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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

Rahul Ashok Shinde1,2, Vishnu Ashok Adole2*, Bapu Sonu Jagdale1,2 and Thansing Bhavsing Pawar1

1Department of Chemistry, Mahatma Gandhi Vidyamandir’s Loknete Vyankatrao Hiray Arts, Science and Commerce College Panchavati (Affiliated to SP Pune University, Pune), Nashik-422 003, India

2Department of Chemistry, Mahatma Gandhi Vidyamandir’s Arts, Science and Commerce College (Affiliated to Savitribai Phule Pune University, Pune), Manmad-423104, India

Corresponding Author Email: vishnuadole86@gmail.com

DOI : http://dx.doi.org/10.13005/msri.17.special-issue1.07

Article Publishing History
Article Received on : 10 May 2020
Article Accepted on : 01 June 2020
Article Published : 03 Jun 2020
Plagiarism Check: Yes
Reviewed by: Raheleh Farahani
Second Review by: Anuj Saini
Final Approval by: Arunabha Roy
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ABSTRACT:

The present research deals with the synthesis, characterization and density functional theory (DFT) study of (E)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (DTMPP). For the computational investigation, DFT method at B3LYP/6-311++G(d,p) basis set has been used.  Herein, structural properties like molecular structure, bond lengths, and bond angles of the DTMPP have been explored. The all-important examination of the electronic properties; HOMO and LUMO energies were studied by the time-dependent DFT (TD-DFT) method. The experimental and theoretical spectroscopic Investigation on FT-IR, 1HNMR, 13C NMR has been unveiled in the present research. To study the chemical behaviour of the DTMPP, Mulliken atomic charges, molecular electrostatic surface potential, and reactivity descriptors have been explored. The dipole moment of the DTMPP is 1.27 Debye with C1 point group symmetry and -1225.77 a.u. E(B3LYP) energy. The most electropositive carbon and hydrogen atoms in the DTMPP are C14 and H27 respectively. The C1-C6 bond is the longest (1.4089 Å) C=C bond in the DTMPP. The oxygen atom O33 is having short contact interaction with the hydrogen atom H44 with a distance of 3.3258 Å. The molecular electrostatic potential plot predicts the positive electrostatic potential is around hydrogen atoms. The FT-IR assignments were made by comparing the experimental FT-IR absorption peaks with the scaled frequencies obtained using DFT method. Furthermore, some valuable insights on thermochemical data are obtained using the harmonic frequencies at same basis set.

Graphical Abstract

Graphical Abstract
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KEYWORDS: (E)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one; DFT; B3LYP/6-311++G(d,p); Molecular structure; Molecular Electrostatic Surface Potential

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Shinde R. A, Adole V. A, Jagdale B. S, Pawar T. B. 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. Mat. Sci. Res. India; Special Issue (2020).


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Shinde R. A, Adole V. A, Jagdale B. S, Pawar T. B. 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. Mat. Sci. Res. India; Special Issue (2020). Available from: https://bit.ly/2AA8pq1


Introduction

Chalcones are open chain compounds that are considered as pathway to naturally occurring compounds flavonoids and isoflavonoids. Many chalcones and their hybrid derivatives are synthesized in last two decades.1-5 Both natural and synthetic versions of chalcones display enormous applications in pharmacological field.6-10 Structurally, chalcones are 1,3-diaryl-2-propen-1-ones and exist as cis and trans forms; latter being thermodynamically more stable is more predominant. Chalcones are considered as vital intermediates to synthesized wide variety of heterocyclic compounds with broad-spectrum of biological activities.11-16 The extraordinary pharmacological profile of chalcones and their hybrid derivatives include anticancer,17-20 anti-tubercular,21,22  antibacterial,23-26 anti-HIV,27-30 antimalarial,31-34  antioxidants,35-37  antiviral,38-40 antifungal,41-45 cardiovascular,46,47 antitumor,48-50 antiulcer,51 anticonvulsant,52, 53 anti-inflammatory,54-59 activities. Besides, chalcones also exhibit applications in the field of solar cells,60 photo-alignment layer of liquid crystal display,61 optoelectronics,62 corrosion and photo crosslinking,63 and nonlinear optical materials.64-67 All these noteworthy aspects about chalcones make them widely studied and synthesized compounds in the fields of science. Green chemistry has advanced in recent years and many methods have been modified in order increase the reaction efficiency and reduce waste material.68-75 Many methods have been accounted for the synthesis of chalcones; nut still, the most common method which is being used for the synthesis of chalcones is Claisen-Schmidt condensation.5

