THE ELECTRONIC STRUCTURE, STABILITY, THERMODYNAMICS AND VIBRATIONAL STUDY OF CIS ALKENYL SUBSTITUTED CHALCONES BY DENSITY FUNCTIONAL THEORY CALCULATIONS
Keywords:
Stability, cis chalcone, DFT, FMO, MEP and NLO.
Abstract
In this research, structural analysis and stability of six cis chalcone conformers were investigated, compared with trans conformers using the DFT-B3LYP method and basis set 6-311++G(d,p). Results obtained found that 1-Butenyl cis Chalcone (1-BC) possesses the greatest stability. The polarity of the solvent and the geometry of the conformer appeared to have a significant impact on the stability of the conformers. Additionally, cis 1-BC was appeared to cause the greatest shifts (7 cm-1-gas,6 cm-1-n-hexane and 6 cm-1-ethanol) in the magnitudes of vibrational frequencies of cis unsubstituted CA followed by cis divinyl chalcone (DVC) and cis E-propenyl chalcone (E-PC). It is revealed that the 2-butenyl chalcone (2-BC) constitutes the highest values of Thermal-Energy (T-E), Entropy- (S) and Heat -Capacity (Cv).
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References
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Goto, Y., Hayashi, A., Kimura, Y. and Nakayama, M. (1991) Second Harmonic Generation and Crystal Growth of Substituted Thienyl Chalcone. J. Cryst. Growth 108(3-4): 688–698.
Broichhagen, J., Frank, J. A. and Trauner, D. (2015) A Roadmap to Success in Photopharmacology. Acc. Chem. Res. 48 (7): 1947–1960.
Venkata, B., Lokesh, S., Prasad, Y. R. and Shaik, A. B. (2017) Synthesis and Biological Activity of Novel 2,5-Dichloro-3-Acetylthiophene Chalcone Derivatives. Indian J. Pharm. Educ. Res. 51 (4):679–690.
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Escrivani, O.D., Charlton, L.R., Caruso, B.M., Burle-Caldas, A. G., Borsodi, G. P. M., Zingali, B. R., Arruda-, N., Palmeira-Mello, V.M., de Jesus, B. J., Souza, T. M. A., Abrahim-Vieira, B., Freitag-Pohl, S., Pohl, E., Denny, W. P., Rossi-Bergmann, B. and Steel, G.P. (2021) Chalcones Identify CTXNPx as a Potential Antileishmanial Drug Target. PLoS Negl. Trop. Dis. 15 (11): 1–23.
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Lakshminarayanan, B., Kannappan, N.and Subburaju, T. (2020) Synthesis and Biological Evaluation of Novel Chalcones with Methanesulfonyl End as Potent Analgesic and Anti-Inflammatory Agents. Int. J. Pharmaceutical Sci. Res. Biosci. 11 (10): 4974–4981.
Okolo, E. N., Ugwu, D. I., Ezema, B. E., Ndefo, J. C., Eze, F. U., Ezema, C. G., Ezugwu, J. A. and Ujam, O. T. (2021) New Chalcone Derivatives as Potential Antimicrobial and Antioxidant Agent. Sci. Rep. 11(5): 21781.
Kahssay, W. S., Hailu, S. G. and Desta, T. K. (2021) Design, Synthesis, Characterization and in Vivo Antidiabetic Activity Evaluation of Some Chalcone Derivatives. Drug Des Devel Ther. 17(15): 3119–3129.
Reddy, R. M., Aidhen, S. I., Reddy, A. U., Reddy, B. G., Ingle, K. and Mukhopadhyay, S. (2019) Synthesis of 4-C-β-D-Glucosylated Isoliquiritigenin and Analogues for Aldose Reductase Inhibition Studies. Eur. J. Org. Chem.2019(24):3937–3948.
Bui, T. H., Nguyen, N. T., Dang, P. H., Nguyen, H. X., Thanh, M. and Nguyen, T. (2016) Design and Synthesis of Chalcone Derivatives as Potential Non-Purine Xanthine Oxidase Inhibitors. Springer-plus 5 (1): 1789.
