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http://dx.doi.org/10.5012/bkcs.2006.27.11.1737

DFT Study of Bis(Crown-Ether) Analogue of Troger’s Base Complexed with Bisammonium Ions: Hydrogen Bonds  

Kim, Kwan-Ho (Department of Chemistry, Chung-Ang University)
Choe, Jong-In (Department of Chemistry, Chung-Ang University)
Publication Information
Bulletin of the Korean Chemical Society / v.27, no.11, 2006 , pp. 1737-1740 More about this Journal
Abstract
The optimized structures and complexation energies of bis(18-crown-6-ether) analogue (2) of Trgers 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 [$-(CH_2)_{n-}$, 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 ([$NH_3(CH_2)_nNH_3$] $Cl_2$).
Keywords
DFT B3LYP/6-31G(d,p); Bis(crown-ether); Bisammonium ion; Complex;
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