TY - JOUR
T1 - New Lariat Ether Carboxylic and Hydroxamic Acids
T2 - Synthesis and Lanthanide Ion Complexation
AU - Elshani, Sadik
AU - Noriyuki, Randal
AU - Wai, Chien M.
AU - Natale, N. R.
AU - Bartsch, Richard A.
PY - 1998
Y1 - 1998
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0001347279&partnerID=8YFLogxK
U2 - 10.1002/jhet.5570350416
DO - 10.1002/jhet.5570350416
M3 - Article
AN - SCOPUS:0001347279
SN - 0022-152X
VL - 35
SP - 875
EP - 885
JO - Journal of Heterocyclic Chemistry
JF - Journal of Heterocyclic Chemistry
IS - 4
ER -