Torandsynthese durch Trimerisierung — neue Rezeptoren für Guanidinium

Abstract

Das größte bisher bekannte Cycloarenderivat, der Torand 1, ist durch CsOH‐vermittelte Cyclotrimerisierung überraschend gut zugänglich. 1 liegt nach Macromodel‐Rechnungen fast planar vor und bindet Guanidinium unter Bildung von sechs nahezu idealen Wasserstoffbrücken bei nur geringer Konformationsänderung: Die UV‐Spektren des Torands und seines Guanidinium‐Komplexes stimmen nahezu überein.magnified image

Cation-Promoted Hierarchical Formation of Supramolecular Assemblies of Self-Organized Helical Molecular Components

“…In view of the large dipole moment of napy (4.1 D in benzene, 25 °C),11 the helical entity A should present a very polar interior and be able to bind a variety of cationic species, which themselves could thereafter promote helix aggregation. Acyclic and macrocyclic structures containing rigidly maintained napy units have been described and found to bind guanidinium ions 12…”

A Small-Molecule Guanidinium Receptor: The Arginine Cork

“…host hexagonal lattice distance (determined by CÀN and CÀC covalent bonds), which bear an approximate 2:1 relationship. Previously reported hexagonal lattice receptors, including a guanidinium-binding torand, [19] are neutral molecules with hydrophobic n-alkyl side chains. Such compounds are useful as extractants and membrane transport agents, [17,18] but their poor water solubilities limit homogeneous binding studies to organic solvents.…”

Molecular recognition of creatinine

“…*H NMR (CDCI3): 7.8 (s, br., 2 H, NHj), 3.67 (s, 2 H, (CO)CH2), 3.44-3.55 (m, CH), 1.6-1.1 (m, 24 H, (CH2)6CH3), 0.87 (t,} = 7, 6 H, CH3). Elemental analysis: Calculated for C18H35N30 (309.50): 69.58% C, 11.40% H, 13.58% N. Found: 69.87% C, 11.38% H, 13.47% N. EI-MS: 311 ((M+2)+, 10), 310 ((M+l)+, 54), 309 (M+, 61), 280 (7), 267 (5), 266 (9), 252 (11), 238 (7), 225 (9), 224 (32), 212 (7), 211 (60), 210 (92), 182 (9), 168 (6), 154 (6), 141 (9), 140 (24), 127 (9), 126 (30), 113 (22), 112 (6), 101 (5), 100 (100), 99 (55), 98 (14), 97 (7), 84 (6), 83 (9), 72 (5), 71 (9), 70 (9), 69 (16), 57 (13), 56 (12), 55 (24), 43 (23), 42 (18), 41 (20), 30 (10), 29 (8), 28 (5), 18 (7).…”