is 179.50 confirms the molecule exhibits E configuration, which shows trans geometry.

Figure 2: Bond length of the title compound

Figure 2: Bond length of the title compound
Click on image to enlarge

Table 1: The bond length and dihedral angle of title compound calculated at B3LYP/6-311++G (d, p) level

Bond

Bond Length

[Å]

Bond

Bond Angle

[°]

Cl(1)-C(23)

1.757

Cl(1)-C(23)-C(5)

119.64

Cl(2)-C(12)

1.759

Cl(2)-C(12)-C(5)

121.39

O(3)-C(20)

1.223

O(3)-C(20)-C(4)

120.02

C(4)-C(20)

1.499

O(3)-C(20)-C(6)

120.8

C(4)-C(14)

1.404

C(4)-C(10)-C(26)

120.97

C(4)-C(10)

1.402

C(20)-C(4)-C(10)

123.9

C(5)-C(8)

1.470

H(9)-C(8)-C(6)

116.54

C(5)-C(23)

1.412

H(7)-C(6)-C(8)

120.99

C(5)-C(12)

1.411

H(7)-C(6)-C(20)

119.24

C(6)-C(20)

1.490

C(5)-C(8)-H(9)

115.86

C(6)-C(8)

1.340

C(5)-C(8)-C(6)

127.54

C(6)-H(7)

1.080

C(8)-C(6)-C(20)

119.76

C(8)-H(9)

1.086

C(20)-C(6)-H(7)

119.24

C(10)-C(26)

1.392

C(10)-C(4)-H(14)

118.59

C(10-H(11)

1.080

H(15)-C(14)-C(4)

118.21

C(12)-C(21)

1.391

H(15)-C(14)-C(16)

120.60

C(13)-C(16)

1.389

C(4)-C(14)-C(16)

121.19

C(13)-C(26)

1.385

C(14)-C(16)-H(17)

121.82

C(13)-F(28)

1.352

C(14)-C(16)-C(13)

118.33

C(14)-H(15)

1.083

C(16)-C(13)-F(28)

118.77

C(14)-H(16)

1.387

C(13)-C(16)-H(17)

119.84

C(16)-H(17)

1.083

F(28)-C(13)-C(26)

118.74

C(18)-H(19)

1.083

H(27)-C(26)-C(13)

119.90

C(18)-C(21)

1.390

H(27)-C(26)-C(10)

121.67

C(18)-C(24)

1.390

H(11)-C(10)-C(26)

117.99

C(21)-H(22)

1.082

C(5)-C(12)-C(21)

122.46

C(23)-C(24)

1.388

H(22)-C(21)-C(12)

119.38

C(24)-H(25)

1.082

H(22)-C(21)-C(18)

120.85

C(26)-H(27)

1.083

H(19)-C(18)-C(21)

119.91

 

 

H(19)-C(18)-C(24)

119.99

 

 

C(18)-C(24)-H(25)

121.12

 

 

C(23)-C(24)-H(25)

119.69

Figure 3: a) The Graphical representation of bond length and b) Bond Angle

Figure 3: a) The Graphical representation of bond length and b) Bond Angle
Click on image to enlarge

 

Vibrational frequencyAssignment  

Comparison of vibrational assignment of title compound by Experimental IR spectrum with theoretical IR spectrum. Experimental IR spectrum is recorded in the region of 4000-500 cm–1(Solid phase) and calculated vibrational spectrum in the gas phase. Title compound contains total 28 atoms with 78 fundamental modes of vibration. Theoretical and experimental IR spectrum is shown in Fig 4a and 4b.Carbonyl stretching frequency of alpha beta unsaturated ketone in the range of 1700-1600 cm-1, the experimental carbonyl stretching frequency of title compound 1658 cm-1 and theoretically it is 1664 cm-1 this confirms presence of carbonyl group, lower value of IR frequency is due to conjugation of enone system with the aromatic rings. Experimental IR at 1525cm-1 and theoretical IR at 1508cm-1 is due to the Ar-C=C- stretching  vibrations. Outof plane bending vibrations experimentally at 972.12 cm-1 and theoretically at 972cm-1shows  trans geometry of alkene. The C-H experimental and theoretical is stretching vibration 3076 cm-1 and 3072cm-1respectively.

