Structure Characterization, Spectroscopic investigation and Nonlinear Optical Study using Density Functional Theory of (E)-1-(4-Chlorophenyl)-3-(4-methylphenyl) prop-2-en-1-one

 

Virupakshi M. Bhumannavar^1,2*, Parutagouda Shankaragouda Patil³, Neelamma B. Gummagol²

¹Department of Physics, Hirasugar Institute of Technology, Nidasoshi - 591236, Karnataka, India.

²K. L. E. Institute of Technology, Opposite Airport, Gokul, Hubballi - 580030, Karnataka, India.

³B.L.D.E.A’S, S. B. Arts and K. C. P. Science College Vijayapur - 586103, Karnataka, India.

*Corresponding Author E-mail: vbhumannavar@gmail.com

The structural confirmation of the (E)-1-(4-Chlorophenyl)-3-(4-methylphenyl)prop-2-en-1-one compound is done by experimental techniques. Experimental techniques FTIR, proton NMR, UV-Visible, performed for the compound. The experimentally obtained results are compared with theoretically (density functional theory) obtained results. The decomposition and melting point of the compound is obtained by TGA and DTA. Density functional theory is performed for the (E)-1-(4-Chlorophenyl)-3-(4-methylphenyl)prop-2-en-1-one compound B3LYP/6-311G++(d,p) basis set. Time dependent density functional theory calculated for three different methods B3LYP, Hartree-Fock and CAMB3LYP also employed for the MLCC at 6-311G++(d,p) basis set. The MLCC compound is having the total dipole moment 4.45 D. The static (ω=0.0) mean polarizability 17.40 x10^-24 esu, anisotropic polarizability 23.37 x10^-24esu, first hyperpolarizability 11.84 x10^-30 esu, second hyperpolarizability 11.88x10^-36 esu. Dynamic mean polarizability (ω=0.0569, ω= 0.04282) 17.84 x 10^-24esu, 17.65x10^-24esu. Dynamic anisotropic polarizability (ω=0.0569, ω= 0.04282) 24.26 x 10^-24esu, 23.86 x10^-24esu. Dynamic first hyperpolarizability (ω=0.0569, ω= 0.04282) 18.60 x 10^-30 esu, 15.06 x10^-30 esu. Dynamic second hyperpolarizability (ω=0.0569, ω= 0.04282) 35.37x10^-36 esu, 20.0x10^-36 esu.

 

 

INTRODUCTION:

Chalcones major classes have wide range pharmacological activity importance¹. They are found in edible plants abundantly and having many derivatives heterocyclic rings like pyrimidines, isoxazoles, pyrazolines and cynopyridines². Nonlinear optical materials will have applications in lasers optical sensing, data storage etc^3-4. Two side of the aromatic rings of the compound consists of strong inter molecular interaction due to electron donor and electron acceptor  π-conjugate system5^-6.

 

 

Due to resilient intermolecular interactions second and third order nonlinearity is observed^7-12. Also chalcone have medical applications like antimalarial, anti-fungal, anti-cancer, anti-HIV and antioxidants, anti-ulcer, anti-inflammatory, anti-mitotic etc^13-21. The chalcone have microbial activity, antibacterial activity and anti-infective^22-25. In recent DFT study were carrying out on organic, inorganic, chalcones^26-28. The vibrational study of chalcones is done on chalcones^29-39. Experimental study such as FTIR, ¹H NMR and UV–Visible–NIR was applied to determine structure characterization of chalcone^40-45.  In this research work are concentrated on investigation of molecular structure of (E)-1-(4-Chlorophenyl)-3-(4-methylphenyl)prop-2-en-1-one (MLCC) compound using spectroscopic methods (FTIR, ¹H NMR), linear (UV–Visible–NIR). The stability of the molecule is found by thermal study. To the support of experimental results the theoretical calculations are done with B3LYP/6-311++G(d,p) point of theory. Also molecular orbits, global chemical reactivity descriptors (GCRD), absorption spectra, excitation energies are done with the same theory.

