SYNTHESIS OF PROTON-IONIZABLE P-NITROPHENOL-CONTAINING TETRAAZACROWN AND DIAZADITHIACROWN ETHERS FROM AN AROMATIC BUILDING-BLOCK PREPARED VIA THE EINHORN REACTION

Citation
Kj. Hu et al., SYNTHESIS OF PROTON-IONIZABLE P-NITROPHENOL-CONTAINING TETRAAZACROWN AND DIAZADITHIACROWN ETHERS FROM AN AROMATIC BUILDING-BLOCK PREPARED VIA THE EINHORN REACTION, Journal of organic chemistry, 63(14), 1998, pp. 4786-4791
Citations number
32
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
0022-3263
Volume
63
Issue
14
Year of publication
1998
Pages
4786 - 4791
Database
ISI
SICI code
0022-3263(1998)63:14<4786:SOPPTA>2.0.ZU;2-R
Abstract
A series of p-nitroanisole-containing tetraazacrown (14-18), diazacryp tand (22), and diazadithia-crown (23-25) macrocycles has been prepared by treating the appropriate secondary diamine, diazacrown, or dimerca ptan with 2,6-bis[(2 -chloroacetamido)methyl]-4-nitroanisole (BB). Fiv e of these p-nitroanisole-containing macrocycles were reported earlier . Four new bis(p-nitroanisole)-containing macrocycles resulting from a 2 + 2 macrocyclization of diamine or dimercaptan with BE were also is olated. Six of the p-nitroanisole-containing macrocycles (16, 17, 22-2 5) were converted to the p-nitrophenol-containing macrocycles (27-32) on treatment with LiI in refluxing pyridine. Thermodynamic quantities (log K, Delta H, and T Delta S) for the interactions of four new compo unds (24, 27, 31, and 32) with Na+, K+, Ba2+, Ag+, and Pb2+ were evalu ated by calorimetric titration at 25.0 degrees C in either 70% or abso lute methanol solution. The compounds show strong interactions with Ag + and Pb2+ but very weak interactions with Na+, K+, and Ba2+. Ligand 3 1 exhibited high selectivity for Ag+ over Pb2+. X-ray crystal structur es were obtained for diazadithia macrocycle 23 and the Ag+-31 complex.