α- and β-cyclodextrin complexes with n-alkyl carboxylic acids and n-alkyl p-hydroxy benzoates. A molecular mechanics study of 1:1 and 1:2 associations

Antonio C.S. Lino, Yuji Takahata, Carlos Jaime

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17 Citations (Scopus)

Abstract

Molecular mechanics (MM) methods were employed to evaluate stabilization upon formation of inclusion compounds between two different guest molecules and α- and β-cyclodextrins (CDs) for two different stoichiometries 1:1 and 1:2. The two guest molecules studied were n-alkyl carboxylic acids and n-alkyl p-hydroxy benzoates with variety of chain lengths. The computed stability for the inclusion compounds between α-CDs and n-alkyl carboxylic acids reproduced experimental data reported in the literature. The transition between 1:1/1:2 complexes occurred at an alkyl chain length of nC = 9. It was previously demonstrated by diffusion coefficients measures that a stable 1:2 stoichiometry inclusion compound could be formed between n-alkyl p-hydroxy benzoates and α-CD for the chain length nc > 4. The computed results reproduced the experimental ones. The combination between OPLS and GB/SA resulted in better agreements with experiments than those obtained with MM2 and MM3. © 2002 Elsevier Science B.V. All rights reserved.
Original languageEnglish
Pages (from-to)207-213
JournalJournal of Molecular Structure: THEOCHEM
Volume594
Issue number3
DOIs
Publication statusPublished - 18 Oct 2002

Keywords

  • Cyclodextrins
  • Molecular mechanics
  • N-Alkyl carboxylic acids
  • N-Alkyl p-hydroxy benzoates
  • Simulation
  • Stoichiometry

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