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http://dx.doi.org/10.5012/bkcs.2010.31.11.3247

BLYP and mPW1PW91 Calculated Structures and IR Spectra of the Stereoisomers of Tetra-O-methylsulfinylcalix[4]arene

Choe, Jong-In (Department of Chemistry, Chung-Ang University)

Publication Information

Bulletin of the Korean Chemical Society / v.31, no.11, 2010 , pp. 3247-3251 More about this Journal

Abstract

Molecular structures of the various conformers for the four stereoisomers of tetra-t-butyl-tetra-O-methylsulfinylcalix[4]arene (1) were optimized using DFT BLYP and mPW1PW91/6-31G(d,p) (hybrid HF-DF) calculation methods. We have analyzed the total electronic and Gibbs free energies and normal vibrational frequencies of 16 different structures from four major conformations (cone (CONE), partial cone (PC), 1,2-alternate (1,2-A), 1,3-alternate (1,3-A)) of the four stereoisomers [1(rccc), 1(rcct), 1(rctt), 1(rtct)]. The mPW1PW91/6-31G(d,p) calculations suggested that the $1(rccc)_{CONE}$ , $1(rcct)_{PC}$ , $1(rctt)_{PC}$ , and $1(rtct)_{1,3-A}$ were the most stable conformations of the respective stereoisomers. These outcomes are in accordance with the experimental structures obtained from X-ray crystallography. The electrostatic repulsion between the sulfinyl and methoxy groups is a primary factor for the relative stabilities of the four different conformations. The IR spectra of the most stable conformers [ $1(rccc)_{CONE}$ , $1(rcct)_{PC}$ , $1(rctt)_{PC}$ , $1(rtct)_{1,3-A}$ ] of each stereoisomer were compared to each other.

Keywords

mPW1PW91; Conformer; Stereoisomer; Infrared; Sulfinylcalix[4]arene;

Citations & Related Records

Times Cited By KSCI : 1 (Citation Analysis)
Times Cited By Web Of Science : 1 (Related Records In Web of Science)
Times Cited By SCOPUS : 1

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