The field of DFT has attracted researchers due to its wide applications in structural chemistry. Many vital structural parameters could be anticipated with the help of DFT. The molecular properties like molecular structure, bond lengths, and bond angles along with spectroscopic properties like UV-Visible, FT-IR, Raman, and NMR have been largely explored by using DFT method using proper basis set.76-80 To investigate all these important aspects DFT has been employed to study the molecules like 2-arylidene indanone,81 (E)-1-(5-bromo-2-hydroxybenzylidene)semicarbazide,82 (E)-1-(4-bromobenzylidene)semicarbazide,83 3,5-Difluoroaniline,84 (E)-3-[4-(pentyloxy)phenyl]-1-phenylprop-2-en-1-one,85 N-phenylbenzenesulfonamide,86 3-ethynylthiophene,87 SnO2 nanopowder,88 2-Thienylboronic acid,89 3,5-dimethyl-4-methoxybenzoic acid,90 4-hydroxy-3-methoxycinnamaldehyde,91  3– alkyl–4–[3–methoxy–4–(4–methylbenzoxy)benzylidenamino]–4,5–dihydro–1H–1,2,4–triazol–5–ones,92 5-bromo-2-ethoxyphenylboronic acid,93 5-benzyl 2-thiohydantoin,94 Chlorfenson,95 sulfamethoxazole,96 terephthalic acid,97 1-phenyl-2-nitropropene,98 1-bromo-4-nitrobenzene,99 4-bromo-1-(ethoxycarbonyl)piperidine-4-carboxylic acid,100 2-Bromo-1H-Benzimidazol,101 dansyl chloride 102 etc. In view of all these discussed vital aspects of the modern  times, herein I wish report combined experimental and theoretical studies on the molecular structure, FT-IR, NMR, HOMO, LUMO, MESP surface, 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. In the present research, DFT investigation of the optimized molecular structure, bond length, bond angle, Mulliken atomic charges and harmonic vibrational frequencies have been investigated. The important parameters such as total energy, HOMO-LUMO energies, charge distribution, ionization potential, electron affinity, electronegativity, global softness, absolute hardness, global electrophilicity index, chemical potential, charge transfer have been studied using 6-311++G(d,p) basis set.

Materials and Methods

General Remarks

The chemicals (Make- Sigma Aldrich, SD Fine Pvt. Ltd., and Avra synthesis) were purchased from local distributor, Nashik with a high purity. The FT-IR spectrum of the DTMPP was recorded on Shimadzu spectrometer using a KBr disc technique. The NMR experiment was performed on sophisticated multinuclear FT-NMR Spectrometer (500 MHz) model Advance-II (Bruker). The compound was dissolved in chloroform-d. Chemical shifts were reported in ppm relative to tetramethylsilane (TMS). The reaction was followed by using thin-layer chromatography on Merck Aluminium TLC plate, silica gel coated with fluorescent indicator F254. All the glass apparatus were cleaned and dried in oven prior to use.

Experimental procedure for the synthesis of the DTMPP

The DTMPP was synthesized using Claisen-Schmidt condensation reaction. In a typical synthesis method, 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)ethan-1-one (1, 10 mmol) and 3,4,5-trimethoxybenzaldehyde (1, 10 mmol) were mixed and added into mortar and pestle. Equimolar amount of solid NaOH was added. Then the alkaline mixture was grinded until formation of the product. After completion of the reaction (monitored by TLC), the reaction was quenched by pouring onto the crushed ice. It was then acidified by dilute HCl, filtered, dried and recrystallized to give pure crystals of the DTMPP. The reaction is presented in the Scheme 1.

Scheme 1: Synthesis of the DTMPP

Scheme 1
Click on image to enlarge

Computational Details

For DFT calculations Gaussian 03(W) program package is used. All the calculations are performed at optimized by using DFT/B3LYP method using 6-311++G(d,p) basis set. Gauss View 4.1 molecular visualization program is used to visualize the optimized structure. The molecular structure is optimized at the same level. The structural parameters like bond length and bond angles, Mulliken atomic charges, molecular electrostatic surface potential, thermochemical data for the DTMPP were determined. The absorption wavelength (λ in nm), oscillator strength (ƒ), and transitions of DTMPP were computed at TD-B3LYP/6-311++G(d,p) level of theory for B3LYP/6-311G++(d,p) optimized geometry. All the DFT calculations were performed for the optimized molecular structure in the gas phase.