 

MATERIALS AND METHODS:

Synthesis:

The compound (E)-1-(4-Chlorophenyl)-3-(4-methylphenyl)prop-2-en-1-one (MLCC) be synthesized with Claisen –Schmidt Condensation method.4-chloroacetophenone is combined with 4-methylbenzaldehyde in 60 ml methanol, 5ml of 30% NaOH solution. The mixture was stirred for 6 hours and recrystallation in acetone medium. The following fig.1 shows scheme of reaction.

 

Fig.1. Synthesis scheme of MLCC

 

Computation Details:

Theoretical computations for title compound are done with GAUSSIAN 09W program. Optimized geometry of MLCC molecule obtained at B3LYP with 6-311++G (d, p) basis set. Also DFT executed to with 6-311++G(d, p) basis set for MLCC molecule at different levels B3LYP, HF and CAMB3LYP. FTIR and NMR are performed with same basis set. Results are visualized in Gauss View 5 software. Obtained results of title compound were compared and discussed. GAMESS software is run for MLCC molecule by writing a command.

 

Characterization:

The MLCC compound was performed with experimental techniques ¹H NMR spectrum is recorded. Infra red spectrum was recorded using potassium bromide (KBr) pellet method in the range 4000-400cm^-1. The ultraviolet, visible and near infrared regions spectrum for the title compound were measured in the range of 200-3000nm in DMF solution. The analysis of thermal behavior, decaying and melting point of MLCC was done by TG/DTA analysis.

 

RESULT AND DISCUSSION:

Structure Characterization:

The optimization of geometry MLCC compound carry out using DFT at B3LYP/6-311+G(d, p) level. Structure of molecule is given away in Fig. 2.

 

Fig. 2. Geometry optimized molecule of MLCC at B3LYP/6-311++G (d, p) level of theory.

 

From Molecule geometry bond angles, bond length and dihedral angles are obtained. The results obtained from theory and experimental XRD data are shown in Table 1. Patil et al.⁴⁶ report the XRD data of MLCC. The bond lengths of CL1-C7 is 1.76 Å (DFT) and 1.74 Å (XRD), O2-C13 is 1.22 Å (DFT) and 1.23 Å (XRD), C14-C16 is 1.35 Å (DFT) and 1.34 Å (XRD), C23-C28 is 1.40 Å (DFT) and 1.40 Å (XRD), C24-C26 is 1.39 Å (DFT) and 1.39 Å (XRD), C7-C8 is 1.39 Å (DFT) and 1.39 Å (XRD). The bond angles of Cl1-C7-C5 is 119.4º (DFT) and 119.2º (XRD), Cl1-C7-C8 is 119.4º (DFT) and 118.8º (XRD), O2-C13-C12 is 119.5º (DFT) and 119.9º (XRD), O2-C13-C14 is 121.7º (DFT) and 121.8º (XRD), C21-C23-C24 is 117.9 º (DFT) and 117.8 º (XRD), C21-C23-C28 is 121.5º (DFT) and 121.7º (XRD). The torsional angles of C12-C3-C5-H6 is -179.4º (DFT) and -178.4º (XRD), Cl1-C7-C8-C10 is -179.9º (DFT) and -179.0º (XRD), C7-C8-C10-H11 is -179.2º (DFT) and -179.1º (XRD), C5-C7-C8-H9 is -179.9º (DFT) and -179.9º (XRD), C19-C21-C23-C28 is 180.0 º (DFT) and 179.2º (XRD). The bond length, bond angles and torsional angles obtained from DFT and XRD results are having good agreement.

 

Table 1. Experimental (XRD data) and theoretically [B3LYP/6-311+G (d, p)]determined bond length (Å), bond angles, and torsion angles (°) of MLCC molecule.

