Hydrogen-bonded dimers of a thiacalixarene substituted by carbamoylmethylphosphineoxide groups at the wide rim.

Chem Commun (Camb)

Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 02660, Kyiv-94, Murmanskaya str. 5, Kiev, Ukraine.

Published: May 2006

A thiacalix[4]arene derivative bearing four carbamoylmethylphosphineoxide groups at the wide rim forms hydrogen-bonded, dimeric capsules with S8 symmetry in the crystalline state and in apolar solvents, where the inclusion of cationic guests could be proved by 1H NMR and ESI mass spectra.

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http://dx.doi.org/10.1039/b601016dDOI Listing

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A thiacalix[4]arene derivative bearing four carbamoylmethylphosphineoxide groups at the wide rim forms hydrogen-bonded, dimeric capsules with S8 symmetry in the crystalline state and in apolar solvents, where the inclusion of cationic guests could be proved by 1H NMR and ESI mass spectra.

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Conformationally rigidified tetraCMPO derivatives have been prepared from calix[4]arene bis(crown ether) 4a in which adjacent oxygens are bridged at the narrow rim by two diethylene glycol links. Acylation of the tetraamine 4c with the CMPO-active ester 5b gave the tetraphosphine oxide 6a, while the tetraphosphinate 6b and the tetraphosphonate 6c were obtained by Arbuzov reaction of tetrabromoacetamido derivative 7 with PhP(OEt)2 or P(OEt)3. The extraction ability of these CMPO derivatives was checked for selected lanthanides and actinides and compared with the analogous compounds 1b, 10b and 10d derived from calix[4]arene tetrapentyl ether.

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