Results and Discussion

Spectral analysis of the DTMPP

The DTMPP was characterized by spectral methods like FTIR, 1H NMR, and 13C NMR. The structure with ring labelling is depicted in Figure 1. The FT-IR spectrum is depicted in Figure 2, 1H NMR in Figure 3, and 13C NMR in Figure 4. In 1H NMR spectrum, the DTMPP has displayed all expected signal. The two protons situated at the C=C (alkene framework) are mutually coupled to each other by a coupling constant, J = 15.6 Hz which suggests the stereochemistry of an olefinic double bond is trans. All other signals in 1H NMR spectrum are ideally matching with structural arrangement of the DTMPP. In 13C NMR spectrum, the very important carbon signal is at 188.49 δ which is ascribed to ketonic carbonyl carbon. Other carbon signals are also correctly matching. The FT-IR spectral assignments were discussed in latter section.

Figure 1: Structure of DTMPP (with ring labeling)

Figure 1
Click on image to enlarge

(E)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

FT-IR (cm-1, KBr) 3055.24, 2931.80, 2846.93, 2337.72, 1651.07, 1597.06, 1496.76, 1442.75, 1327.03, 1180.44, 1026.13, 979.84, 825.53, 771.53, 686.66, 555.50, 516.92; 1H NMR (500 MHz, CDCl3) δ 3.90 (s, 3H), 3.93 (s, 6H), 4.37 – 4.30 (m, 4H), 6.86 (s, 2H), 6.99 – 6.94 (m, 1H), ), 7.38 (d, J = 15.6 Hz, 1H), 7.60 (m, 2H), 7.71 (d, J = 15.6 Hz, 1H); 13C NMR (126 MHz, CDCl3) δ 56.23, 61.04, 64.20, 64.73, 105.53, 117.36, 118.05, 121.02, 122.70, 130.55, 131.98, 140.23, 143.40, 144.32, 147.93, 153.47, 188.49.

Figure 2: FT-IR spectrum of DTMPP

Figure 2
Click on image to enlarge

Figure 3: 1H NMR spectrum of DTMPP

Figure 3
Click on image to enlarge

Figure 4: 13C NMR spectrum of DTMPP

Figure 4
Click on image to enlarge

DFT Study

Molecular structure, bond length, bond angle study

The optimized molecular structure of the DTMPP has been presented in the Figure 5. Optimized bond lengths and bond angles of DTMPP at B3LYP/6-311++G(d,p) are presented in Table 1 and Table 2 respectively. The DTMPP possess aromatic C=C bond lengths from 1.39 Å to 1.40 Å. The alkene (C10=C12) bond is 1.3447 Å long and the carbonyl (C14-O15) bond is 1.2249 Å in length. The C1-C6 bond is the longest (1.4089 Å) C=C bond in the DTMPP. The oxygen atom O33 is having short contact interaction with the hydrogen atom H44 with a distance of 3.3258 Å. The dipole moment of the DTMPP is 1.27 Debye with C1 point group symmetry and -1225.77 a.u. E(B3LYP) energy. The bond angles C23-O32-C28, C21-O31-C25, C25-C28-O32, and C28-C25-O31 are 114.3374, 113.7255, 110.1429, and 110.0488° respectively. Other bond length and bond angle data is also in good agreement.

Figure 5: Optimized Molecular Structure of the DTMPP

Figure 5
Click on image to enlarge

Table 1: Optimized bond lengths of DTMPP at B3LYP/6-311++G(d,p)

Bond lengths (Å)