Bond length	DFT	XRD	Bond angle	DFT	XRD	Torsion angle	DFT	XRD
CL1-C7	1.76	1.74	Cl1-C7-C5	119.4	119.2	C12-C3-C5-H6	-179.4	-178.4
O2-C13	1.22	1.23	Cl1-C7-C8	119.4	118.8	Cl1-C7-C8-C10	-179.9	-179.0
C14-C16	1.35	1.34	O2-C13-C12	119.5	119.9	C7-C8-C10-H11	-179.2	-179.1
C23-C28	1.51	1.5	O2-C13-C14	121.7	121.8	C5-C7-C8-H9	-179.9	-179.9
C23-C24	1.4	1.4	C21-C23-C24	117.9	117.8	C19-C21-C23-C28	180.0	179.2
C24-C26	1.39	1.39	C21-C23-C28	121.5	121.7	C21-C23-C24-H25	-179.8	-180.0
C7-C8	1.39	1.39	C24-C23-C28	120.6	120.5	H25-C24-C26-C18	-179.9	-178.9

 

Vibrational Spectroscopy Study:

The MLCC compounfd has 87 normal modes of vibration  and contains 31 atoms. Compound MLCC functional groups are compared with experimentaly recorded FTIR spectra and theorotically obtained B3LYP/6-311++G(d, p) level. MLCC compound bands along with their vibrational assignment are observed in infra red region (4000- 400 cm^-1). The spectra of compound are shown in Fig.3 their band assignments are shown in Table 2. Arromatic C─H stretching vibrational modes is 3100─3000 cm^-1 regions. The strong unique absorption peak of carbonyl group region in between 1750-1620 cm^-1. Strong peak of C ═ O group vibration is observed at 1657.93 cm^-1 (experimental), and 1636 (theoretical) and for the molecule of MLCC. The theoretical and experimental C ═ C stretching found in the vicinity of 1600-1550 cm^-1. The theoretical and experimental C ═ C stretching found be 1598.32 cm^-1, 1540 cm^-1 respectively. The MLCC molecule has modes of vibrations lie in the range of 1550‒600 cm^-1 for experimental spectra and calculated spectra. The stretching vibration of C‒CH₃  of MLCC is obtained at 1365.58 (expt) and 1364 cm-1 (DFT). The stretching vibration of C‒Cl of a molecule is observed at 756.37 and 548.06 cm^-1 (expt), 764 and 524 cm^-1 (DFT). The C-H bending of aromatic ring is found

 

Fig. 3. Calculated and Experimental FTIR vibrational spectra of MLCC

 

Table 2. Experimental and theoretical (DFT) FT-IR vibrational frequency bands assignments (wavenumbers in cm^-1) of MLCC

EXPT	DFT	Assignment
3308.26	3204, 3180, 3156, 3108	νSym (C-H Aromatic)
3085.55	3076	νSym (C-H Aromatic)
3054.69	-	νSym (C-H Aromatic)
3027.69	3028	νSym (C-H Aromatic)
2917.26	-	νsym (C-H Aromatic)
2857.89	-	νAsym (C-H Aromatic)
1921.86	1716	νAsym (C-H Aromatic)
1657.93	1636	νsym (C=O)
1598.32	1540	νSym (C=C)
1564.60	1516	νSym (C=C Aromatic ring)
1510.99	1492	ν (C-C Aromatic Ring)
1485.47	1444, 1428	δ(C-H, CH3 Group)
1412.41	-	ν (C-C)
1400.08	-	ν (C-C)
1365.58	1364	δ(C-H CH3Group)
1332.09	1316, 1236	δ (C-H Aromatic), δ (C-C Aromatic)
1307.50	-	δ (C-H Aromatic)
1286.61	-	ν (C-C)
1222.37	1220	δ (C-H), δ (C-C Aromatic)
1207.23	1196	δ (C-H Aromatic), δ (C-C Aromatic)
1180.61	1140	δ (C-H Aromatic), δ (C-C Aromatic)
1156.40	1100	δ (C-H Aromatic), δ (C-C Aromatic)
1087.01	1044	δ (C-H Aromatic), δ (C-C Aromatic)
1034.01	1028	δ (C-H Aromatic), δ (C-C Aromatic)
1009.15	-	δ(C-H, C-C Ring),
986.16	964, 908	δ(C-H, C-C Ring),
894.44	860	δ (C-H Aromatic)
834.72	820	δ (C-H)
812.28		δ (C-H Aromatic)
756.37	764	νSym (C-Cl)
737.74	716	γ(C-H)
705.82	684	γ (C=O)
662.88	644	γ (C=O γ(Ring) Wa, τ(Ring)
599.55	548	δ (C-H)
548.06	524	δ (C-Cl), γ(C-H)
502.70	508	γ(C-H Ben Ring)
488.92	484	τ (C-C-C Ben Ring)
464.06	-	τ (C-H)