Zhuang, C., Zhang, W., Sheng, C., Zhang, W., Xing, C. and Miao, Z. (2017) Chalcone: A Privileged Structure in Medicinal Chemistry. Chem. Rev.117(12):7762–7810.
Xie, Y., Wang, Z., Wang, D., Zhou, Y., Lei, Y., Gao, W., Liu, M., Huang, X. and Wu, H. (2021) Reversible Photochromic Properties of 4,5,6-Triaryl-4: H -Pyran Derivatives in a Solid State. Mater. Chem. Front. 5 (8): 3413–3421.
Hussein, H.A. and Fadhil, G. F. (2020) Theoretical Investigation of Para Amino-Dichloro Chalcone Isomers,Part I : A DFT Structure — Stability Study. J Phys Org Chem. 4: 1–15.
Wachter, N. M., Rani, N., Zolfaghari, A., Tarbox, H. and Mazumder, S. (2020) DFT Investigations of the Unusual Reactivity of 2-Pyridine carboxaldehyde in Base-Catalyzed Aldol Reactions with Acetophenone. J. Phys. Org. Chem. 33 (5): 1–14.
Naresh, P., Pramodh, B., Naveen, S., Ganguly, S., Panda, J., Sunitha, K., Maniukiewicz, W. and Lokanath, N. K. (2021) Cis and Trans Isomers of 1-(5-Bromothiophen-2-Yl)-3-(10-Chloroanthracen-9-Yl) Prop-2-En-1-On e: Synthesis and Characterization. J. Mol. Struct. 1236: 130228.
Hussein, H. A. (2023) A DFT- study of structural-stability, Mulliken charges, MEP, FMO, and NLO properties of trans alkenyl- substituted- chalcones conformers, theoretical study. Structural Chemistry.
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A.J.E., Jr, Peralta, F., Ogliaro, M.B.J.J., Heyd, E., Brothers, K., Kudin, N., Staroverov, V., Keith, N.T., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewsk, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, Ö., Foresman, J.B., Ortiz, J.V., Cioslowski, J. and Fox, D.J. (2009) Gaussian 09, Revision D.01. Gaussian, Inc., Wallingford CT.
Dennington, R., Keith, T. and Millam, J. (2009) Gauss View, Version 5. Semichem Inc., Shawnee Mission.
Stephens, P.J., Devlin, F.J., Chabalowski, C.F. and Frisch, M.J. (1994) Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J Phys Chem 98(45):11623–11627.
Becke, D.A. (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648–5652.
Lee, C., Yang, W. andParr, R.G. (1988) Development of the colic-salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785–789.
Tomasi, J., Mennucci, B. and Cancès, E. (1999) The IEF Version of the PCM Solvation Method: An Overview of a New Method Addressed to Study Molecular Solutes at the QM Ab Initio Level. J. Mol. Struct. THEOCHEM 464(1–3): 211–226.
Tomasi, J., Mennucci, B. and Cammi, R. (2005) Quantum Mechanical Continuum Solvation Models. Chem. Rev. 105 (8): 2999–3093.
Mohbiya, D. R. and Sekar, N. (2018) Tuning ‘Stokes Shift’ and ICT Character by Varying the Donor Group in Imidazo[1,5 a]Pyridines: A Combined Optical, DFT, TD-DFT and NLO Approach. Chemistry Select 3(6): 1635–1644.
Balci, K. and Akyuz, S. (2008) A vibrational spectroscopic investigation on benzocaine molecule. Vib Spectrosc 48(2):215–228.