C1-C2

1.403

C12-C14

1.4843

C25-C28

1.5166

C1-C6

1.4089

C14-O15

1.2249

C25-O31

1.428

C1-C9

1.3684

C14-C16

1.4986

C28-H29

1.096

C2-C3

1.3905

C16-C17

1.4034

C28-H30

1.0904

C2-O33

1.3712

C16-C18

1.4002

C28-O32

1.4321

C3-C4

1.3999

C17-C19

1.3882

O33-C35

1.4344

C3-H7

1.0822

C17-H20

1.0813

O33-H44

3.3258

C4-C5

1.4066

C18-C21

1.3848

O34-C39

1.4224

C4-C10

1.4599

C18-H22

1.0824

C35-H36

1.0896

C5-C6

1.3927

C19-C23

1.393

C35-H37

1.0911

C5-H8

1.0815

C19-H24

1.0833

C35-H38

1.0957

C6-C34

1.3626

C21-C23

1.4073

C39-H40

1.0886

O9-C43

1.435

C21-C31

1.3731

C39-H41

1.0954

C10-H11

1.0874

C23-C32

1.3667

C39-H42

1.0951

C10-C12

1.3447

C25-H26

1.0905

C43-H44

1.0944

C12-H13

1.0817

C25-H27

1.0968

C43-H45

1.0921

C43-H44

1.0896        

Table 2: Optimized bond angles of DTMPP at B3LYP/6-311++G(d,p)

Bond angles (°)

C2-C1-C6

119.203

C15-C14-C16

119.9414

C25-C28-O32

110.1429

C2-C1-O9

119.654

C14-C16-C17

124.1855

C29-C28-H30

109.2448

C6-C1-O9

121.1151

C14-C16-C18

117.105

C29-C28-O32

109.4186

C1-C2-C3

120.5619

C17-C16-C18

118.7092

H30-C28-O32

106.2509

C1-C2-O33

120.8758

C16-C17-C19

120.5274

C21-O31-C25

113.7255

C3-C2-O33

118.4956

C16-C17-H20

121.0765

C23-O32-C28

114.3374

C2-C3-C4

120.6212

C19-C17-H20

118.3819

C2-O33-C35

115.9901

C2-C3-H7

117.6039

C16-C18-C21

121.0782

C6-O34-C39

118.3398

C4-C3-H7

121.7635

C16-C18-H22

119.3046

O33-C35-H36

105.9214

C3-C4-C5

118.8277

C21-C18-H22

119.617

O33-C35-H37

111.2063

C3-C4-C10

123.211

C17-C19-C23

120.381

O33-C35-H38

110.4968

C5-C4-C10

117.9597

C17-C19-H24

121.508

H36-C35-H37

109.8833

C4-C5-C6

120.9288

C23-C19-H24

118.1089

H36-C35-H38

109.2885

C4-C5-H8

118.6506

C18-C21-C23

119.7267

H37-C35-H38

109.9568

C6-C5-H8

120.4205

C18-C21-O31

118.7515

O34-C39-H40

105.7252

C1-C6-C5

119.851

C23-C21-O31

121.5209

O34-C39-H41

111.5441

C1-C6-O34

115.4102

C19-C23-C21

119.5634

O34-C39-H42

111.3529

C5-C6-O34

124.7374

C19-C23-O32

118.4071

H40-C39-H41

109.3594

C1-O9-C43

115.3767

C21-C23-O32

122.0292

H40-C39-H42

109.3165

C4-C10-H11

116.1274

H26-C25-H27

109.1376

H41-C39-H42

109.4515

C4-C10-C12

128.0884

H26-C25-C28

111.3025

O9-C43-H44

110.546

C11-C10-C12

115.7842

H26-C25-O31

106.4255

O9-C43-H45

110.8797

C10-C12-H13

120.8568

H27-C25-C28

110.1061

O9-C43-H46

106.0459

C10-C12-C14

119.9991

H27-C25-O31

109.746

H44-C43-H45

110.1828

H13-C12-C14

119.1389

C28-C25-O31

110.0488

H44-C43-H46

109.5231

C12-C14-O15

120.986

C25-C28-H29

110.1292

H45-C43-H46

109.573

C12-C14-C16

119.0706

C25-C28-H30

111.5645

Mulliken atomic charges and MESP analysis

The Mulliken nuclear charges depend on the electron density. The charge conveyance on the molecule has a fundamental job in the field of quantum mechanical calculations for the molecular systems. The Mulliken atomic charges of the DTMPP are determined by DFT/B3LYP method with a 6-311++G(d,p) basis set are given in Table 3 and the pictorial presentation in Figure 6. Mulliken nuclear charges uncover that all the hydrogen atoms have a net positive charge but H40 atom has a more positive charge (0.131720) than other hydrogen atoms and in this way highly acidic. The C14 atom has the highest net positive charge (0.258693) and the C16 is the most electronegative carbon (-0.172547). Molecular electrostatic potential surface (MESP) is the three dimensional portrayal of the charge distributions in the molecules.

