Calix[4]pyrroles: Old yet new anion-binding agents

Journal of the American Chemical Society

Volumn 118, Issue 21, 1996, Pages 5140-5141

  Gale, Philip A ^a   Sessler, Jonathan L ^a   Král, Vladimír ^a   Lynch, Vincent ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; IONS; MOLECULAR STRUCTURE; ORGANIC COMPOUNDS;

ANION BINDING; CALIXPYRROLES; CHELATING AGENTS; MOLECULAR RECOGNITION CHEMISTRY; STABILITY CONSTANTS;

AGENTS;

BROMIDE; CALIXARENE; CHLORIDE; FLUORIDE; IODIDE; PORPHYRINOGEN; PYRROLE DERIVATIVE; SODIUM DIHYDROGEN PHOSPHATE; TETRABUTYLAMMONIUM;

ANION TRANSPORT; ARTICLE; BINDING AFFINITY; CHEMICAL BINDING; CRYSTAL STRUCTURE; MOLECULAR RECOGNITION; PROTEIN CONFORMATION; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

EID: 15844390725     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960307r     Document Type: Article

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32. w = 0.132, goodness of fit = 0.999 for 290 parameters.
33. w = 0.141, goodness of fit = 0.995 for 424 parameters.
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35. w = 0.246, goodness of fit = 1.224 for 478 parameters.
36. w = 0.171, goodness of fit = 1.029 for 152 parameters.
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39. Receplor-to-anion stoichiometries were determined from molar-ratio plots (as opposed to simple curve-fitting procedures; cf. the supporting information).
40. 1H NMR titrations were carried out with the starting concentration of receptor at 10 mM. In order to discount aggregation effects caused by hydrogen bonding between dihydrogen phosphate anions in solution, a repeat titration at a starting concentration of 100 mM 1 was carried out; it gave concordant results. Similarly, a titration involving fluoride anion but with a starting concentration of 1.0 mM 1 was carried out. It gave results identical within error to those obtained from titrations carried out with an initial receptor concentration of 10 mM.
41. Preliminary structural data confirms that the calixpyrrole 1 will bind methanol in the solid state.
42. Preliminary mass spectrometric evidence confirms that calix[5], [6], and [7]pyrroles are formed in trace quantities under certain conditions (see the supporting information).