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2020 | 147 | 88-103
Article title

FT-IR and NMR spectral LFER model analysis on some 3-(1-naphthyl)-1-substituted phenyl chalcones

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In this investigation, the authors predicted the effects of substituents on the functional groups of the titled chalcones using Linear Free Energy Relationship through Hammett equation with its constants and Swain-Lupton parameters. The LFER model statistical analysis was carried out using single and multi-linear regression analysis in MS Office 365 XL package. From the LFER analysis outcome, the influence of substituents on the spectroscopic functionality were discussed with their electronic effects such as, polar, inductive, resonance, field and conjugation. The titled compounds were prepared by solvent-free Aldol-Condensation method. The prepared compounds were characterised by their physical constants, micro analysis and spectroscopic data (FT-IR, NMR and Mass).
Physical description
  • Department of Chemistry, National College, Tiruchirappalli - 620 001, India
  • Department of Chemistry, National College, Tiruchirappalli - 620 001, India
  • Department of Chemistry, Annamalai University, Annamalainagar - 608 002, India
  • Department of Chemistry, Sourashtra College, Madurai - 625 004, India
  • Department of Chemistry, Annamalai University, Annamalainagar - 608 002, India
  • [1] M. Neurock and M. T. Klein, Linear Free Energy Relationships in Kinetic Analyses: Applications of Quantum Chemistry. J. Polycyl. Aromat. Compds. vol. 3, no. 4, 2006, pp. 231-246.
  • [2] E. S. Lewis, Rate‐equilibrium LFER characterization of transition states: The interpretation of α. J. Phys. Org. Chem. vol. 3, no.1, 1990, pp. 1-8.
  • [3] E. Rosta and A. Warshel, On the Origins of the Linear Free Energy Relationships: Exploring the Nature of the Off-Diagonal Coupling Elements in SN2 Reactions, J. Chem. Theory. Comput. Vol. 8, no. 10, 2012, pp. 3574-3585.
  • [4] K. Ranganathan, D. Kamalakkannan, R. Suresh, S. P. Sakthinathan, R. Arulkumaran, R. Sundararajan, V. Manikandan and G. Thirunarayanan, Synthesis, Hammett spectral correlation and evaluation of antimicrobial activities of some substituted styryl 4-piperidinophenyl ketones. Indian J. Chem. Sec. B, vol. 58, no. 10, 2019, pp. 1131-1148
  • [5] T. Kalliokoski, C. Kramer, A. Vulpetti and P. Gedeck, Comparability of Mixed IC50 Data – A Statistical Analysis, PLoS ONE, vol. 8, no.4, 2013, pp. e61007. doi:10.1371/journal.pone.0061007
  • [6] C.G. Swain and E.C. Lupton Jr., Field and resonance components in substituent effects. J. Am. Chem. Soc. Vol. 90, 1968, pp. 4328-4337.
  • [7] Y. Tsuno, Y. Kusuyama, M. Sawada, T. Fujii and Y.Yukawa. The Substituent Effect. VIII. Solvolysis of m- and p-Substituted alpha-methylbenzyl chlorides. Bull. Chem. Soc. Jpn. Vol. 48, no. 11, 1975, pp. 3337-3346.
  • [8] I. Muthuvel, G. Thirunarayanan and S. Manikandan, FT-IR, 1H and 13C NMR QSAR and molecular docking study on some (E)-2-(2-((aryl)(phenyl)methylene) hydrazinyl)benzo[d]thiazoles. World Scientific News, 131 (2019) 54-74
  • [9] IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). Online version (2019-) created by S. J. Chalk. ISBN 0-9678550-9-8.
  • [10] S. Balaji, M. Rajarajan, R. Vijayakumar, V. Manikandan, R. Senbagam, G. Vanangamudi and G. Thirunarayanan, Synthesis, evaluation of substituent effect and antimicrobial activities of substituted (E)-1-(3-bromo-4-morpholinophenyl)-3-phenylprop-2-en-1-one compounds. Orbital: The Electronic J. Chemistry, vol. 9, no. 1, 2017, pp. 1-17
  • [11] G. Thirunarayanan and G. Vanangamudi, Synthesis, spectral studies, antimicrobial and insect antifeedant activities of some substituted styryl 4’-fluorophenyl ketones. Arabian J. Chem. Vol. 7, 2014, pp. 1055-1064.