Figure 6: Mulliken atomic charges of DTMPP

Figure 6
Click on image to enlarge

The MESP diagram plotted by employing 6-311++G(d,p) basis set and depicted in Figure 7.81 Over the span of recent years, the molecular electrostatic potential has risen as a persuading tool for exploring molecular interactions. In current science, it has been adequately associated with a wide assortment of biological and chemical platforms. The vital aspects such as nucleophilic and electrophilic reactivity sites, solvent interactions, hydrogen-bonding phenomenon, and non-classical interactions could be anticipated by studying MESP plots. MESP fundamentally used to point out the reactive sites of molecules that enable us to foresee how one molecule can interface with others. The red and yellow colours in the MESP plot indicate the region of high electron density and therefore linked with electrophilic reactivity. On the contrary, the blue colours reveal low electron density and thus susceptible to nucleophilic attacks. The green colours are areas of zero potential. The MESP plot of the DTMPP suggest that the electrophilic attacks are feasible at both aromatic rings; However, ring C is more prone for the attack of electrophiles. The positive potential is around hydrogen atoms.

Table 3: Mulliken atomic charges of DTMPP

Atom

Charge

Atom

Charge

1  C

0.128758

24  H

0.101714

2  C

0.137002

25  C

-0.039861

3  C

-0.028609

26  H

0.122036

4  C

-0.070414

27  H

0.125682

5  C

-0.078696

28  C

-0.033079

6  C

0.186623

29  H

0.128327

7  H

0.084342

30  H

0.121675

8  H

0.105487

31  O

-0.347037

9  O

-0.373934

32  O

-0.347018

10  C

-0.022806

33  O

-0.370983

11  H

0.108857

34  O

-0.352687

12  C

-0.183709

35  C

-0.112558

13  H

0.108190

36  H

0.112704

14  C

0.258693

37  H

0.126112

15  O

-0.332374

38  H

0.093758

16  C

-0.172547

39  C

-0.134310

17  C

-0.042463

40  H

0.131720

18  C

-0.030810

41  H

0.115056

19  C

-0.102820

42  H

0.117146

20  H

0.090052

43  C

-0.106943

21  C

0.156429

44  H

0.103928

22  H

0.117097

45  H

0.116446

23  C

0.171490

46  H

0.114333

Figure 7: Molecular electrostatic potential surface of DTMPP

Figure 7
Click on image to enlarge

HOMO, LUMO, reactivity descriptors, and absorption energies

The pictorial representation of the frontier molecular orbitals (FMOs) has depicted in Figure 8. The FMOs, HOMO and LUMO are crucial to evaluate the reactivity ad the stability of the molecules. More importantly HOMO is connected to the electron donating capacity and the LUMO is connected with electron-accepting ability. The smaller HOMO-LUMO band gap suggests more stability. Thus, the HOMO-LUMO energy gap is the most important indicator of the kinetic stability of molecules. The HOMO and LUMO energies are -6.023 and -2.280 eV individually. The reduction in the HOMO-LUMO energy gap prompts an expansion in polarizability, flexibility, and electron transport in a molecule. The HOMO and LUMO energies are extremely essential as they are linked to ionization enthalpy and electron affinity individually.  The HOMO in the DTMPP is principally located at ring B and C. The LUMO is basically situated at the enone part of the unsaturated system. The energy gap in the DTMPP is 3.783 eV which reveals inevitable charge transfer phenomena taking place within the molecule.

Figure 8: HOMO-LUMO pictures of DTMPP

Figure 8
Click on image to enlarge

With the help of Koopmans’s theorem, various reactivity descriptors are calculated. The important parameters such as total energy, HOMO-LUMO energies, charge distribution, electron affinity, ionization potential, global softness, absolute hardness, electronegativity, global electrophilicity index, chemical potential, and charge transfer are evaluated. The ionization potential (I) and the electron affinity (A) values are 6.023 and 2.280 eV respectively. The electronegativity value in electron volt is 4.15 eV. The absolute hardness (ɳ) is 1.89 eV and the global softness (σ) is 0.53 eV-1. These values indicate that the molecule DTMPP is softer in nature. The global electrophilicity index (ω) is 4.55 eV which tells that the DTMPP is a good electrophile. The chemical potential (Pi) value is -4.15 eV in the DTMPP. The maximum charge transfer (ΔNmax) in the DTMPP is 2.19 eV.

