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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 27, Number 11
BKCSDE 27(11)
November 20, 2006 

DFT Study of Bis(Crown-Ether) Analogue of Troger’s Base Complexed with Bisammonium Ions: Hydrogen Bonds
Kwangho Kim, Jong-In Choe*
DFT B3LYP/6-31G(d,p), Bis(crown-ether), Bisammonium ion, Complex
The optimized structures and complexation energies of bis(18-crown-6-ether) analogue (2) of Troger’s base (1) with a series of primary alkylbisammonium ions have been calculated by DFT B3LYP/6-31G(d,p) method. The calculated complexation efficiency (-142.84 kcal/mol) of 2 for butane-1,4-diylbisammonium guest is better than twice of the value (-61.40 kcal/mol) for butylammonium ion. The multiple hydrogen-bond abilities for the complexes are described as the function of the length of the alkyl substituents of the bisammonium guests with normal-alkyl chain [-(CH2)n-, n = 4-8]. The longer bisammonium guest shows the stronger hydrogen-bonding characterizations (the distance and the quasi-linear angle of the N-H…O) to the host 2 than the shorter bisammonium ions. These calculated results agree with the experimental data of the complexation of 2 with bisammonium salts ([NH3(CH2)nNH3] Cl2).
1737 - 1740
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