ν-Stretching; δ-In plane bending; γ-Out of plane bending; τ-Torsional. in the range of 840 cm^-1 – 710 cm^-1. The C-C bending of aromatic ring is found in the range of 1600 cm^-1 – 1450 cm^-1. The details of the functional vibrational frequencies are assigned. In presumption, the results of FTIR vibrations calculated and theoretical functional groups frequencies are good agreement with each other. Hence, Vibrational spectroscopic study authenticates Functional groups and their molecular structure of MLCC.

 

¹H NMR Analysis:

The number of protons and molecular structure of  tittle compound MLCC are confirmed.  The combined ¹H NMR spectra of experimental and theoretical are given away in Fig. 4 and their relevant chemical shifts (δ) are given in Table 3.

 

Fig. 4. The theoretical and experimental ¹H NMR spectra for MLCC.

 

MLCC molecular structure has 13 protons. The theoretical ¹H NMR spectra shows that it every proton consists of separate peaks, where as the experimental spectra shows that it consists of compound peaks because of degeneracy. The MLCC molecule will have chemical shifts δ=1 ppm to 8.5 ppm is observed. ¹H NMR spectral study results of experimental and theoretical values are in good correlation with their derivatives.

 

Table 3. The experimental and theoretical (DFT)¹H NMR chemical shifts (δ in ppm) of MLCC.

 

TG/DTA analysis:

The Fig.5 shows Thermo gravimetric (TG) and differential thermal (DT) analysis. A weight of 13.353 mg compound MLCC initially used for investigation. Thermo gravimetric (TG) curve sketch confirms that the weight loss is 1% for a temperature 30-230 ⁰C, due to humidity and unpredictable solvent. The major weight loss is 100% at 312.66⁰C because of decomposition of MLCC. In TGA show that final residual mass is about 0 % heating up to 500⁰C. There is an endothermic peak observed in DTA trace at 160.72 ⁰C which is assigned to melting point of MLCC molecule.

 

Fig. 5. TGA/DTA plots for MLCC crystal

 

Ultra Violet-Visible-Infrared Absorption Spectrum:

Ultra Violet-Visible-Infrared absorption spectrum was obtained for the sample MLCC at the range 200nm-800nm. Two peaks in absorption spectrum corresponding to electronic transitions of π−π* and n−π* and their absorption peaks are 238nm and 316nm respectively. The absorption must be maximum and it will have the peak at 316nm as shown in Fig.6.

 

Fig. 6. The experimental absorption spectra of MLCC

 

From absorption spectrum the energy gap of MLCC was computed from the relation (1) using Tauc's plot⁴⁷.

 

Plotting graph of  verses photon (hν) by taking n=0.5, intersects x-axis and the value of energy gap (E_g) was found to be 3.26 eV (indirect method) and 3.33 eV (direct method) as shown in Fig. 6.

 

TD-DFT Linear Absorption Study:

The electronic excitation, wavelength absorption and oscillator strength can be calculated for three different levels by TD-DFT method with B3LYP/6-311++G(d, p), CAM-B3LYP/6-311++G(d, p) and HF/6-311++G(d, p) basis in gas phase⁴⁸ as shown in Fig.7. The vertical absorption in UV-Vis spectrum corresponds to highest absorption peak. The theoretical absorption vales from TD-DFT Absorption spectrum at for basis set HF, CAM-B3LYP and B3LYP found to be 275.52 nm, 302.62 nm, and be 336.41 nm. The absorption wavelength, excitation energy, oscillation strength and contribution of HOMO-LUMO orbital are revealed in Table 4. Excitation energy of MLCC from TD-CAMB3LYP predicted 4.097 eV.

