Host–Guest Complex of β-Cyclodextrin and Disulfide Form of 4-Aminothiophenol
Source abstract
Abstract
An inclusion complex of β-cyclodextrin and 4-aminothiophenol was assembled by hydrophobic interaction of the host (β-cyclodextrin) and guest (4-aminothiophenol). The complex was isolated as crystalline solid and studied by single crystal X-ray diffraction method along with NMR and IR spectroscopy. Two cyclodextrin rings each containing one disulfide form of 4-aminothiophenol were found to pair up by hydrogen bonding of the outer rim -OH groups. The phenyl disulfide moiety of 4-aminophenyl disulfide molecule was found in the core of β-cyclodextrin, while the amino functional groups were positioned to the exterior of the cyclodextrin ring. Phenyl rings of the guest molecule from each partner of the paired cyclodextrin complex were found parallel to each other, indicating possible π-π stacking interaction between them.
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Research context
OpenAlex topics: Protein purification and stability · Drug Solubulity and Delivery Systems · Innovative Microfluidic and Catalytic Techniques Innovation
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Affiliations
Department of Chemistry, Boswell Science Complex, Tennessee State University, 3500 John A. Merritt Blvd, Nashville, TN 37209, USA
Rigaku Americas Corp., 9009 New Trails Dr., The Woodlands, TX 77381, USA
References (17)
Show source-provided references
1. The crystal structure of the inclusion complex of cyclomaltoheptaose (β-cyclodextrin) with 3,3-dimethylbutylamine10.1016/0008-6215(91)80002-5 ↗
2. Structure of the inclusion complex of β-cyclodextrin with 1,12-dodecanedioic acid using synchrotron radiation data; a detailed dimeric β-cyclodextrin structure10.1107/S0108768199014494 ↗
3. Insulated molecular wires10.1002/anie.200601780 ↗
4. The association of α- and β-cyclodextrins with organic acids10.1021/ja01471a022 ↗
5. Gold nanoparticles dispersed into poly(aminothiophenol) as a novel electrocatalyst-Fabrication of modified electrode and evaluation of electrocatalytic activities for dioxygen reduction10.1016/j.molcata.2006.05.027 ↗
6. A novel mode of inclusion for pyrene in β-cyclodextrin compounds: The crystal structures of β-cyclodextrin with cyclohexanol and pyrene, and with n-octanol and pyrene10.1021/ja972156d ↗
7. Facile synthesis and one-dimensional assembly of cyclodextrin-capped gold nanoparticles and their applications in catalysis and surface-enhanced Raman scattering10.1021/jp903405y ↗
8. Controlled orientation of cyclodextrin derivatives immobilized on gold surfaces10.1021/ja9539812 ↗
9. Reduced fluorescence quenching of cyclodextrin-acetylene dye rotaxanes10.1021/ja0584121 ↗
10. Buston, J.E.H., Young, J.R., and Anderson, H.L. (2000). Rotaxane-encapsulated cyanine dyes: Enhanced fluorescence efficiency and photostability. Chem. Commun., 905–906.10.1039/b001812k ↗
11. Light stability of a β-cyclodextrin inclusion complex of a cyanine dye10.1039/FT9949003517 ↗
12. Buston, J.E.H., Marken, F., and Anderson, H.L. (2001). Enhanced chemical reversibility of redox processes in cyanine dye rotaxanes. Chem. Commun., 1046–1047.10.1039/b102068o ↗
13. Stanier, C.A., O’Connell, M.J., Clegg, W., and Anderson, H.L. (2001). Synthesis of fluorescent stilbene and tolan rotaxanes by Suzuki coupling. Chem. Commun., 493–494.10.1039/b010015n ↗
14. Terao, J., Tang, A., Michels, J.J., Krivokapic, A., and Anderson, H.L. (2004). Synthesis of poly(para-phenylenevinylene) rotaxanes by aqueous Suzuki coupling. Chem. Commun., 56–57.10.1039/b311762f ↗
15. Cyclodextrin-threaded conjugated polyrotaxanes as insulated molecular wires with reduced interstrand interactions10.1038/nmat750 ↗
16. Cholesterol recognition and binding by cyclodextrin dimers10.1021/ja961567b ↗
17. Sinusoidal ribbon waves in the crystal structure of bis(4-aminophenyl) disulfide10.1016/S0025-5408(98)00089-0 ↗