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Related Concept Videos

Carbocations02:10

Carbocations

Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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Cationic Chain-Growth Polymerization: Mechanism

The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the generated carbocation,...
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In complexation reactions, metal atoms or cations interact with ligands to form donor-acceptor adducts called metal complexes. Ligands that bind through one donor site are monodentate, ligands with two donor sites are bidentate, and those with more than two donor sites are polydentate ligands. For example, ethylene diamine is a bidentate ligand that binds through two nitrogen donor atoms, forming a five-membered ring. EDTA is a polydentate ligand that binds through four oxygen and two nitrogen...
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Updated: Jun 25, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Published on: April 19, 2019

Complexation of alpha-cyclodextrin with carborane derivatives in aqueous solution.

Kiminori Ohta1, Shunsuke Konno, Yasuyuki Endo

  • 1Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, Aoba-ku, Senhai 981-8558, Japan.

Chemical & Pharmaceutical Bulletin
|March 3, 2009
PubMed
Summary

This study reveals carborane derivatives can complex with alpha-cyclodextrin (alpha-CD) in water for the first time. Complexation is weaker with alpha-CD than beta-CD due to cavity size and orientation effects.

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Area of Science:

  • Supramolecular Chemistry
  • Host-Guest Chemistry
  • Carborane Chemistry

Background:

  • Complexation of carborane derivatives with beta-cyclodextrin (beta-CD) is established.
  • Alpha-cyclodextrin (alpha-CD) is a macrocyclic host with a smaller hydrophobic cavity compared to beta-CD.
  • Understanding host-guest interactions is crucial for designing novel molecular systems.

Purpose of the Study:

  • To investigate the complexation of carborane derivatives with alpha-cyclodextrin in aqueous solution.
  • To determine the stoichiometry and association constants of these novel complexes.
  • To compare the complexation ability of alpha-CD with that of beta-CD for carborane derivatives.

Main Methods:

  • Job's plots were employed to determine the stoichiometry of the carborane:alpha-CD complexes.
  • Nuclear Magnetic Resonance (NMR) titration studies were utilized to estimate the association constants (K(a)).
  • Comparative analysis with existing beta-CD complexation data was performed.

Main Results:

  • The first observation of carborane derivative complexation with alpha-CD in aqueous solution is reported.
  • All carborane derivatives formed 1:1 complexes with alpha-CD.
  • Complexation ability and selectivity for alpha-CD were significantly lower than for beta-CD.
  • The smaller cavity of alpha-CD likely limits the accommodation of the carborane cage, resulting in weaker interactions.
  • Hydrogen bonding between carborane C-H/substituents and alpha-CD rim alcohols may contribute to binding.
  • Ortho- and meta-carborane derivatives exhibited slightly stronger association constants than para-isomers.

Conclusions:

  • Carborane derivatives can form 1:1 inclusion complexes with alpha-cyclodextrin, albeit with reduced affinity compared to beta-cyclodextrin.
  • The size of the cyclodextrin cavity plays a critical role in the strength of carborane complexation.
  • Carborane orientation and potential hydrogen bonding influence the binding thermodynamics, offering insights for molecular recognition design.