Figure 4: a) Experimental FT-IR spectrum and b) Simulated IR spectrum of title compound

Figure 4: a) Experimental FT-IR spectrum and b) Simulated IR spectrum of title compound
Click on image to enlarge

Table 2: Selected Experimental and theoretical vibrational assignments of title compound.

Selected mode no

Calculated (Scaled) frequencies in cm-1

Calculated IR intensity

Experimental Frequencies cm-1

Assignment

78

3104

4.25

–

υsym (10)C-(11)H ring b+ υsym (6)C-(7)H(C=C)

77

3087

2.29

–

υsymCH (Ring a)

76

3085

5.50

–

υsym CH (Ring b)

75

3083

0.86

–

υsym CH (Ring b)

74

3082

0.24

–

υasymm (Ring a)

73

3072

0.189

3076

υasymm (Ring b) CH+ υsym (6)C-(7)H(C=C)

72

3070

5.17

–

υasymm (Ring b)

71

3061

2.64

–

υasymm (Ring a)

70

3042

1.69

–

(8)C- (9)H(C=C)

69

1656

136.31

1664.57

υ C=O

68

1590

289.29

1602.85

υ C=C,C=O

67

1572

129.83

–

υ C=C and CH (Ring b)

66

1560

19.88

–

υ C=C and CH (Ring b)

65

1554

18.02

–

υ C=C and CH (Ring a)

64

1525

33.85

1508

υ C=C and CH (Ring a)

63

1475

35.93

1498.69

υ C=C and CH (Ring b)

62

1405

42.57

1415.75

υ C=C and CH (Ring a)

60

1381

20.89

–

υ C=C and CH (Ring b)

59

1312

49.65

1300.02

υ C=C

58

1289

17.59

–

υ C=C and CH (Ring b)

55

1242

67.61

–

υ C=C (Ring a)

46

1048

2.56

1093.64

υ C=C and CH (Ring a)

45

992

53.00

1008.77

 υ C=C and CH (Ring b)

43

972

39.33

972.12

 υ γCH (C=C)

40

921

1.54

900.76

 υ CH (Ring a)

39

879

8.54

–

υ CH(C=C)

36

827

36.16

827.46

 υ CH (Ring a)

35

810

23.98

–

υ C-(28)F

34

794

1.83

–

υCH (Ring b)

33

760

3.36

771.53

 Υ CH (Ring b)

31

748

91.73

–

υ C-(1)Cl

v- stretching; asym-asymmetric; sym-symmetric; def-deformation; β-In-plane bending; γ-out of plane bending, ρ-rocking, Г-torsion

UV-Vis Spectra Study and Global Chemical Reactivity Parameters

The absorption energies (λ in nm), oscillator strength (ƒ), and electronic transitions of the title compound have been computed at the TD-DFT B3LYP/6-311++G (d, p) level of theory for optimized geometry. To study the effect of solvent on the wavelength of absorption, TD-DFT calculation, perform in both gas and DCM solvent. The calculated electronic transitions of high oscillatory strength, wavelength are given in Table 3. The first singlet state (S1) is found to be at 366 nm in DCM (Fig.5)and 378nm in the gas phase (Fig.5).The second singlet excited state (S2) is present at 326 nm (DCM) and 314 nm (gas phase).The third  singlet excited state (S3) is present at 322 nm (DCM) and 311 nm (gas phase).The Simulated spectrum (Gas and DCM) is illustrated in Fig.5The assigned bands were characterized by (n→π*) and (π→π*) transitions.

