Calix[n]bipyrroles: Synthesis, characterization, and anion-binding studies

Angewandte Chemie - International Edition

Volumn 42, Issue 20, 2003, Pages 2278-2281

  Sessler, Jonathan L ^a   An, Deqiang ^a   Cho, Won Seob ^a   Lynch, Vincent ^a  

^a The University of Texas at Austin   (United States)

Author keywords

Anions; Calixpyrroles; Halides; Macrocycles; Supramolecular chemistry

Indexed keywords

COMPLEXATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

ISOTHERMAL TITRATION CALORIMETRY;

NEGATIVE IONS;

ANION; CALIX[N]BIPYRROLE DERIVATIVE; MACROCYCLIC COMPOUND; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; COMPLEX FORMATION; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANIONS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PYRROLES; SOLVENTS;

EID: 0037981627     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200350941     Document Type: Article

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41. - ion. Specifically, we believe that the corresponding incommensurate binding geometry, as evidenced more by the unfavorable Cl-H-N angles seen in the solid state (ranging from 147.5-175.5°) than by the Cl⋯H-N hydrogen bond lengths, outweighs in an adverse sense the binding advantage that an increased number of hydrogen bonds would be expected to impart, at least in this relatively less polar solvent. This is not the case in DMSO. Here, the increased number of hydrogen-bond donor groups serves to overcome competition from the solvent, with the net result that stronger binding of a chloride anion is displayed by 10 relative to 1 in DMSO.