Diaza- 18-Crown-6 Ligands Containing Two Aminophenol Side Arms: New Heterobinuclear Metal Ion Receptors.
Abstract
Three diaza-18-crown-6 ligands substituted with two aminophenol side arms were synthesized as possible heterobinuclear metal ion receptors. Bis(p-aminophenol)-substituted diaza-18-crown-6 ligand (13) was prepared by treating the diazacrown with alpha-bromo-4-nitro-o-cresol in the presence of N,N-diisopropylethylamine followed by reduction of the nitro groups. Bis(o-aminophenol)-substituted diaza-18-crown-6 ligands (11 and 12) were prepared in two steps by the aminomethylation of either an 0-nitrophenols or o-(trifluoroacetamido)phenol followed by reduction of the nitro groups or hydrolysis of the trifluoroacetamide groups. All new bisphenol-armed diazacrown ligands were purified by ultrasonication in MeOH followed by filtration and drying. Interaction of the ligands with Na(+), K(+), Ag(+), and Cu(2+) was evaluated by a calorimetric titration technique at 25 deg C in MeOH. The complexes of Ag(+) and Cu(2+) are much more stable than those of Na(+) and K(+). Heterobinuclear complexes were observed for 11-Cu(2+)- Na(+) and 12-Cu(2+)-Na(+) but not for 13-Cu(2+)-Na(+) or for 12-Cu(2+)-Ag(+).
Document Details
- Document Type
- Technical Report
- Publication Date
- Sep 30, 1999
- Accession Number
- ADA368653
Entities
People
- Jerald S. Bradshaw
- Krzysztof E. Krakowiak
- Ning Su
- Paul B. Savage
- Xian X. Zhang
Organizations
- Brigham Young University