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

최종인|김광호
대한화학회|2009.12|대한화학회지 (Journal of the Korean Chemical Society)|제53권 제6호|pp. 640-652

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참고문헌

키워드

양자역학Hydrogen bond수소결합mPW1PW91Conformer이형체Calix[n]arenemPW1PW91/6-31+G캘릭스[n]아렌
주제분류화학

초록

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).

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).

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