Sundaraganesan N, Ilakiamani S, Saleem H, Wojciechowski PM, Michalska D (2005) FT-raman and FT-IR spectra, vibrational assignments and density functional studies of 5-bromo-2-nitropyridine. Spectrochim Acta - Part A Mol Biomol Spectrosc 61(13– 14):2995–3001. https://doi.org/10.1016/j.saa.2004.11.016
Valverde, C., Ribeiro, Í.N., Soares, J.V.B., Baseia, B. and Osório, F.A.P. (2019) Prediction of the linear and nonlinear optical properties of a schiff base derivatives via DFT. Adv Condens Matter Phys.
Sobhi, C., Nacereddine K.A., Djerourou, A., Ríos- Gutiérrez, M. and Domingo, L.R. (2017) A DFT study of the mechanism and selectivities of the [3 + 2] cycloaddition reaction between 3- (benzylidene eamino) oxindole and trans-β-nitrostyrene. J Phys Org Chem 30(6):1–9.
Miar, M., Shiroudi, A., Pourshamsian, K., Oliaey, A.R. and Hatamjafari, F. (2021) Theoretical investigations on the HOMO–LUMO gap and global reactivity descriptor studies, natural bond orbital, and nucleus-independent chemical shifts analyses of 3-pheny lben zo[d]thiazo le-2(3h)-imine and its para-substituted derivatives: solvent and subs. J Chem Res 45(1–2):147–158.
Kumar, A., Deval, V., Tandon, P., Gupta, A. and D’Silva, E.D. (2014) Experimental and theoretical (FT-IR, FT-Raman, UV-Vis, NMR) spectroscopic analysis and first order hyperpolarizability studies of non-linear optical material: (2E)-3-[4-(methylsulfanyl) phenyl]- 1-(4-nitrophenyl) prop-2-en-1-one using density functional theory. Spectrochim Acta - Part A Mol Biomol Spectrosc 130:41–53.
Michelini, L. J., Castro, M. R. C., Custodio, J. M. F., Naves, L. F. N., Vaz, W. F., Lobón, G. S., Martins, F. T., Perez, C. N. and Napolitano, H. B. (2018) A Novel Potential Anticancer Chalcone: Synthesis, Crystal Structure and Cytotoxic Assay. J. Mol. Struct. 1168, 309–315.
Panicker, C. Y., Varghese, H. T., Nayak, P. S., Narayana, B., Sarojini, B. K., Fun, H. K., War, J. A., Srivastava, S. K. and Alsenoy, C. V. (2015) Infrared Spectrum, NBO, HOMO-LUMO, MEP and Molecular Docking Studies (2E)-3-(3-Nitrophenyl)-1-[4-Piperidin-1-Yl] Prop-2-En-1-One.Spectrochim. Acta - Part A Mol. Biomol. Spectrosc. 148: 18–28.
Wang, H., Wang, L., Shen, S., Zhang, W., Li, M., Du, L., Zheng, X., Lee, D., Wang, H. and Wang, L. (2014) Effects of hydrogen bond and solvent polarity on the C = O stretching of bis (2- thienyl) ketone in solution effects of hydrogen bond and solvent polarity on the C = O stretching of bis (2-thienyl) ketone in solution. 9(2012):12450.
Kolling, W. O. (1999) Effect of Hydrogen Bonding Solvents on the Infrared Absorption Band for the Fundamental Vibration of the Carbonyl Group in 1,1,3,3-Tetramethylurea. Transactions of the Kansas Academy of Science. 102 (1):53-56.
Zaini, M. F., Arshad, S., Thanigaimani, K., Khalib, N. C., Zainuri, D.A., Abdullah, M. and Razak, I. A. (2019) New Halogenated Chalcones: Synthesis, Crystal Structure, Spectroscopic and Theoretical Analyses for Third-Order Nonlinear Optical Properties. J. Mol. Struct. 1195 (4): 606–619.
Kostanecki, S. and Tambor, J. (1899) Ueber Die Sechs Isomeren Monooxybenzalace tophenone (Monooxychalkone). Eur. J. Inorg. Chem. 32(2): 1921–1926.
