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http://dx.doi.org/10.5012/jkcs.2009.53.6.640

mPW1PW91 Calculated Conformational Study of Calix[n]arene (n = 4,5,6): Hydrogen Bond  

Kim, Kwang-Ho (Department of Chemistry, Chung-Ang University)
Choe, Jong-In (Department of Chemistry, Chung-Ang University)
Publication Information
Journal of the Korean Chemical Society / v.53, no.6, 2009 , pp. 640-652 More about this Journal
Abstract
We have performed mPW1PW91 calculations to investigate the conformational characteristics and hydrogen bonds of p-tert-butylcalix[4]arene (1), p-tert-butylcalix[5]arene (2), calix[6]arene (3) and p-tertbutylcalix[6]arene (4). The structures of the different conformers of 1-3 were optimized by using mPW1PW91/6-31+G(d,p) method. The relative stability of the four conformers of 1 is in the following order: cone (most stable) > partial-cone > 1,2-alternate > 1,3-alternate. The relative stability of the conformers of 2 is in the following order: cone (most stable) > 1,2-alternate > partial-cone > 1,3-alternate. The relative stability of the various conformers of 3 is in the following order: cone (pinched: most stable) > partial-cone > cone (winged) - 1,2-alternate - 1,2,3-alternate > 1,4-alternate > 1,3-alternate > 1,3,5-alternate. The structures of the various conformers of 4 were optimized by using the mPW1PW91/6-31G(d,p) method followed by single point calculation of mPW1PW91/6-31+G(d,p). The relative stability of the conformers of 4 is in the following order: cone (pinched) > 1,2-alternate > cone (winged) > 1,4-alternate - partial-cone > 1,2,3-alternate > 1,3,5-alternate > 1,3-alternate. The primary factor affecting the relative stabilities of the various conformers of the 1-4 are the number and strength of the intramolecular hydrogen bonds. The hydrogen-bond distances are discussed based on two different calculation methods (B3LYP and mPW1PW91).
Keywords
Calix[n]arene; Conformer; mPW1PW91/6-31+G; Hydrogen bond;
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