Monatshefte für Chemie / Chemical Monthly

, Volume 131, Issue 8, pp 849-855

A Systematic Quantum Chemistry Study on Cyclodextrins

  • Xiao-Song LiAffiliated with Department of Chemistry, University of Science and Technology of China, Hefei 230026, China
  • , Lei LiuAffiliated with Department of Chemistry, Columbia University, New York, NY 10027, USA
  • , Ting-Wei MuAffiliated with Department of Chemistry, University of Science and Technology of China, Hefei 230026, China
  • , Qing-Xiang GuoAffiliated with Department of Chemistry, University of Science and Technology of China, Hefei 230026, China

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Summary.

 AM1 and PM3 modeling of β-hydroxyethyl ether and α-(1→4)-glucobiose indicated that PM3 is advantageous to AM1 in cyclodextrin (CD) chemistry. The conclusion was supported by direct structure optimization of α- and β-CD with AM1 and PM3, in which AM1 gave badly distorted geometries due to unreasonable hydrogen bonding, whereas PM3 reproduced the crystalline structures rather well. Ab initio calculation was for the first time performed on CD, demonstrating the feasibility of this method for future studies concerning CD chemistry. The results also provided valuable insights into the driving forces in CD molecular recognition.

Keywords. Ab initio calculations; Cyclodextrins; Density functional calculations; Molecular modeling; Semiempirical calculations.