Double partial cone conformation for Na{sub 8}(calix[6]arene sulfonate){center_dot}20.5H{sub 2}O and its parent acid

Journal Article · Wed Sep 09 04:00:00 EDT 1992 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/ja00045a035· OSTI ID:539442

Atwood, J L; Juneja, R K; Orr, G W ^[1]

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1. Univ. of Alabama, Tuscaloosa, AL (United States); and others

The chemistry of calixarenes has recently become a very active area of endeavor. Of the numerous stimulating findings to appear thus far in the literature, one of the most intriguing concerns the discovery of certain uranophiles by Shinkai. It was reported that calix[5]arene sulfonate, calix[6]arene sulfonate, and the two corresponding derivatives substituted at the base by carboxymethoxy groups, 1 with R{prime} = CH{sub 2}COOH, exhibited stability constants for the uranyl ion of K = 10{sup 18.4-19.2}. Indeed, in competition experiments these calixarenes showed selectivity factors of 10{sup 12-17} for uranyl over the Ni{sup 2+}, Zn{sup 2+}, and Cu{sup 2+} ions. This selectivity was attributed to a moderately rigid calix[6]arene structure which was preorganized to match the rather unusual pseudoplanar hexacoordination needs of the UO{sub 2}{sup 2+} ion. However, on the basis of this study this premise appears untenable. Considering the importance of the above mentioned findings, the structural chemistry of derivatives of calix[6]arene has been slow to develop. In the available selection it is difficult to find general conformational features, apart from the elliptical cone conformation exhibited by the parent p-tert-butycalix[6]arene. Since our group has found a rich and often surprising inclusion chemistry for calix[4]arene sulfonates, we decided to investigate the structure of calix[6]arene sulfonate and its alkali metal salts. 28 refs., 1 fig.

• Sponsoring Organization: USDOE
• DOE Contract Number: W-7405-ENG-36
• OSTI ID: 539442
• Journal Information: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 19 Vol. 114; ISSN JACSAT; ISSN 0002-7863
• Country of Publication: United States
• Language: English

Related Subjects

36 MATERIALS SCIENCE
40 CHEMISTRY
ALKALI METAL COMPOUNDS
CHEMICAL BONDS
CONFORMATIONAL CHANGES
GEOMETRY
HYDROLYSIS
IONS
MOLECULAR STRUCTURE
QUALITATIVE CHEMICAL ANALYSIS
SALTS
STRUCTURAL CHEMICAL ANALYSIS
SULFONATES