2-Aminomethyl-18-crown-6,95%

2-Aminomethyl-18-crown-6 for the Synthesis and Cation Complexation Study of a Gossypol Schiff Base

Przybylski P, et al. Journal of Molecular Structure, 2004, 699(1-3), 65-77.

2-Aminomethyl-18-crown-6 was experimentally applied as a key amine precursor for the synthesis of a gossypol-based Schiff base (GSCC) designed for selective monovalent cation recognition. The Schiff base was prepared via condensation of gossypol with 2-aminomethyl-18-crown-6, followed by systematic complexation with H⁺, Li⁺, Na⁺, K⁺, Rb⁺, and Cs⁺ using perchlorate salts in acetonitrile/ethanol media. Complex formation and stoichiometry were rigorously characterized by ESI-MS, ^1H NMR, and FT-IR spectroscopy, supported by PM5 semiempirical calculations. The crown ether moiety derived from 2-aminomethyl-18-crown-6 enabled size-dependent coordination, yielding 1:2 complexes with all monovalent cations and unique 1:4 complexes with Li⁺ and Na⁺. These results demonstrate the experimental utility of 2-aminomethyl-18-crown-6 in constructing multifunctional ligands for cation binding studies.