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Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

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This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
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Substituent Effects on Acidity of Carboxylic Acids01:31

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The acidity of carboxylic acids is influenced by the nature of the substituents bounded to the functional group. The acid strength is determined by the stability of the carboxylate anion—the conjugate base formed by dissociating the corresponding carboxylic acid.
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Complexation Equilibria: Factors Influencing Stability of Complexes01:09

Complexation Equilibria: Factors Influencing Stability of Complexes

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In complexation reactions, metal cations are the electron pair acceptors, and the ligands are the electron pair donors. The stability of the metal complexes depends primarily on the complexing ability of the central metal ion and the nature of the ligands. Generally, the complexing ability of the metal ion depends on the size and charge of the ion. As the metal ion size increases, the stability of the metal complexes decreases, provided that the valency of the metal ion and the ligands remain...
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Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

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Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.
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Reactions of Carboxylic Acids: Introduction01:41

Reactions of Carboxylic Acids: Introduction

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Carboxylic acids possess an acidic –COOH functional group. The acidity can be attributed to the resonance stabilization of their conjugate base, wherein the negative charge is delocalized over both oxygen atoms.
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Types of Enols and Enolates01:19

Types of Enols and Enolates

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Aldehydes and ketones form enols, although only about 1% of the enol is present at the equilibrium for simple monocarbonyl compounds. The enol form is undetectable for acetaldehyde, present as only 1.5 × 10−4 % of acetone, and present as only 1.2% of cyclohexanone. Two kinds of regioisomeric enols are possible for unsymmetrical ketones, and their net composition is 1% at equilibrium. This instability is due to the lower bond energy of C=C than the C=O group. The additional...
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Controlling the Size, Shape and Stability of Supramolecular Polymers in Water
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Certain carboxylic acid buffers can destabilize β-cyclodextrin complexes by competitive interaction.

Lisa Samuelsen1, René Holm2, Christian Schönbeck

  • 1Department of Science and Environment, Roskilde University, Universitetsvej 1, DK-4000 Roskilde, Denmark.

International Journal of Pharmaceutics
|September 11, 2020
PubMed
Summary

Buffer choice significantly impacts adamantanol binding to cyclodextrins. Carboxylic acid buffers, especially those with longer carbon chains and hydroxyl groups, reduce binding affinity and can compete with guest molecules. Careful buffer selection is crucial for cyclodextrin research.

Keywords:
Binding constantDrug formulationEquilibrium constantHost-guest chemistryHydrophobic interactionIonization

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Area of Science:

  • Supramolecular Chemistry
  • Analytical Chemistry

Background:

  • Cyclodextrins (CDs) are widely used in drug delivery and separation science.
  • Understanding buffer effects on CD complexation is vital for optimizing applications.

Purpose of the Study:

  • To investigate the influence of thirteen different buffers on adamantanol binding to beta-cyclodextrin (β-CD) and hydroxypropyl-β-cyclodextrin (HP-β-CD).
  • To elucidate the binding mechanisms and structural factors governing buffer-CD interactions.

Main Methods:

  • Spectrophotometric determination of stability constants and binding enthalpies.
  • Nuclear Magnetic Resonance (NMR) spectroscopy (¹H and ROESY) to study inclusion complex formation.

Main Results:

  • Stability constants for β-CD-adamantanol complexes varied from 14,800 to 46,000 M⁻¹.
  • Seven carboxylic acid buffers significantly reduced adamantanol binding via competitive mechanisms.
  • Buffer-CD binding constants ranged from 4 to 44 M⁻¹, influenced by buffer structure (carbon chain length, hydroxyl groups).
  • NMR confirmed citric acid inclusion in β-CD, with ambiguous results for succinic and maleic acids.

Conclusions:

  • Certain buffers, particularly carboxylic acids, can interfere with CD-guest complexation.
  • Buffer structure dictates its interaction strength with CDs.
  • Careful buffer selection is essential for reliable CD-based research and applications.