Conformation of hexahydroxycalix[6]arene

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 7180-7184

  Van Hoorn, Willem P ^a   Van Veggel, Frank C J M ^a   Reinhoudt, David N ^a  

^a UNIVERSITY OF TWENTE   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000045570     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960865o     Document Type: Article

References (27)

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12. van Hoorn, W. P.; Briels, W. J.; van Duynhoven, J. P. M.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Submitted for publication.
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18. Fischer, S. Manuscript in preparation.
19. The SCM algorithm does not affect the calculated saddle pointis).
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23. Only two (the 4:3 and 1:6 OH-OH distances) of the 30 hydroxy-hydroxy and hydroxy-methylene distance constraints are violated in a winged cone. The pinched and winged cone conformations are also indistinguishable when looking at the methylene-aromatic distances.
24. 6,22 Both of these mechanisms cannot be modeled adequately by force field calculations and are therefore not dealt with here.
25. Kim, Y. J. Am. Chem. Soc. 1996, 118, 1522.
26. For the winged Cone, there is a possible cooperative effect of combining pseudorotation with inversion in the following process: winged cone →→ pseudorotated pinched cone → inverted pinched cone → inverted winged cone However, the rate-limiting step is now one of the winged/pinched cone exchanges (Figure 2c). The combined pseudorotation/inversion process of the winged cone showed no cooperativity, the pseudoration and inversion proceeded separately (data not shown).
27. 6,22 J. Org. Chem. 1996, 61, 7185-7188