Complexes of primary alkylammonium salts and secondary dialkylammonium salts with diazaparacyclophanes

Cation complexing properties of synthetic macrocyclic polyether-diester ligands containing the pyridine subcyclic unit

“…A similar kinetic stability order for the complexation of aryldiazonium salts by compounds 8-10 was observed by Bartsch and co-workers25 and investigated by Izatt et al26 The data in Table III also shows that the 18-membered ring compounds (2, 6, and 7) form more stable complexes than the compounds with 21-membered rings (8)(9)(10). Complexes were formed between primary alkylammonium ions and the larger ring compounds (11)(12)(13)(14)(15) but the AG*C values must be less than 8 kcal/mol since a separation of the NMR signals was not observed at -100 °C. The data for the complexation of benzylammonium perchlorate with a sulfur-containing pyridino polyether diester compound (18) are also included in Table III.…”

“…The low-temperature peak separations were 136-260 Hz for the 18-membered rings and 43-64 Hz for the 21 -membered rings. The complexes for the larger compounds (11)(12)(13)(14) formed Calculation of kinetic parameters for the formation of the complexes was done using eq l22 and 2: kc = /2…”

Synthesis of aza-crown ethers

“…OTs, Br Stoddart and co-workers used a similar reaction sequence to prepare a 1,4-benzodiaza-crown ether (method BA). 195 Using bis(phthalimide) derivatives of the oligoethylene glycols, Komalow and co-workers prepared crown ethers containing a phthalamide moiety (method BB). 196,197 The starting bis(phthalimide) and diamine were reacted in a water-methanol mixture, and the product was isolated by chromatography.…”