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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 21, Number 11
BKCSDE 21(11)
November 20, 2000 

Synthesis of Diaza-18-Crown-6-Functionalized β-Cyclodextrin Derivatives at the Secondary Side and Induced Circular Dichroism Studies of Their Complexes with (2-Naphthoxy)alkylammonium Ions
Kwanghee Koh Park, Young Sin Kim, Hee Kyoung Jung, Hee Eun Song, Joon Woo Park
β-Cyclodextrin derivatives connected with diaza-18-crown-6 through flexible bridges (R) at the secondary face 1a-c (1a: R = -(CH₂)4-; 1b: R = -CH₂CH₂OCH₂CH2-; 1c: R = -(CH₂)8-) have been prepared. The association constants of 1 with (2-naphthoxy)alkylammonium ions (2a: alkyl = butyl; 2b: alkyl = octyl) were determined by induced circular dichroism (ICD) spectroscopy and it was found that the derivatization of β-CD with the diazacrown resulted in enhanced binding with 2, compared to the native β-CD. ICD Characteristics of the host-guest complexes indicate that a part of the alkylammonium moiety of 2 is protruded from the secondary side of the β-CD cavity, and the guest molecules 2a and 2b move to the secondary and primary side, respectively, to make the binding of the ammonium group with the diaza-18-crown-6 moiety more feasible. The energy accompanied by the relocation of the guest molecules inside β-CD moiety is compensated by the interaction energy between the ammonium ion and diazacrown ether.
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