New Lariat Ether Carboxylic and Hydroxamic Acids: Synthesis and Lanthanide Ion Complexation

Sadik Elshani, Randal Noriyuki, Chien M. Wai, N. R. Natale, Richard A. Bartsch

Research output: Contribution to journalArticlepeer-review

Abstract

Twenty-six new lariat ether carboxylic and hydroxamic acids based upon dibenzo-13-crown-4, dibenzo-14-crown-4, dibenzo-16-crown-5 and dibenzo-19-crown-6 ring systems are synthesized and the solid-state structure for a dibenzo-19-crown-6 lariat ether hydroxamic acid is determined. The efficiency and selectivity for lanthanide ion extraction into chloroform by these proton-ionizable lariat ethers is strongly influenced by the crown ether ring size, lipophilic group attachment site and identity of the acidic function. In general, the lariat ether hydroxamic acids were more efficient and selective lanthanide ion extractants than the corresponding lariat ether carboxylic acids. The 1H nmr and ir binding studies indicate that both the macrocyclic polyether unit and the proton-ionizable group are involved in lanthanide ion complexation.

Original languageEnglish
Pages (from-to)875-885
Number of pages11
JournalJournal of Heterocyclic Chemistry
Volume35
Issue number4
DOIs
StatePublished - 1998

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