Copyright (c) 2023 PARATHARAJ SENTHILKUMAR, Krishnan Radhakrishnan
This work is licensed under a Creative Commons Attribution 4.0 International License.
Effect of Substituent on the 13C NMR Chemical Shifts of Substituted 26-Member [2+2] Macrocyclic Compounds
Corresponding Author(s) : Paratharaj Senthilkumar
Asian Journal of Chemistry,
Vol. 36 No. 1 (2024): Vol 36 Issue 1, 2024
Abstract
A series of substituted symmetrical 14,15,34,35,94,95,114,115-octamethoxy-2,10-bis(4-methoxyphenyl)-4,8,12,16-tetraaza-1,3,9,11(1,2),6,14(1,4)-hexabenzenacyclohexadecaphane-4,7,12,15-tetraene compounds (macrocyclic compounds) have been prepared by condensation of various substituted benzaldehyde with 1,2-dimethoxy benzene followed by nitration, reduction and cyclization with terephthaldehyde. Isolated substituted compounds were characterized by UV, IR, NMR and Mass spectrometric technics. Investigation of substituents effect and mode of transmission of electronic effects have been carried out by 13C NMR chemical shifts measurement and correlated it with LFER parameters in substituted macrocyclic compounds.
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- E. Rosta and A. Warshel, J. Chem. Theory Comput., 8, 3574 (2012); https://doi.org/10.1021/ct2009329
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- K. Radhakrishnan, P. Senthilkumar, P.K. Manikandan and U.K. Ray, J. Adv. Sci. Res., 12, 198 (2021).
- P. Senthilkumar, K. Radhakrishnan and P.K. Manikandan, World J. Pharm. Res., 11, PP1103 (2022).
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- G. Thirunarayanan, K.G. Sekar and R.L. Narayanan, Int. Lett. Chem. Phys. Astron., 32, 88 (2014); https://doi.org/10.56431/p-4kg378
- M. Rajarajan, R. Senbagam, V. Vijayakumar, V. Manikandan, S. Balaji, G. Vanangamudi and G. Thirukumaran, World Sci. News, 9, 155 (2015).
- G. Thirunarayanan, M. Gopalakrishnan and G. Vanangamudi, Spectrochim. Acta A Mol. Biomol. Spectrosc., 67, 1106 (2007); https://doi.org/10.1016/j.saa.2006.09.034
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References
E. Rosta and A. Warshel, J. Chem. Theory Comput., 8, 3574 (2012); https://doi.org/10.1021/ct2009329
J. Shorter, Correlation Analysis in Organic Chemistry, An Introduction to Linear Free Energy Relationship, London, p. 119 (1973).
D. Iguchi, D. Ravelli, R. Erra-Balsells and S.M. Bonesi, Molecules, 25, 2061 (2020); https://doi.org/10.3390/molecules25092061
C. Hansch, A. Leo and R.W. Taft, Chem. Rev., 91, 165 (1991); https://doi.org/10.1021/cr00002a004
A. Ikezaki, T. Ikeue and M. Nakamura, Inorg. Chim. Acta, 335, 91 (2002); https://doi.org/10.1016/S0020-1693(02)00819-8
N.Y. Gorobets, S.A. Yermolayev, T. Gurley, A.A. Gurinov, P.M. Tolstoy, I.G. Shenderovich and N.E. Leadbeater, J. Phys. Org. Chem., 25, 287 (2012); https://doi.org/10.1002/poc.1910
C. Bustos, L. Alvarez-Thon, E. Molins, I. Moreno-Villoslada, G. VallejosContreras, C. Sánchez, X. Zarate, D. Mac-Leod Carey and E. Schott, J. Mol. Struct., 1171, 349 (2018); https://doi.org/10.1016/j.molstruc.2018.05.088
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M.B. Smith and J. March, March’s Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, Wiley: Hoboken, NJ, USA, edn, 6, p. 401 (2007).
F.A. Carey and R.J. Sundberg, Advanced Organic Chemistry, Part A: Structure and Mechanisms, Springer: Berlin/Heidelberg, Germany, edn. 5, p. 335 (2007).
F.A. Carroll, Perspectives on Structure and Mechanism in Organic Chemistry; John Wiley & Sons: Hoboken, NJ, USA, p. 366 (1998).
J.H. Markgraf, L. Hong, D.P. Richardson and M.H. Schofield, Magn. Reson. Chem., 45, 985 (2007); https://doi.org/10.1002/mrc.2082
H.S. Lee, J.S. Yu and C.K. Lee, Bull. Korean Chem. Soc., 30, 2351 (2009); https://doi.org/10.5012/bkcs.2009.30.10.2351
N. Kalyanasundaram, S.P. Sakthinathan, R. Suresh, D. Kamalakkannan, S. John Joseph, G. Vanangamudi and G. Thirunarayanan, Int. Lett. Chem. Phys. Astron, 28, 23 (2014); https://doi.org/10.56431/p-4z1nao
D.J. Craik and R.T.C. Brownlee, Prog. Phys. Org. Chem., 14, 1 (1983); https://doi.org/10.1002/9780470171936.ch1
N.B. Chapman and J. Shorter, Advances in Linear Free Energy Relationships, Plenum: London (1972).
L.P. Hammett, Physical Organic Chemistry, McGraw Hill Book Company, Inc., New York, Chapter VII, (1970).
K. Radhakrishnan, P. Senthilkumar, P.K. Manikandan and U.K. Ray, J. Adv. Sci. Res., 12, 198 (2021).
P. Senthilkumar, K. Radhakrishnan and P.K. Manikandan, World J. Pharm. Res., 11, PP1103 (2022).
R. Arulkumaran, V. Manikandan and G. Thirunarayanan, World Sci. News, 80, 235 (2017).
R. Arulkumaran, V. Manikandan, P. Christhuraj and G. Thirunarayanan, World Sci. News, 62, 93 (2017).
G. Thirunarayanan, K.G. Sekar and R.L. Narayanan, Int. Lett. Chem. Phys. Astron., 32, 88 (2014); https://doi.org/10.56431/p-4kg378
M. Rajarajan, R. Senbagam, V. Vijayakumar, V. Manikandan, S. Balaji, G. Vanangamudi and G. Thirukumaran, World Sci. News, 9, 155 (2015).
G. Thirunarayanan, M. Gopalakrishnan and G. Vanangamudi, Spectrochim. Acta A Mol. Biomol. Spectrosc., 67, 1106 (2007); https://doi.org/10.1016/j.saa.2006.09.034
G. Thirunarayanan, Bull. Chem. Soc. Ethiop., 28, 73 (2014); https://doi.org/10.4314/bcse.v28i1.9
J.E. Arrowsmith, M.J. Cook and D.J. Hardstone, Org. Magn. Reson., 11, 160 (1978); https://doi.org/10.1002/mrc.1270110314
P. Mohandass, K. Radhakrishnan, S. Manimekalai, V. Suriyanarayanan and S. Radhakrishnan, Asian J. Res. Chem, 11, 43 (2018); https://doi.org/10.5958/0974-4150.2018.00010.X