 

Fig. 7. The calculated absorption spectra of MLCC

 

Table 4. The excitation energy ∆E, oscillator strengths f₀ and major contributions of HOMO-LUMO orbitals of MLCC molecule at different states under TD-DFT using 6-311++G(d, p) basis set.

Method	Electronic transitions	λ Ex	∆E (eV)	f0	Major contributions (in %)
Experimental	-	316	3.9260	-	-
B3LYP	S0→S1	379.51	3.2670	0.0005	H-1→L (51)
	S0→S2	336.41	3.6855	0.8456	H→L (94)
	S0→S3	296.05	4.1880	0.0836	H-2→L (50)
CAM-B3LYP	S0→S1	344.52	3.5988	0.0007	H-3→L (79)
	S0→S2	302.62	4.0970	0.9704	H→L (93)
	S0→S3	258.72	4.7923	0.0025	H-2→L (55)
HF	S0→S1	275.52	4.4999	0.8923	H→L+1 (73)
	S0→S2	265.59	4.6683	0.0293	H-5→L+1 (58)
	S0→S3	230.77	5.3726	0.1551	H-1→L+1 (42)

 

Table 5. The frontier molecular orbital energies (in eV), and global chemical reactivity descriptors (in eV), chemical hardness (η), potential (µ), softness (S), electronegativity (χ), and electrophilic index (ω) of MLCC molecule

 

Frontier Molecular Orbital (FMO):

The frontier molecular orbit (FMO) consists of unoccupied molecular orbital (LUMO) and highest occupied molecular orbital (HOMO). HOMO-LUMO energy gap of compound MLCC theoretically determined by B3LYP/6-311++G (d, p) is 3.70 eV are listed in Table 5. Molecular orbits are shown in Fig. 8. Transition of π→π* orbital strongly suggest that it is system of donor and acceptor. The energy gap of HOMO-LUMO is good agreement calculated is 3.99 eV and excited energy gap 3.926 eV.

 

 

Fig. 8 The HOMO-LUMO plots of MLCC obtained at B3LYP/6-31+G(d, p).

Computational NLO Studies:

From its components with the equations (2), (3), (4), (5) and (6) dipole moment, mean polarizability, anisotropic polarizability, first hyperpolarizability and second hyperpolarizability were calculated^49-50.

 

The compound MLCC dipole moment is listed in Table 6. Static and Polarizability and first hyperpolarizability are calculated from DFT by the basis set B3LYP/6-311++G(d, p) and the dynamic for different frequencies are determined by writing a command in GAMESS software. From GAMESS software dynamic mean polarizability anisotropic polarizability, first hyperpolarizability and second hyperpolarizability are determined.  The results of static (ω=0.0) and dynamic (ω=0.0569, ω= 0.04282) mean polarizability is presented in Table 7. The results of static (ω=0.0) and dynamic (ω=0.0569, ω= 0.04282) anisotropic polarizability are given in Table 7. The results of static (ω=0.0) and dynamic (ω=0.0569, ω= 0.04282) first hyperpolarizability are given in Table 8. The results of static (ω=0.0) and dynamic (ω=0.0569, ω= 0.04282) second hyperpolarizability are given in Table 9.

 

Table 1.The calculated values of static dipole moment (μ) of MLCC in Debye.

 

Table 2.The calculated values of static and dynamic polarizability (α) of MLCC.

Components in (×10−24) esu	ω=0.00	ω=0.0569	ω= 0.04282
αxx	30.85	31.90	31.43
αxy	0.26	0.21	0.23
αyy	17.44	17.68	17.57
αxz	0.81	0.82	0.82
αyz	-0.18	-0.18	-0.18
αzz	3.92	3.94	3.93
αtot	17.40	17.84	17.65
Δα	23.37	24.26	23.86

 

Table 3.The calculated values of static and dynamic first hyperpolarizability (β) of MLCC.

