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

Abstract

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 investigatemore » the structure of calix[6]arene sulfonate and its alkali metal salts. 28 refs., 1 fig.« less

Authors:
; ;  [1]
  1. Univ. of Alabama, Tuscaloosa, AL (United States); and others
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
539442
DOE Contract Number:  
W-7405-ENG-36
Resource Type:
Journal Article
Journal Name:
Journal of the American Chemical Society
Additional Journal Information:
Journal Volume: 114; Journal Issue: 19; Other Information: PBD: 9 Sep 1992
Country of Publication:
United States
Language:
English
Subject:
40 CHEMISTRY; 36 MATERIALS SCIENCE; SULFONATES; GEOMETRY; MOLECULAR STRUCTURE; QUALITATIVE CHEMICAL ANALYSIS; HYDROLYSIS; CONFORMATIONAL CHANGES; STRUCTURAL CHEMICAL ANALYSIS; ALKALI METAL COMPOUNDS; IONS; SALTS; CHEMICAL BONDS

Citation Formats

Atwood, J L, Juneja, R K, and Orr, G W. Double partial cone conformation for Na{sub 8}(calix[6]arene sulfonate){center_dot}20.5H{sub 2}O and its parent acid. United States: N. p., 1992. Web. doi:10.1021/ja00045a035.
Atwood, J L, Juneja, R K, & Orr, G W. Double partial cone conformation for Na{sub 8}(calix[6]arene sulfonate){center_dot}20.5H{sub 2}O and its parent acid. United States. doi:10.1021/ja00045a035.
Atwood, J L, Juneja, R K, and Orr, G W. Wed . "Double partial cone conformation for Na{sub 8}(calix[6]arene sulfonate){center_dot}20.5H{sub 2}O and its parent acid". United States. doi:10.1021/ja00045a035.
@article{osti_539442,
title = {Double partial cone conformation for Na{sub 8}(calix[6]arene sulfonate){center_dot}20.5H{sub 2}O and its parent acid},
author = {Atwood, J L and Juneja, R K and Orr, G W},
abstractNote = {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.},
doi = {10.1021/ja00045a035},
journal = {Journal of the American Chemical Society},
number = 19,
volume = 114,
place = {United States},
year = {1992},
month = {9}
}