π-Methyl interactions and p-tertbutylcalix[4]arene-guest stability: NMR and crystallographic studies of cyclohexane and n-pentane inclusion compounds

Supramolecular Chemistry

Volumn 7, Issue 2, 1996, Pages 143-145

  Brouwer, Eric B ^a,b   Enright, Gary D ^b   Ripmeester, John A ^a,b  

^a CARLETON UNIVERSITY   (Canada)

^b NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000148272     PISSN: 10610278     EISSN: None     Source Type: Journal    
DOI: 10.1080/10610279608035189     Document Type: Article

References (18)

1. Issued as NRCC No. 39076 (to be supplied in proof).
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7. Perrin, M.; Oehler, D. in Calixarenes, Vicens, J. and Bohmer, V. (Eds.), Kluwer, Dordrecht, 1990, p. 65.
8. Ungaro, R.; Arduini, A.; Casnati, A.; Ori, O.; Pochini, A.; Ugozzoli, F. in Computational Approaches in Supramolecular Chemistry, NATO ASI Series C426 Wipff, G. (Ed.), Kluwer, Dordrecht, 1994, p. 277.
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11. McKervey, M. A.; Seward, E. M.; Ferguson, G.; Ruhl, B. L. J. Org. Chem. 1986, 51, 3581; Arduini, A.; Ghidini, E.; Pochini, A.; Ungaro, R.; Andreetti, G. D.; Calestani, G.; Ugozzoli, F. J. Incl. Phenom. 1988, 6, 119; Harrowfield, J. M.; Ogden, M. I.; Richmond, W. R.; White, A. H. 1991, 1159; Steed, J. W.; Juneja, R. K.; Burkhalter, R. S.; Atwood, J. L. J. Chem. Soc., Chem. Commun. 1994, 2205.
12. McKervey, M. A.; Seward, E. M.; Ferguson, G.; Ruhl, B. L. J. Org. Chem. 1986, 51, 3581; Arduini, A.; Ghidini, E.; Pochini, A.; Ungaro, R.; Andreetti, G. D.; Calestani, G.; Ugozzoli, F. J. Incl. Phenom. 1988, 6, 119; Harrowfield, J. M.; Ogden, M. I.; Richmond, W. R.; White, A. H. 1991, 1159; Steed, J. W.; Juneja, R. K.; Burkhalter, R. S.; Atwood, J. L. J. Chem. Soc., Chem. Commun. 1994, 2205.
13. McKervey, M. A.; Seward, E. M.; Ferguson, G.; Ruhl, B. L. J. Org. Chem. 1986, 51, 3581; Arduini, A.; Ghidini, E.; Pochini, A.; Ungaro, R.; Andreetti, G. D.; Calestani, G.; Ugozzoli, F. J. Incl. Phenom. 1988, 6, 119; Harrowfield, J. M.; Ogden, M. I.; Richmond, W. R.; White, A. H. 1991, 1159; Steed, J. W.; Juneja, R. K.; Burkhalter, R. S.; Atwood, J. L. J. Chem. Soc., Chem. Commun. 1994, 2205.
14. p-tert-butylcalix[4]arene (238 mg, 0.366 mmol) was dissolved in 3-nitrotoluene (3 mL) in a small vial which was placed inside a larger, capped vial containing cyclohexane (3 mL) at room temperature. After 2 d, the crystal-containing solution in the inner vial was filtered yielding colourless crystals of 1 (179 mg, 0.244 mmol, 67% yield); 2 was prepared in a similar fashion. Microcrystalline powders of 1 and 2 may also be prepared by mixing p-tert-butylcalix[4]arene with the appropriate hydrocarbon at low heat for 1 h, followed by filtration. Both 1 and 2 are stable (with respect to loss of guest) for several weeks at room temperature.
15. 14
16. Schneider, H.-J.; Guttes, D.; Schneider, U. J. Am. Chem. Soc. 1988, 110, 6449.
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18. Gabe, E. J.; Le Page, Y.; Charland, J. P.; Lee, F. L.; White, P. S. J. Appl. Cryst., 1989, 22, 384.