Component in (×10−30) esu	ω=0.00	ω=0.05695	ω= 0.04282
βxxx	2.77	4.72	3.69
βyyy	-0.04	-0.08	-0.06
βzzz	0.01	0.01	0.01
βx	8.40	14.38	11.23
βy	-8.33	-11.78	-10.03
βz	-0.39	-0.54	-0.46
βtotal	11.84	18.60	15.06
β-V	11.84	18.60	15.06

 

Table 4.The calculated values of static and dynamic second hyperpolarizability (γ) of MLCC

Components in (×10−36) esu	ω=0.00	ω=0.05695	ω= 0.04282
γxxxx	48.59	149.38	83.14
γyyyy	0.05	0.15	0.12
γzzzz	0.00	0.00	0.00
γxxyy	5.02	13.00	7.89
γxxzz	0.27	0.52	0.36
γyyzz	0.10	0.13	0.11
‹γ›	11.88	35.37	20.00

 

Global Chemical Reactivity Descriptors (GCRD):

GCRD is one of the important device to identify the chemical stability, hardness, softness, potential, electronegativityand electrophilic index. Calculated GCRD are listed in the table 5. The value hardness must larger so that molecule will be more stable. The relations (7), (8), (9), (10), (11), (12) and (13) are used to calculate parameters. Hardness (η) of MLCC compound is found to be 1.99 eV, softness (S) is 0.25 eV, Potential (µ) is -4.58 eV, Electronegativity (χ) is 4.58 eV, Electrophilic index (ω) is 5.25 eV, Ionization energy (I) is 6.57 eV and Electron affinity (A) is 2.58 eV.

 

CONCLUSION:

The compound MLCC are confirmed with spectroscopic experiments results of FTIR, proton NMR and UV-Visible. The density functional theory is used to obtain optimized geometry by keeping B3LYP/6-311G++(d,p) at the basis set. Theoretical results of bond length, bond angle and torsinal angle are obtained from DFT are compared with XRD results of the crystal. The results are good agreement with each other. Also confirmation of molecular structure is done with proton NMR. Experimental and theoretical (DFT) FTIR spectrum of functional group frequency results are good agreement with each other. The MLCC compound is having the total dipole moment 4.45 D. The static (ω=0.0) mean polarizability 17.40 x10^-24 esu, anisotropic polarizability 23.37 x10^-24 esu, first hyperpolarizability 11.84 x10^-30 esu, second hyperpolarizability 11.88x10^-36 esu. Dynamic mean polarizability (ω=0.0569, ω=0.04282) 17.84 x 10^-24esu, 17.65x10^-24esu. Dynamic anisotropic polarizability (ω=0.0569, ω= 0.04282) 24.26 x 10^-24esu, 23.86 x10^-24esu. Dynamic first hyperpolarizability (ω=0.0569, ω= 0.04282) 18.60 x 10^-30 esu, 15.06 x10^-30 esu. Dynamic second hyperpolarizability (ω=0.0569, ω= 0.04282) 35.37x10^-36 esu, 20.0x10^-36 esu. The values of static and dynamic first hyperpolarizability are close agreement with already reported NLO compounds. This compound will be helpful in the field nonlinear optics applications.

 

CONFLICT OF INTEREST:

The authors have no conflicts of interest regarding this investigation.

 

ACKNOWLEDGMENTS:

I thank Dr. Basavaraj Anami Principal KLE Institute of Technology Hubballi, India for encouraging carrying out the study. I thank Dr. S.C. Kamate, Principal Hirasugar Institute of Technology Nidasoshi for constant support. I thank USIC Karnatak University Dharwad for providing the instrumental study.

 

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Received on 16.11.2021                    Modified on 12.01.2022

Accepted on 28.02.2022                   ©AJRC All right reserved