Abbas, A., Gökce, H., Bahc¸eli, S. and Naseer, M. M. (2014), Spectroscopic (FT-IR, Raman, NMR and UV-Vis.) and Quantum Chemical Investigations of (E)-3-[4-(Pentyloxy)Phenyl]-1-Phenylprop-2-En-1-One. J. Mol. Struct. 1075 (5): 352–364.
Zaini, M. F., Razak, I. A. and Anis, M. Z. (2019) Crystal Structure, Hirshfeld Surface Analysis and DFT Studies of (E) -1- (4-Bromophenyl) -3- (3-Fluoro- Phenyl) Prop-2-En-1-One. Res. Commun. 75(1): 58–63.
Goto, Y., Hayashi, A., Kimura, Y. and Nakayama, M. (1991) Second Harmonic Generation and Crystal Growth of Substituted Thienyl Chalcone. J. Cryst. Growth 108(3-4): 688–698.
Broichhagen, J., Frank, J. A. and Trauner, D. (2015) A Roadmap to Success in Photopharmacology. Acc. Chem. Res. 48 (7): 1947–1960.
Venkata, B., Lokesh, S., Prasad, Y. R. and Shaik, A. B. (2017) Synthesis and Biological Activity of Novel 2,5-Dichloro-3-Acetylthiophene Chalcone Derivatives. Indian J. Pharm. Educ. Res. 51 (4):679–690.
Ibrahim, T. S., Moustafa, A. H., Almalki, A. J., Allam, R. M., Althagafi, A., Shadab, M. and Mohamed, M. F. A. (2021) Novel Chalcone / Aryl Carboximidamide Hybrids as Potent Anti-Inflammatory via Inhibition of Prostaglandin E2 and Inducible NO Synthase Activities: Design, Synthesis, Molecular Docking Studies and ADMET Prediction. J. Enzyme Inhib. Med. Chem. 36 (1):1067–1078.
Escrivani, O.D., Charlton, L.R., Caruso, B.M., Burle-Caldas, A. G., Borsodi, G. P. M., Zingali, B. R., Arruda-, N., Palmeira-Mello, V.M., de Jesus, B. J., Souza, T. M. A., Abrahim-Vieira, B., Freitag-Pohl, S., Pohl, E., Denny, W. P., Rossi-Bergmann, B. and Steel, G.P. (2021) Chalcones Identify CTXNPx as a Potential Antileishmanial Drug Target. PLoS Negl. Trop. Dis. 15 (11): 1–23.
Qin, H., Zhang, Z., Lekkala, R., Alsulami, H. and Rakesh, K. P. (2020) hemistry Chalcone Hybrids as Privileged Scaffolds in Antimalarial Drug Discovery: A Key Review. Eur. J. Med. Chem. 193 (1): 112215.
Lakshminarayanan, B., Kannappan, N.and Subburaju, T. (2020) Synthesis and Biological Evaluation of Novel Chalcones with Methanesulfonyl End as Potent Analgesic and Anti-Inflammatory Agents. Int. J. Pharmaceutical Sci. Res. Biosci. 11 (10): 4974–4981.
Okolo, E. N., Ugwu, D. I., Ezema, B. E., Ndefo, J. C., Eze, F. U., Ezema, C. G., Ezugwu, J. A. and Ujam, O. T. (2021) New Chalcone Derivatives as Potential Antimicrobial and Antioxidant Agent. Sci. Rep. 11(5): 21781.
Kahssay, W. S., Hailu, S. G. and Desta, T. K. (2021) Design, Synthesis, Characterization and in Vivo Antidiabetic Activity Evaluation of Some Chalcone Derivatives. Drug Des Devel Ther. 17(15): 3119–3129.
Reddy, R. M., Aidhen, S. I., Reddy, A. U., Reddy, B. G., Ingle, K. and Mukhopadhyay, S. (2019) Synthesis of 4-C-β-D-Glucosylated Isoliquiritigenin and Analogues for Aldose Reductase Inhibition Studies. Eur. J. Org. Chem.2019(24):3937–3948.