The absorption wavelength (λ in nm), oscillator strength (ƒ), and transitions of DTMPP were computed at TD-B3LYP/6-311++ G(d,p) level of theory for B3LYP/6-311G ++(d,p) optimized geometry in gas phase presented in the Table 4. The UV-Visible spectrum was computed for six excited states. The first excited state absorption wavelength is 375.83 nm with excitation energy of 3.2990 eV and oscillator strength (ƒ), 0.0035. With increase in the number of excited state, there is decrease in the absorption wavelength and increase in the excitation energy.

Table 4: Absorption energies (λ in nm), Oscillator strength (ƒ), and transitions of DTMPP computed at TD-B3LYP/6-311G++(d,p) level of theory for B3LYP/6-311G ++(d, p) optimized geometry in gas phase

Sr. No.

Absorption Wavelength (nm)

Excitation energy (eV)

Excited state

Oscillator strength (f)

1

375.83

3.2990

1

0.0035 

2

363.45

3.4113

2

0.6667 

3

340.53

3.6409

3

0.0441 

4

325.29

3.8115

4

0.1847 

5

311.35

3.9821

5

0.0338 

6

265.39

4.6718

6

0.0812 

Vibrational assignments and thermochemical study

The vibrational assignments for the DTMPP were made by comparing experimental IR spectrum with the theoretical IR spectrum. The DFT based IR absorption values are slightly higher, therefore a scaling factor of 0.96 is used.81 A Comparison between selected theoretical and experimental vibrational assignments has been made and presented in Table 5. The DTMPP contains 46 atoms; therefore, it shows 132 fundamental modes of vibrations.Results indicate that there is ideal matching between experimental and theoretical vibrational peaks. The theoretical IR spectrum is given in Figure 9. The DTMPP has experimental carbonyl vibrational stretching frequency at 1651.07 cm-1. The C=C of enone framework has stretching absorption peak at 1597.06 cm-1. The peak at 3055.24 cm-1 is due to stretching of C12-H bond, asymmetric stretching of C17-H-C19-H and C39-H2 bonds. The IR peak at 1442.75 cm-1 corresponds to scissoring vibration of C39-H2 bond. The vibrational peak at 1327.03 cm-1 is due to wagging vibrations of C25-H2 and C28-H2 bonds. The IR value 1180.44 cm-1 is due to in plane bending vibrations of C17-H, C18-H, and C19-H bonds. The out of plane bending vibration of C5-H bond is observed at 825.53 cm-1. The absorption peak 555.50 cm-1 is ascribed to deformation vibrations of ring A, B, and ring C. Other vibrational assignments were also correctly made using theoretical IR spectrum.

Figure 9: Theoretical IR spectrum of DTMPP

Figure 9
Click on image to enlarge

Table 5: Comparison between selected experimental and theoretical vibrational assignments calculated at 6-311++G(d,p) level

Mode

Computed frequencies (cm-1)

IR Intensity (km) mol-1

Observed frequencies (cm-1)

Assignments

127

3059.26

5.01

3055.24

v C12-H

+ ν asym C17-H-C19-H

118

2944.62

31.79

2931.80

ν asym C39-H2

113

2887.07

51.43

2846.93

ν sym C39-H2

112

1648.18

156.75

1651.07

ν C=O

111

1583.68

338.02

1597.06

ν C10=C12

106

1471.56

124.61

1496.76

ν C=C (ring B)

102

1444.08

77.89

1442.75

ν scis C39-H2

90

1337.20

1.59

1327.03

ω C25-H2 + ω C28-H2

85

1259.33

462.73

t C25-H2

83

1238.51

28.43

ρ C17-H-C19-H

78

1176.00

81.98

1180.44

β C17-H + β C18-H  + β C19-H

65

1030.44

113.60

1026.13

ν C25-O31

62

983.50

100.86

979.84

def ring C

51

815.11

24.10

825.53

γ C5-H

49

790.41

31.37

771.53

ω C17-H-C19-H

44

694.67

5.74

686.66

def ring B

38

559.07

65.24

555.50

def ring A + def ring B + def ring C

v– stretching; sym- symmetric; asym- asymmetric; def- deformation; scis- scissoring β- In-plane bending; γ- out of plane bending; ρ- rocking; t- twisting,  -wagging

The thermochemistry data obtained for the DTMPP from the DFT method at B3LYP/6-311++G(d,p) level is presented in Table 6. In the present study, Etotal, Heat capacity at constant volume, total entropy S, zero point vibrational energy and rotational constants have been evaluated from harmonic vibrational frequencies. The total thermal energy is 244.365 kcal mol-1.  The total entropy is 178.630 cal mol-1K-1; out of which translational freedom is

43.504, rotational is 36.445, and the vibrational is 98.681 cal mol-1K1. The zero point vibrational energy is 228.84140 Kcal mol-1. The information uncovered in this could be helpful for the further evaluation of the other thermodynamic properties.

