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Journal of Solution Chemistry

, Volume 35, Issue 10, pp 1377–1388 | Cite as

Experimental and Molecular Mechanical Studies of Complexation of Some 2H- and 3H- Indole Derivatives with Aqueous β-Cyclodextrin

  • Khaldoun A. Al-Sou’od
  • Mohammad B. Zughul
  • Adnan A. Badwan
Original Paper

Abstract

Phase solubility diagrams (PSDs) at 25 C and molecular mechanical (MM) modeling were used to study the aqueous complexation of some 2H- and 3H-indole derivatives with β-cyclodextrin (β-CD). Among the 3H-indole derivatives investigated in this work, indole-3H-butyric acid forms the most stable 1:1 complex of the B s -type PSD, whereas shorter chain derivatives form soluble 1:1 complexes (A L -type PSDs) with their stability increasing as the chain length increases. Indole-2 carboxylic acid forms highly stable 1:1 and 1:2 complexes, with the lower-order complex reaching saturation first (B s -type PSD). MM modeling indicates that the stability of the complex is highly correlated with the flexibility of the 3H-indole hydrocarbon chain, which yields a better geometrical fit within the β-CD cavity resulting from different hydrophilic interactions. These interactions are represented in the H-bonding of the carboxyl group with the primary hydroxyl group network that is situated at the narrow rim of the cavity, and also by a favorable interaction of the aromatic ring with the hydroxyl group network at the other rim.

Keywords

Indole β-Cyclodextrin Inclusion compounds Molecular mechanics Phase-solubility diagrams 

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Notes

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Copyright information

© Springer Science + Business Media, Inc. 2006

Authors and Affiliations

  • Khaldoun A. Al-Sou’od
    • 1
  • Mohammad B. Zughul
    • 2
  • Adnan A. Badwan
    • 3
  1. 1.Department of ChemistryAl al-Bayt UniversityMafrakJordan
  2. 2.Department of ChemistryUniversity of JordanAmmanJordan
  3. 3.The Jordanian Pharmaceutical Manufacturing CompanyNaorJordan

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