Bui, T. H., Nguyen, N. T., Dang, P. H., Nguyen, H. X., Thanh, M. and Nguyen, T. (2016) Design and Synthesis of Chalcone Derivatives as Potential Non-Purine Xanthine Oxidase Inhibitors. Springer-plus 5 (1): 1789.
Zhuang, C., Zhang, W., Sheng, C., Zhang, W., Xing, C. and Miao, Z. (2017) Chalcone: A Privileged Structure in Medicinal Chemistry. Chem. Rev.117(12):7762–7810.
Xie, Y., Wang, Z., Wang, D., Zhou, Y., Lei, Y., Gao, W., Liu, M., Huang, X. and Wu, H. (2021) Reversible Photochromic Properties of 4,5,6-Triaryl-4: H -Pyran Derivatives in a Solid State. Mater. Chem. Front. 5 (8): 3413–3421.
Hussein, H.A. and Fadhil, G. F. (2020) Theoretical Investigation of Para Amino-Dichloro Chalcone Isomers,Part I : A DFT Structure — Stability Study. J Phys Org Chem. 4: 1–15.
Wachter, N. M., Rani, N., Zolfaghari, A., Tarbox, H. and Mazumder, S. (2020) DFT Investigations of the Unusual Reactivity of 2-Pyridine carboxaldehyde in Base-Catalyzed Aldol Reactions with Acetophenone. J. Phys. Org. Chem. 33 (5): 1–14.
Naresh, P., Pramodh, B., Naveen, S., Ganguly, S., Panda, J., Sunitha, K., Maniukiewicz, W. and Lokanath, N. K. (2021) Cis and Trans Isomers of 1-(5-Bromothiophen-2-Yl)-3-(10-Chloroanthracen-9-Yl) Prop-2-En-1-On e: Synthesis and Characterization. J. Mol. Struct. 1236: 130228.
Hussein, H. A. (2023) A DFT- study of structural-stability, Mulliken charges, MEP, FMO, and NLO properties of trans alkenyl- substituted- chalcones conformers, theoretical study. Structural Chemistry.
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A.J.E., Jr, Peralta, F., Ogliaro, M.B.J.J., Heyd, E., Brothers, K., Kudin, N., Staroverov, V., Keith, N.T., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewsk, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, Ö., Foresman, J.B., Ortiz, J.V., Cioslowski, J. and Fox, D.J. (2009) Gaussian 09, Revision D.01. Gaussian, Inc., Wallingford CT.
Dennington, R., Keith, T. and Millam, J. (2009) Gauss View, Version 5. Semichem Inc., Shawnee Mission.
Stephens, P.J., Devlin, F.J., Chabalowski, C.F. and Frisch, M.J. (1994) Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J Phys Chem 98(45):11623–11627.
Becke, D.A. (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648–5652.
Lee, C., Yang, W. andParr, R.G. (1988) Development of the colic-salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785–789.
Tomasi, J., Mennucci, B. and Cancès, E. (1999) The IEF Version of the PCM Solvation Method: An Overview of a New Method Addressed to Study Molecular Solutes at the QM Ab Initio Level. J. Mol. Struct. THEOCHEM 464(1–3): 211–226.
Tomasi, J., Mennucci, B. and Cammi, R. (2005) Quantum Mechanical Continuum Solvation Models. Chem. Rev. 105 (8): 2999–3093.
Mohbiya, D. R. and Sekar, N. (2018) Tuning ‘Stokes Shift’ and ICT Character by Varying the Donor Group in Imidazo[1,5 a]Pyridines: A Combined Optical, DFT, TD-DFT and NLO Approach. Chemistry Select 3(6): 1635–1644.
Balci, K. and Akyuz, S. (2008) A vibrational spectroscopic investigation on benzocaine molecule. Vib Spectrosc 48(2):215–228.
