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Titolo:
Synthesis and ion selectivity of tetrakis[(N,N-dialkylaminocarbonyl) methoxy]homocalix[4]arenes
Autore:
Yamato, T; Iwasa, T; Zhang, FL;
Indirizzi:
Saga Univ, Fac Sci & Engn, Dept Appl Chem, Saga 8408502, Japan Saga Univ Saga Japan 8408502 & Engn, Dept Appl Chem, Saga 8408502, Japan
Titolo Testata:
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY
fascicolo: 3-4, volume: 39, anno: 2001,
pagine: 285 - 294
SICI:
1388-3127(200104)39:3-4<285:SAISOT>2.0.ZU;2-Y
Fonte:
ISI
Lingua:
ENG
Soggetto:
X-RAY CRYSTAL; SPHERAND-TYPE CALIXARENES; CONFORMATIONAL ISOMERS; MACROCYCLIC METACYCLOPHANES; MOLECULAR INCLUSION; CHIRAL SUBSTITUENTS; CATION COMPLEXATION; BINDING PROPERTIES; ALKALI CATIONS; REGIO-ISOMERS;
Keywords:
macrocycles; homocalixarenes; O-alkylation; template effect; conformations; metal cation complexation; ionophores;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
71
Recensione:
Indirizzi per estratti:
Indirizzo: Yamato, T Saga Univ, Fac Sci & Engn, Dept Appl Chem, Honjo Machi 1, Saga 8408502, Japan Saga Univ Honjo Machi 1 Saga Japan 8408502 Saga 8408502, Japan
Citazione:
T. Yamato et al., "Synthesis and ion selectivity of tetrakis[(N,N-dialkylaminocarbonyl) methoxy]homocalix[4]arenes", J INCL P MA, 39(3-4), 2001, pp. 285-294

Abstract

An attempted O-alkylation of the flexible macrocycle 1 with N,N-dialkylchloroacetamides in the presence of NaH, K2CO3 or Cs2CO3 gave only one pure stereoisomer 1,4-alternate-2a-c, while other possible isomers were not observed. In contrast, only an intractable mixture was obtained when Na2CO3 was used as base. The structural characterization of these products is discussed. The two-phase solvent extraction data indicated that tetrakis(N,N-dialkylaminocarbonyl) derivatives 2b-c show strong alkali metal cation affinity and the extractabilities are much higher than that for the corresponding calix[4]arene tetraethyl ester 4 and homocalix[4]arene tetraethyl ester 3. HighLi+ and Na+ extractabilities were observed for tetrakis[(N,N-diethylaminocarbonyl) derivative 2b. However, no significant high ion selectivity for alkali metal cations was observed in tetraamide 2b. H-1-NMR titration of tetraamide 2b with KSCN clearly demonstrates that a 1:1 complex is formed with retention of the original symmetry to be conformationally frozen on the NMRtime scale.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 02/04/20 alle ore 10:43:50