  • [12] P. Mayavel, K. Thirumurthy, S. Dineshkumar and G. Thirunarayanan, SiO2-H3PO4 catalyzed condensation of amines and aldehydes: solvent-free synthesis of some E-imines, spectral correlations of (E)-N-(substituted benzylidene)-1-benzylpiperidin-4-amines and XRD structure of (E)-N-(4-nitrobenzylidene)-1-benzylpiperidin-4-amine. Indian J. Chem. Sec. B. vol. 54, no. 6, 2015, pp. 779-790.
  • [13] S. P. Sakthinathan, G. Vanangamudi and G. Thirunarayanan, Synthesis, spectral studies and antimicrobial activities of some 2-naphthyl pyrazoline derivatives. Spectrochim. Acta, vol. 95 A, 2012, pp. 693-700.
  • [14] G. Thirunarayanan, V. Sathiyendiran, R. Arulkumaran, R. Sundararajan, R. Manikandan and G. Vanangamudi, Assessment of substituent effects on β-naphthyl based isoxazoles by IR and NMR spectra. World Scientific News 9 (2015) 46-69.
  • [15] G. Thirunarayanan and V. Renuka, Solid SiO2-H3PO4 is an efficient catalyst for cyclization of enones under solvent-free condition: synthesis and antimicrobial activities of some oxazine derivatives. J. Chil. Chem. Soc. vol. 59, no. 3, 2014, pp. 2574-2581.
  • [16] J. Chakkaravarthy, G. Thirunarayanan and I. Muthuvel, Application of Hammett equation on spectroscopic data of some aryl sulphonamides. J. Adv. Sci. Res. Vol. 10, no. 3, 2019, pp. 196-200.
  • [17] G. Thirunarayanan, Spectral Quantitative Structure activity relationships in 3-(substituted phenyl) bicyclo[2.2.1]hept-5-en-2-yl-(pyrene-1-yl) methanone derivatives. World Scientific News, vol. 50, 2016, pp. 94-74.
  • [18] C. Mihai, A. v. Kravchuk, M.D. Tsai and K. S. Bruzik, Application of Brønsted-type LFER in the study of the phospholipase C mechanism. J. Am. Chem. Soc. Vol. 125, no. 11, 2003, pp. 3236-3242.
  • [19] M. J. D’Souza, J. A. Knapp, G.A. Fernandez-Bueno and D. N. Kevill, Use of Linear Free Energy Relationships (LFERs) to Elucidate the Mechanisms of Reaction of a γ-Methyl-β-alkynyl and an ortho-Substituted Aryl Chloroformate Ester. Int. J. Mol. Sci. vol. 13, 2012, pp. 665-682.
  • [20] R. J. Mullins, A. Vedernikov and R. Viswanathan, Competition Experiments as a Means of Evaluating Linear Free Energy Relationships. J. Chem. Educ. vol. 81, 2004, pp. 1357-1361.
  • [21] S. Endo and G. Kai-Uwe, Applications of Polyparameter Linear Free Energy Relationships in Environmental Chemistry. Environ. Sci. Technol. Vol. 48, no. 21, 2014, pp. 12477-12491.
  • [22] Advances in Linear Free Energy Relationships, N. B. chapman and J. S. Shorter Eds, Plenum Press, London 1972.
  • [23] E. N. Bess and M.S. Sigman, Book Editor(s): Prof. Dr. Mathias Christmann , Prof. Dr. Stefan Bräse, Linear Free Energy Relationships (LFERs) in Asymmetric Catalysis - Asymmetric Synthesis II - Wiley Online Library, January 2013
  • [24] G. Thirunarayanan and K. Ranganathan, SAR Analysis of some antioxidant potent (E)-2-propen-1-non-(1-(2-phenothiazenyl))-3-pheyl compounds, International Conference on Cutting Edge Research in Chemical Sciences and Workshop on Radioactivity CERICS- 2019, 19-20th September 2019, Organized by PG and Research Department of Chemistry, Poombuhar College (A), Melayur-629 107, OP. 34, pp. 25-26.
  • [25] K. G. Sekar, P. Janaki, I. Muthuvel, R. Markandan and G. Thirunarayanan, Synthesis and pharmacological evaluation of 3-(1-naphthyl)-1-substituted phenyl chalcones as potent antimicrobial agents. J. Adv. Sci. Res. vol. 11, 2020, pp. 77-82.
  • [26] D. N. Dhar and R. K. Singh, Absorption spectra of some chalcones-III. J. Indian Chem. Soc. Vol. 9, no. 3, 1972, pp. 241-244.
  • [27] Y. B. Vibhute, Synthesis and antimicrobial activities of some halo chalcones and flavanones. J. Indian Chem. Soc. Vol. 53, no. 7, 1976, pp. 736-738
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