Sundaraganesan N, Ilakiamani S, Saleem H, Wojciechowski PM, Michalska D (2005) FT-raman and FT-IR spectra, vibrational assignments and density functional studies of 5-bromo-2-nitropyridine. Spectrochim Acta - Part A Mol Biomol Spectrosc 61(13– 14):2995–3001. https://doi.org/10.1016/j.saa.2004.11.016
Valverde, C., Ribeiro, Í.N., Soares, J.V.B., Baseia, B. and Osório, F.A.P. (2019) Prediction of the linear and nonlinear optical properties of a schiff base derivatives via DFT. Adv Condens Matter Phys.
Sobhi, C., Nacereddine K.A., Djerourou, A., Ríos- Gutiérrez, M. and Domingo, L.R. (2017) A DFT study of the mechanism and selectivities of the [3 + 2] cycloaddition reaction between 3- (benzylidene eamino) oxindole and trans-β-nitrostyrene. J Phys Org Chem 30(6):1–9.
Miar, M., Shiroudi, A., Pourshamsian, K., Oliaey, A.R. and Hatamjafari, F. (2021) Theoretical investigations on the HOMO–LUMO gap and global reactivity descriptor studies, natural bond orbital, and nucleus-independent chemical shifts analyses of 3-pheny lben zo[d]thiazo le-2(3h)-imine and its para-substituted derivatives: solvent and subs. J Chem Res 45(1–2):147–158.
Kumar, A., Deval, V., Tandon, P., Gupta, A. and D’Silva, E.D. (2014) Experimental and theoretical (FT-IR, FT-Raman, UV-Vis, NMR) spectroscopic analysis and first order hyperpolarizability studies of non-linear optical material: (2E)-3-[4-(methylsulfanyl) phenyl]- 1-(4-nitrophenyl) prop-2-en-1-one using density functional theory. Spectrochim Acta - Part A Mol Biomol Spectrosc 130:41–53.
Michelini, L. J., Castro, M. R. C., Custodio, J. M. F., Naves, L. F. N., Vaz, W. F., Lobón, G. S., Martins, F. T., Perez, C. N. and Napolitano, H. B. (2018) A Novel Potential Anticancer Chalcone: Synthesis, Crystal Structure and Cytotoxic Assay. J. Mol. Struct. 1168, 309–315.
Panicker, C. Y., Varghese, H. T., Nayak, P. S., Narayana, B., Sarojini, B. K., Fun, H. K., War, J. A., Srivastava, S. K. and Alsenoy, C. V. (2015) Infrared Spectrum, NBO, HOMO-LUMO, MEP and Molecular Docking Studies (2E)-3-(3-Nitrophenyl)-1-[4-Piperidin-1-Yl] Prop-2-En-1-One.Spectrochim. Acta - Part A Mol. Biomol. Spectrosc. 148: 18–28.
Wang, H., Wang, L., Shen, S., Zhang, W., Li, M., Du, L., Zheng, X., Lee, D., Wang, H. and Wang, L. (2014) Effects of hydrogen bond and solvent polarity on the C = O stretching of bis (2- thienyl) ketone in solution effects of hydrogen bond and solvent polarity on the C = O stretching of bis (2-thienyl) ketone in solution. 9(2012):12450.
Kolling, W. O. (1999) Effect of Hydrogen Bonding Solvents on the Infrared Absorption Band for the Fundamental Vibration of the Carbonyl Group in 1,1,3,3-Tetramethylurea. Transactions of the Kansas Academy of Science. 102 (1):53-56.
Published
2023-12-24
How to Cite
HUSSEIN, H. A. (2023). THE ELECTRONIC STRUCTURE, STABILITY, THERMODYNAMICS AND VIBRATIONAL STUDY OF CIS ALKENYL SUBSTITUTED CHALCONES BY DENSITY FUNCTIONAL THEORY CALCULATIONS. Journal of Duhok University, 26(2), 466-479. https://doi.org/10.26682/sjuod.2023.26.2.40
Section
Pure and Engineering Sciences
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