Solution and X-Ray Crystal Structures of the Di- and Tetra-allyl Ether of tert- utylcalix[4]arene View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2003-04

AUTHORS

Silvia Stumpf, Gudrun Goretzki, Kerstin Gloe, Karsten Gloe, Wilhelm Seichte, Edwin Weber, Jan W. Bats

ABSTRACT

The di- and tetra-allyl ethers of tert-butylcalix[4]arene 1 and 2 have been prepared by alkylation of tert-butylcalix[4]arene with allyl bromide and K2CO3 using different reaction times. Solution 1H NMR measurement of the di-allyl ether 1 and X-ray crystal structures of the complexes of 1 with chloroform (1a) or methanol (1b) indicate the cone conformation of 1 in which intramolecular hydrogen bonding can be maximized. The crystalline state conformers 1a and 1b are distorted in different grades depending on the solvent. While methanol is incorporated in the macrocycle, chloroform molecules do not occupy the cage. The solution 1H NMR spectra of tetra-allyl ether 2 show the co-existence of the cone and partial cone conformation. The partial cone conformer of 2 was investigated by X-ray crystallography. In this compound hydrogen bonding is not existent. The conformer distribution is likely affected by steric and template effects. More... »

PAGES

225-233

Identifiers

URI

http://scigraph.springernature.com/pub.10.1023/a:1024568408356

DOI

http://dx.doi.org/10.1023/a:1024568408356

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1035110216


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