Table 6: Thermochemical information of DTMPP

Parameter

Value

E total (kcal mol-1)

Translational

Rotational

Vibrational

244.365

0.889

0.889

242.587

Heat Capacity at constant volume,

Cv (cal mol-1K-1)

Translational

Rotational

Vibrational

91.704

 

2.981

2.981

85.742

Total entropy S

(cal mol-1K-1)

Translational

Rotational

Vibrational

178.630

 

43.504

36.445

98.681

Zero point Vibrational Energy Ev0 (Kcal mol-1)

228.84140

Rotational constants (GHZ)

0.53604     0.06036     0.05497

Conclusion

In outline, the current research deals with the synthesis, characterization and DFT study of (E)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (DTMPP). For the computational investigation, DFT method at B3LYP/6-311++G(d,p) basis set has been used. 

  1. Structural properties like molecular structure, bond lengths, and bond angles of the DTMPP have been investigated.  The DTMPP has aromatic C=C bond lengths from 1.39 Å to 1.40 Å. The alkene (C10=C12) bond is 1.3447 Å long and the carbonyl (C14-O15) bond is 1.2249 Å in length. The C1-C6 bond is the longest (1.4089 Å) C=C bond in the DTMPP. The oxygen atom O33 is having short contact interaction with the hydrogen atom H44 with a distance of 3.3258 Å.
  2. Mulliken atomic charges uncover that all hydrogen atoms possess net positive charge but H40 atom has a more positive charge (0.131720) than other hydrogen atoms and thusly exceptionally acidic. The C14 atom has the most noteworthy net positive charge (0.258693) and the C16 is the most electronegative carbon (- 0.172547).
  3. The MESP plot of the DTMPP proposes that the electrophilic attacks are feasible at both aromatic rings; However, ring C is more prone to the attack of electrophiles. The positive potential is around hydrogen atoms.
  4. The HOMO in the DTMPP is essentially situated at ring B and C. The LUMO is fundamentally arranged at the enone part of the unsaturated framework. The energy gap in the DTMPP is 3.783 eV which uncovers inescapable charge transfer phenomena occuring within the molecule.
  5. The absorption wavelength, oscillator strength, and transitions of DTMPP were computed at TD-B3LYP/6-311++G(d,p) level of theory for B3LYP/6-311G ++(d,p) basis set. The UV-Visible spectrum was computed for six excited states. The first excited state absorption wavelength is 375.83 nm with excitation energy of 3.2990 eV and oscillator strength (ƒ), 0.0035. With increase in the number of excited state, there is decrease in the absorption wavelength and increase in the excitation energy.
  6. The vibrational assignments for the DTMPP were made by comparing the experimental IR spectrum with the theoretical IR spectrum. The DTMPP contains 46 atoms; along these lines, it shows 132 fundamental modes of vibrations. The vibrational outcome shows that there is a perfect matching between experimental and theoretical vibrational peaks.
  7. Etotal, heat capacity at constant volume, total entropy, zero point vibrational energy and rotational constants have been evaluated from harmonic vibrational frequencies.

Acknowledgments

Authors acknowledge Central instrumentation facility, Savitribai Phule Pune University, Pune for NMR and CIC, KTHM College, Nashik for FT-IR spectral analysis. Authors also would like to thank principal of Arts, Science and Commerce College, Manmad, for permission and providing necessary research facilities. Authors are very grateful to Prof. Arun B. Sawant his generous help in the Gaussian guidance. Dr. Aapoorva Prashant Hiray, Coordinator, MG Vidyamandir Institute, is gratefully acknowledged for Gaussian package.

Funding

We have not received any kind of fund for the research work and this work is self-funded.

Conflict of Interest

Authors declared that he do not have any conflict of interest regarding this research article.

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