Synthesis, Solid and Solution Studies of Paraquat Dichloride Calixarene Complexes. Molecular Modelling
DOI:
https://doi.org/10.29356/jmcs.v54i3.926Keywords:
Parent calixarenes; Pesticides; Phosphorescence; Augmented Molecular Mechanics Calculations; CONFLEX.Abstract
The interaction of the herbicide paraquat dichloride (PQ,substrate) with p-tert butylcalix[6,8]arenes (L, receptor) was investigated in both the solution and solid states. The isolated paraquat calixarene complexes were characterised by UV-visible, 1H NMR, ESI-MS, Luminescence and IR spectroscopies and elemental analysis. The stoichiometry of complexes 1 and 2 was 1:1 (1 herbicide:1 calixarene) and both revealed a biexponential luminescence decay with lifetimes depending on the size and the conformational particularity of the calixarenes. Molecular modelling suggested that both calixarenes interact with the herbicide through cation-π interaction. PQ is included in the p-tert-butylcalix[8]arene cavity, a situation favoured by its pinched conformation in polar solvent while it is partially included in the p-tert-butylcalix[6]arene cavity because of its in-out cone conformation. The theoretical results, in particular using MOPAC procedures, were in agreement with the experimental findings.
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4. Rytwo, G.; Tropp, O.; Serban, C. Appl. Clay Sci. 2002, 20, 273-282.
5. a) Monk, P. M. S.; Mortimer, R. J.; Rosseinsky, D. R. Electrochromism: Fundamental and Applications; VCH, Weinheim, 1995. b) Sliwa, W.; Bachowska, B.; Zelichowicz, N. Heterocycles 1991, 32, 2241-2273.
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F. de M.; Ferro-Flores, G.; Arteaga de Murphy, C.; Pedraza-López, M.; Hnatowich, D. J. Nucl. Med. Biol. 2003, 30, 605-615.
8. a) Cerichelli, G.; Mancini, G. Langmuir 2000, 16, 182-187. b) Dalla Cort, A.; Mandolini, L.; Mencarelli, P.; Schiaffino L. Supramol. Chem. 2001, 13, 313-323. c) Dalla Cort, A.; Nissinen, M.,; Mancinetti, D.; Nicoletti, E.; Mandolini, L.; Rissanen, K. J. Phys. Org. Chem. 2001, 14, 425-431. d) Bernardo, A. R.; Lu, T.; Córdova, E.; Zhang, L.; Gokel, G. W.; Keifer, A. E. J. Chem. Soc. Dalton Trans. 1994, 529-530. e) Hwang, G. T.; Kim, B. H.; Tetrahedron 2002, 58, 9019-9028.
9. a) Gibson, H. W.; Nagvekar, D. S.; Delaviz, Y.; Bryant, W. S Can. J. Chem. 1998, 76, 1429-1436; b) Huang, F.; Gantzel, P.; Nagvekar, D. S.; Rheingold, A. L.; Gibson, H. W. Tetrahedron Lett. 2006, 47, 7841-7844; c) Han, T.; Chen, C.-F. Org. Lett. 2006, 8, 1069-1072. d) Huang, F.; Gibson, H. W.; Bryant W. S.; Nagvekar, D. S.; Fronczek F. R. J. Am .Chem. Soc. 2003, 125, 9367-9371; e) Bryant, W. S. ; Jones, J. W.; Mason, P. E.; Guzei, I. A.; Rheingold, A. L.; Nagvekar, D. S.; Gibson, H. W. Org. Lett. 1999, 1, 1001-1004. f) Huang, F.; Guzei, I. A.; Jones, J. W.; Gibson, H. W. Chem. Commun. 2005, 1693-1695.
10. a) Arduini, A.; Ciesa, F.; Fragassi, M.; Pochini, A.; Secchi, A. Angew. Chem. Int. Ed. 2005, 44, 278-281. b) Ugozzoli, F.; Massera, C.; Arduini, A.; Pochini, A.; Secchi, A. CrystEngComm, 2004, 6, 327-332. c) Credi, A.; Dumas, S.; Silvi, S.; Ventura, M.; Arduini, A.; Pochini, A.; Secchi, A. J. Org. Chem. 2004, 69,
5881-5887. d) Arduini, A.; Calzavacca, F.; Pochini, A.; Secchi, A. Chem. Eur. J. 2003, 9, 793-799. e) Arduini, A.; Ferdani, R.; Pochini, A.; Secchi, A.; Ugozzoli, F. Angew. Chem. Int. Ed. 2000, 39, 3453-3456. f) Arduini, A.; Bussolati, R.; Credi, A.; Pochini, A.; Secchi, A.; Silvi, S.; Ventura, M. Tetrahedron 2008, 64, 8279-8286.
11. a) Forster, M.; Girling, R. B.; Hester, R. E. J. Raman Spectrosc. 1982, 12, 36-48. b) Socrates, G. Infrared and Raman Characteristic Groups Frequencies, Tables and Charts, John Wiley and Sons LTD, England, 2005. c) Williams, D. H.; Fleming, I. Spectroscopic Methods in Organic Chemistry, Mc Graw Hill Book Company, UK, Limited. 1980.
12. Gutsche, C. D.; Bauer, L. J. J. Am. Chem. Soc. 1985, 107, 6052- 6059.
13. Bünzli, J.-C. in Lanthanide Probes in Life, Chemical and Earth Sciences. Theory and Practice, Chapter 7, Eds. Bünzli, J.-C. G.; Choppin, G. R. Elsevier Science Publications B.V., Amsterdam, 1989, pp. 219-293.
14. a) Ramírez, F. M.; Varbonov, S.; Cécile, C.; Muller, G.; Fatin-
Rouge, N.; Scopelliti, R.; Bünzli, J.-C. G. J. Chem. Soc. Dalton Trans. 2002, 4505-4513 ; b) Ramírez, F. M.; Charbonnière, L.; Muller, G.; Bünzli, J.-C. G. Eur. J. Inorg. Chem. 2004, 2348-2355.
15. Goto, H.; Osawa, E. J. Chem. Soc. Perkin Trans. 2 1993, 187-198.
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