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A Calix[6]arene Dimer Linked Through Amino Acid Hydrogen Bond Interactions
Author(s) -
Rincón Ana M.,
Prados Pilar,
de Mendoza Javier
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200202)2002:4<640::aid-ejoc640>3.0.co;2-u
Subject(s) - chemistry , dimer , hydrogen bond , calixarene , chloroform , gel permeation chromatography , molecular dynamics , molecular recognition , nuclear magnetic resonance spectroscopy , monomer , polymer chemistry , permeation , stereochemistry , organic chemistry , computational chemistry , molecule , polymer , membrane , biochemistry
A calix[6]arene containing three leucine residues at the lower rim dimerizes in apolar solvents with the formation of up to eighteen hydrogen bonds, giving rise to a self‐assembled molecular capsule. The dimerization in chloroform was conformed by NMR spectroscopy and gel permeation chromatography, as well as by molecular mechanics and dynamics calculations. The highly flexible structure is unable to encapsulate guests of complementary size, probably because six methoxy groups and one of the leucyl residues permanently occupy the cavity.