Molecular Structure Investigation, Spectroscopic Characterization, UV Spectral Analysis and Optical Band Gap Determination of (2E)-3-(3-Bromo- 4methoxyphenyl)-1-(pyridin-2-yl) prop-2-en-1-one A Food Preservative Chalcone
DOI:
https://doi.org/10.26713/jamcnp.v5i2.979Abstract
FT-IR and FT-Raman spectra of food preservative molecule (2E)-3-(3-Bromo-4methoxyphenyl)-1-(pyridin-2-yl) prop-2-en-1-one (PYR) were recorded and analyzed. The equilibrium geometry, various bonding and harmonic vibrational wave numbers have been calculated with the help of density functional theory (DFT) method. The assignments of the vibrational spectra have been carried out with the help of Normal coordinate analysis (NCA) following the scaled quantum chemical force field (SQMF) methodology. The natural bond orbital (NBO) analysis was carried out to reveal the nature of different interactions responsible for the electron delocalization and the charge transfer between the orbital's (\(n\)-\(\pi^*\), \(n\)-\(\sigma^*\), \(\pi\)-\(\pi^*\)). Blue shifting of (36 cm\({}^{-1}\)) C-H stretching mode provides the spectral evidence for the intermolecular interactions of C-H...Br. The optical transmittance provides a way to find the band gap which is determined using Taue plot.
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O. Alver, C. Parlak and M. ¸ Senyel, FT-IR and NMR investigation of 1-phenylpiperazine: A combined experimental and theoretical study, Spectrochim. Acta Part A: Molecular and Biomolecular Spectroscopy 67 (2007), 793.
G.G. Danagulyan, L.G. Sahakyan and G.A. Panosyan, Synthesis of fused systems containing an angular nitrogen atom from substituted 2-benzyl-4-hydrazinopyridimines, Chem. Heterocycl. Compd. 36 (2000), 185.
A.S. El-Shahawy, S.M. Ahmed and N.K. Sayed, INDO/SCF-CI calculations and structural spectroscopic studies of some complexes of 4-hydroxyacetanilide, Spectrochi. Acta Part A: Molecular and Biomolecular Spectroscopy 66 (2007), 143.
M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski and D.J. Fox, Gaussian 09, revision B.01, Gaussian, Inc., Wallingford CT (2010).
E.D. Glendening, A.E. Reed, J.E. Carpenter and F. Weinhold, Nbo Version 3.1, Tci. University of Wisconsin, Madison (1998).
D. Guo and L. Goodman, Nature of barrier forces in acetaldehyde. J. Phys. Chem. 100, 12540 (1996).
A. Gyomore, Z. Kovacs, T. Nagy, V. Kudar, A. Szabo and A. Csampai, DNMR, DFT and preparative study on the conformation of (Z)-4, 5, 6, 7 tetrahydropyrazolo [1, 5-e] benzo [g] [1, 5] diazonin-8-ones and (Z)-4, 5 dihydropyrazolo [1, 5-d] benzo[f] [1, 4] diazocin-7 (6H)-ones, Tetrahedron 64 (2008), 10837.
S. Hilton, S. Naud, J.J. Caldwell, K. Boxall, S. Burns, V.E. Anderson, L. Antoni, C.E. Allen, L.H. Pearl, A.W. Oliver and G. W. Aherne, Identification and characterisation of 2-aminopyridine inhibitors of checkpoint kinase 2, Bioorg. Med. Chem. 18 (2010), 707.
M.H. Huang, Y. Wu, H. Feick, N. Tran, E. Weber and P. Yang, Catalytic growth of zinc oxide nanowires by vapor transport, Adv. Mater. 13 (2001), 113.
P. Jerry Jasinski, J. Ray Butcher, S. Samshuddin, B. Narayana and H.S. Yathiraja, (2E)-3 (3-Bromo-4-methoxyphenyl)-1-(pyridin-2-yl) prop-2-en-one, Acta. Cryst Sec. E 67 (2011), 352.
H. Ji, S.L. Delker, H. Li, P. Martásek, L.J. Roman, T.L. Poulos and R.B. Silverman, Exploration of the active site of neuronal nitric oxide synthase by the design and synthesis of pyrrolidinomethyl 2-aminopyridine derivatives, J. Med. Chem. 19 (2010), 7804.
R.A. Jones and A.G. Moritz, Pyrrole studies–VI. The N- H stretching frequencies of substituted pyrroles: methyl and carbethoxy substituents, Spectrochim. Acta. 21 (1965), 295.
W. Kohn and L.J. Sham, Self-consistent equations including exchange and correlation effects, Physical Review 140 (1965), 1133.
M.M. Krayushkin, I.P. Sedishev, V.N. Yarovenko, I.V. Zavarzin, S.K. Kotovskaya, D.N. Kozhevnikov and V.N. Charushin, Synthesis of pyridines from 1, 2, 4-triazines under high pressure, Russ. J. Org. Chem. 44 (2008), 407.
R. Kurtaran, S. Odabasıoglu, A. Azizoglu, H. Kara and O. Atakol, Experimental and computational study on [2, 6-bis (3, 5-dimethyl-N-pyrazolyl) pyridine]-(dithiocyanato) mercury (II), Polyhedron 26 (2007), 5069.
R.G. Parr and W. Yang, Density-Functional Theory of Atoms and Molecules, International Series of Monographs on Chemistry (1989).
P. Pulay, G. Fogarasi, G. Pongor, J.E. Boggs and A. Vargha, Combination of theoretical ab initio and experimental information to obtain reliable harmonic force constants. Scaled quantum mechanical (QM) force fields for glyoxal, acrolein, butadiene, formaldehyde, and ethylene, J. Am. Chem. Soc. 105 (1983), 7037.
A.E. Reed, L.A. Curtiss and F. Weinhold, Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint, Chem. Rev. 88 (1988), 899.
S. Scheibye, A.A. El-Barbary, S.O. Lawesson, H. Fritz and G. Rihs, Studies on organophosphorus compounds–XLI: Formation of 3-pyrazoline-5-thione disulfides from 3, 5-pyrazolidinediones. Calkylation of 3, 5-pyrazolidinediones, Tetrahedron 38 (1982), 3753.
T. Sundius, Molvib-A flexible program for force field calculations, J. Mol. Struct. 218 (1990), 321.
T. Sundius, Scaling of ab initio force fields by MOLVIB, Vib Spectrosc. 29 (2002), 89.
J. Tauc, Optical properties of amorphous semiconductors, in Amorphous and Liquid Semiconductors, Springer, Boston, MA (1974).
G. Varsanyi, Vibrational Spectra of Benzene Derivatives, Elsevier (2012).
X.D. Yang and Y.Y. Yu, Synthesis, crystal structure and fungicidal activity of 1-(4-chlorophenyl)-2-(5-((3, 5-dimethyl-1H-pyrazol-1-yl) methyl)-4-phenyl-4H-1, 2, 4-triazol-3-ylthio) ethanone, Struct. Chem. 19 (2008), 693.
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