Table 3: Absorption energies (λ in nm), oscillator strength (ƒ), and transitions of title compound computed at TD-DFT B3LYP/6-311++G (d, p) level of theory

State

DCM

Gas Phase

Config

f

λ, nm

Excitation energy (eV)

Config

f

λ, nm

Excitation energy(eV)

I

72 -> 76

73 -> 76

75 -> 76

0.0234

366

 

3.3863

72 -> 76

74 -> 76

75 -> 76

0.0066

378

3.2723

II

72 -> 76

0.6083

326

3.7921

74 -> 76

0.5315

314

3.9478

 

73 -> 76

 

 

 

75 -> 76

 

 

 

 

74 -> 76

 

 

 

–

 

 

 

 

75 -> 76

 

 

 

–

 

 

 

III

74 -> 76

0.0703

322

3.8491

72 -> 76

0.0560

311

3.9791

 

75 -> 76

 

 

 

73 -> 76

 

 

 

 

75 -> 78

 

 

 

74 -> 76

 

 

 

 

–

 

 

 

75 -> 76

 

 

 

 

–

 

 

75 -> 78

 

 

 

IV

71 -> 76

0.0523

294     4.2073

71 -> 76

0.0272

291

4.2563

 

72 -> 76

 

 

72 -> 76

 

 

 

 

73 -> 76

 

 

73 -> 76

 

 

 

 

75 -> 76

 

 

74 -> 76

 

 

 

 

–

 

 

75 -> 76

 

 

 

V

71 -> 76

0.0373

286          4.3229

71 -> 76

0.0165

281

4.4066

 

72 -> 76

 

 

72 -> 76

 

 

 

 

73 -> 76

 

 

74 -> 79

 

 

 

 

73 -> 79

 

 

–

 

 

 
 
Figure 5: The Simulated UV-visible absorption spectra for the title compound in vacuum and DCM solventcomputed at B3LYP/6-311++G (d, p) level of theory.
 
Figure 5: The Simulated UV-visible absorption spectra for the title compound in vacuum and DCM solventcomputed at B3LYP/6-311++G (d, p) level of theory.
Click on image to enlarge
 
 
Global Chemical Reactivity Descriptors

The highest molecular orbital and lowest molecular orbital are called frontier molecular orbitals. The HOMO-LUMO energy value and energy gap values for title compound were computed by the TD-DFT method at B3LYP/6-311G (d, p) basis set in gas phase.HOMO-LUMO plot of title compound is shown in Fig.6the computed gas phase HOMO and LUMO energies are -7.2328 eV and -2.7225 eV respectively.Whereas the energy gap of title compound is4.5103eV. From the HOMO-LUMO energies various chemical reactivity parameters have been derived. The Ionization potential (I), Electron Affinity (A), Chemical hardness (ɳ), Chemical softness (S), Electronic chemical potential (μ), Global Electrophilicity index (ω) parameters were calculatedbased on Koopman’s theorem [26]equation 1-4 [27-30]. The HOMO-LUMO energies and global reactivity parameters are listed in table 5.The global hardness (η ) of 2.2551eV, Chemical Softness (S ) 0.4434eV, chemical potential ( μ) -4.9777 eV, electrophilicity Index ( ω) 4.8554eV suggest the good stability of the compound.

ɳ = ½ (I – A)……                                                                                             (1)

S = 1/η…..                                                                                                         (2)

μ = -½ (I+A)…                                                                                                (3)

ω = μ2 / 2η …..                                                                                                (4)

Figure 6: Frontier molecular orbitals of title Molecule

Figure 6: Frontier molecular orbitals of title Molecule
Click on image to enlarge

Table 4: Global chemical reactivity indices calculated at B3LYP/6-311G++(d,p) level

Parameters

B3LYP/6-311++G(d,p)

ELUMO(eV)

-2.7225eV

EHOMO(eV)

-7.2328eV

D E= ELUMO-EHOMO(eV)

4.5103eV

Electron affinity(A)

2.7225eV

Ionization Energy(I)

7.2328eV

Global Hardness (η)

2.2551eV

Chemical Softness (S)

0.4434eV

Electronic chemical potential (μ)

-4.9777eV

Global electrophilicity Index (ω)

4.8554eV

 Mulliken Atomic Charges

The Mulliken atomic charges play an important role to know the chemical reactivity of compounds. The Mulliken atomic charges calculated and reported of title compound is shown in Table 5.As indicated in table 5The C4 atom carries the larges positive charge 1.657 among other carbon atoms and therefore expected to be the site for nucleophilic attack in title compound, whereas C8 and C10 carries higher negative charge -1.225 and -1.633 respectively in all carbon atoms. The Molecular electrostatic potential plot is shown in Fig.8,this gives information about the chemical reactivity of sites. The dipole moment of the title compound is 3.9 Debye indicates polar nature.

