Confinement of Amino Acids in Tetra-p-Sulfonated Calix[4]arene Bilayers

• Published in: Crystal growth & design Vol. 2; no. 3; pp. 171 - 176
• Main Authors: Atwood, Jerry L, Ness, Timothy, Nichols, Peter J, Raston, Colin L
• Format: Journal Article
• Language: English
• Published: Washington,DC American Chemical Society 01.05.2002
• Subjects: Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds; Aminoacids and peptides; Condensed matter: structure, mechanical and thermal properties; Exact sciences and technology; Organic compounds; Physics; Structure of solids and liquids; crystallography; Structure of specific crystalline solids; Pentacyclic compound; Encapsulation; Molecular structure; Chiral compound; Sulfonates; Calixarene; XRD; Experimental study; Alcohols; Macrocycle; Racemates; α-Aminoacid; Hydrogen bonds; Supramolecular structure; Temperature range 65-273 K; Cyclophane; Organic compounds; Low temperature; Adducts; Crystal structure
• ISSN: 1528-7483; 1528-7505
• DOI: 10.1021/cg0200053

Supramolecular complexes of tetra-p-sulfonated calix[4]arene and racemic (alanine, histidine, and phenylalanine) and chiral ((S)-alanine, (S)-histidine, and (S)-tyrosine) amino acids have been isolated in the solid state and their molecular structures elucidated by X-ray diffraction studies. For alanine, histidine, and phenylalanine, racemic pairs of molecules are confined in capsules of tetra-p-sulfonated calix[4]arene in an overall bilayer arrangement. The (S)-amino acid isomers for alanine and histidine, however, formed 1:1 complexes within the bilayer arrangement found for many tetra-p-sulfonated calix[4]arene complexes. For (S)-tyrosine, a π-stacked chiral pair of isomers was encapsulated by tetra-p-sulfonated calix[4]arene.