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http://dx.doi.org/10.5012/bkcs.2014.35.5.1323

mPW1PW91 Calculated Structures and IR Spectra of the Conformational Stereoisomers of C-Cyanophenyl Pyrogallol[4]arene  

Ahn, Sangdoo (Department of Chemistry, Chung-Ang University)
Park, Tae Jung (Department of Chemistry, Chung-Ang University)
Choe, Jong-In (Department of Chemistry, Chung-Ang University)
Publication Information
Bulletin of the Korean Chemical Society / v.35, no.5, 2014 , pp. 1323-1328 More about this Journal
Abstract
Molecular structures of the various conformational stereoisomers of 2,8,14,20-cyanophenyl pyrogallol[4]arenes 1 were optimized using the mPW1PW91 (hybrid Hartree-Fock density functional) calculation method. The total electronic and Gibbs free energies and the normal vibrational frequencies of the different structures from three major conformations (CHAIR, TABLE, and 1,2-Alternate) of the four stereoisomers [1(rccc), 1(rcct), 1(rctt), and 1(rtct)] were analyzed. The mPW1PW91/6-31G(d,p) calculations suggested that $1(rcct)_{1,2-A}$, 1(rctt)CHAIR, and $1(rtct)_{CHAIR}$ were the more stable conformations of the respective stereoisomers. Hydrogen bonding is the primary factor for the relative stabilities of the various conformational isomers, and maximizing the ${\pi}-{\pi}$ interaction between the cyanophenyl rings is the secondary factor. The calculated IR spectra of the more stable conformers [$1(rctt)_{CHAIR}$, $1(rcct)_{1,2-A}$, $1(rtct)_{CHAIR}$] were compared with the experimental IR spectrum of $1(rtct)_{CHAIR}$.
Keywords
mPW1PW91; Conformer; Stereoisomer; IR spectrum; Cyanophenyl pyrogallol[4]arene;
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