Figure 7: Mulliken atomic charges representation

Figure 7: Mulliken atomic charges representation
Click on image to enlarge

 Table 5: Mulliken atomic charges of Title compound at B3LYP/6-311++G (d, p) level

       Atom

Charge

Atom

Charge

1Cl

0.635

15 H

0.208

2 Cl

0.543

16 C

-0.008

3 O

-0.223

17 H

0.204

4 C

1.657

18 C

-0.667

5 C

0.333

19 H

0.170

6 C

-0.317

20 C

-0.222

7 H

-0.058

21 C

-0.151

8 C

-1.225

22 H

0.211

9 H

0.240

23 C

-0.172

10 C

-1.633

24 C

0.001

11 H

0.101

25 H

0.212

12 C

0.324

26 C

-0.144

13 C

-0.618

27 H

0.214

14 C

0.548

28 F

-0.164

Figure 8: Molecular Electrostatic potential plot of the title compound

Figure 8: Molecular Electrostatic potential plot of the title compound
Click on image to enlarge

 Antimicrobial Activity 0f the Title Compound

The newly synthesized (2E)-3-(2,6-dichlorophenyl)-1-(4-4-Fluoro)-prop-2-en-1-one were screened for their antimicrobial activities in vitro against staphylococcus aureus, bacillus subtillis,Escheria coli salmonella Typhi pathogenic bacteria and three fungi Aspergillus Niger, Aspergillus flavus candida albicans. Antimicrobial activity of title compound was tested using the agar diffusion method [32].The antimicrobial activity data of synthesized compounds, from the result the title compound shows moderate activity against all organisms.

Table 6: Antimicrobial Activity

Product

Bacteria                                                                               Fungi

 

Ec

Bs

St

Sa

An

Af

Ca

Compound

11(25)

12(25)

10(25)

09(25)

08(25)

12(25)

09(25)

Penicillin

15(25)

17(25)

13(25)

13(25)

NA

NA

NA

Nystatin

NA

NA

NA

NA

16(25)

14(25)

13(25)

Zone of inhibition is expressed in mm, Ec-Escherichia coli, An-Aspergillus niger, Sa-Staphylococcus aureus, Af-Aspergillus flavus, Bs- Bacillus subtillis-Salmonella Typhi, Ca- Candida albicans, — No activity, NA-Not Applicable

Conclusion

(2E)-3-(2, 6-dichlorophenyl)-1-(4-4-Fluoro)-prop-2-en-1-one synthesized by claisen-Schimdt condensation and spectroscopic characterization by using FT-IR and 1H NMR and study of molecular structure, bondlength, bond angle etc.by using Density Functional Theory B3LYP/6-311++G(d,p) basis set.It was found that experimental vibrational frequencies show good agreement with the calculated vibrational frequencies. The dipole moment of title compound is 3.9036 Debye shows polar nature. Allhydrogen’s are electropositive except H7 and C10 carries a higher negative charge. In addition to this energy of HOMO-LUMO, thermodynamic properties like Enthalpy, Entropy, and Polarizability are calculated. From the DFTstudy gives information about the reactivity of molecule.The title compound shows moderate activity against all bacteria and fungi.

Acknowledgements

The Authors acknowledge the central instrumentation facility, Savitribai Phule Pune University, Pune for NMR, KTHMCollege, and Nashik for FT-IR spectral analysis. The authors also would like to thank Principal of MGV’S L.V.H.  Arts, Science and Commerce College, Panchvati, Nashik for permission and providing necessary research facilities. Authors are also grateful to Ex Professor A. B. Sawant for Gaussian study.Dr.Apoorva Prashant Hiray, Coordinator,    MG Vidyamandir Institute, is gratefully acknowledged for Gaussian package.

Funding

 No funding was received to carry out the research work presented in this research paper.

Conflict of interest

The author declares that they have no conflict of interest.

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