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Titolo:
FERROCENE-APPENDED CYCLODEXTRINS - THE EFFECTS OF TEMPERATURE, ORGANIC-SOLVENT, LENGTH OF SPACER, AND CAVITY SIZE ON THE COMPLEXATION BEHAVIOR
Autore:
SUZUKI I; CHEN QA; UENO A; OSA T;
Indirizzi:
TOHOKU UNIV,INST PHARMACEUT,AOBA KU SENDAI MIYAGI 980 JAPAN TOHOKU UNIV,INST PHARMACEUT,AOBA KU SENDAI MIYAGI 980 JAPAN TOKYO INST TECHNOL,FAC BIOSCI & BIOTECHNOL,DEPT BIOENGN,MIDORI KU YOKOHAMA KANAGAWA 227 JAPAN
Titolo Testata:
Bulletin of the Chemical Society of Japan
fascicolo: 5, volume: 66, anno: 1993,
pagine: 1472 - 1481
SICI:
0009-2673(1993)66:5<1472:FC-TEO>2.0.ZU;2-H
Fonte:
ISI
Lingua:
ENG
Soggetto:
INDUCED CIRCULAR-DICHROISM; ADAMANTANECARBOXYLATE INCLUSION COMPLEXES; HOST-GUEST COMPLEXATION; ONE-ELECTRON TRANSFER; BETA-CYCLODEXTRIN; GAMMA-CYCLODEXTRIN; FERROCENECARBOXYLIC ACID; ALPHA-CYCLODEXTRIN; BINDING ABILITY; ELECTROCATALYTIC OXIDATION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
53
Recensione:
Indirizzi per estratti:
Citazione:
I. Suzuki et al., "FERROCENE-APPENDED CYCLODEXTRINS - THE EFFECTS OF TEMPERATURE, ORGANIC-SOLVENT, LENGTH OF SPACER, AND CAVITY SIZE ON THE COMPLEXATION BEHAVIOR", Bulletin of the Chemical Society of Japan, 66(5), 1993, pp. 1472-1481

Abstract

Inclusion phenomena of cyclodextrins (CyDs) bearing a ferrocene moiety, 1-4, which have different cavity sizes and spacer lengths, were investigated by circular dichroism (CD) spectroscopy in pure ethylene glycol (EG) and 20% EG aqueous solution. Beta-CyD derivatives, 1 and 3, and a gamma-CyD derivative, 4, form intramolecular complexes, includingthe ferrocene moiety in the CyD cavity with orientation similar to that in corresponding native CyD-ferrocene complexes, while another gamma-CyD derivative, 2, which has no spacer alkyl chain, takes various conformations. The host-guest binding constants of 1-4 for several guests revealed that the ferrocene moiety of 1-4 depresses the guest binding, acting as an intramolecular inhibitor in guest binding. In particular, the depression was remarkable for 3 and 4 and the spacer alkyl chain was suggested to stabilize the intramolecular complexes. The ferrocene modified CyDs exhibit similar trends in guest selectivity to thoseof native CyDs. The effects of EG content on the binding constants of1 and 2 revealed that hydrophobic effect operated in the guest accommodation. Thermodynamic parameters for the binding processes of 1 and 2for 1-adamantanol were obtained from the temperature variations in binding constants, the values being -21.9 kJ mol-1 for DELTAH-degrees and 2.76 J mol-1 K-1 for DELTAS-degrees for 1 and -25.1 kJ mol-1 for DELTAH-degrees and -36.1 J mol-1 K-1 for DELTAS-degrees for 2. These values indicated that the complexation of 1 and 2 for 1-adamantanol was governed both by hydrophobic effect and van der Waals interaction, and the latter was especially important in the case of 1 and 1-adamantanol.

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Documento generato il 29/11/20 alle ore 17:46:26