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Cycloalkanes

Cycloalkanes

Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...

Aromatic Hydrocarbon Cations: Structural Overview

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...

Fruit Development, Structure, and Function

Fruit Development, Structure, and Function

Fruits form from a mature flower ovary. As seeds develop from the ovules contained within, the ovary wall undergoes a series of complex changes to form fruit. In some fruits, such as soybeans, the ovary wall dries; in other fruits, such as grapes, it remains fleshy. In some cases, organs other than the ovary contribute to fruit formation; such fruits are called accessory fruits.

Chair Conformation of Cyclohexane

Chair Conformation of Cyclohexane

The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this...

Cycloaddition Reactions: Overview

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.

Disubstituted Cyclohexanes: cis-trans Isomerism

Disubstituted Cyclohexanes: cis-trans Isomerism

Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....

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Acyclic cucurbit[n]uril bearing alkyl sulfate ionic groups.

Christian Akakpo¹, Peter Y Zavalij¹, Lyle Isaacs¹

¹Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, United States.

Beilstein Journal of Organic Chemistry

|April 8, 2025

Summary

A new acyclic cucurbituril host, C1, with alkyl sulfate groups shows lower water solubility and self-association than M1. C1 exhibits enhanced binding to ammonium guests, particularly quaternary ones.

Keywords:

X-ray crystallography cucurbituril host–guest chemistry isothermal titration calorimetry molecular container

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Area of Science:

Supramolecular Chemistry
Host-Guest Chemistry
Organic Synthesis

Background:

Acyclic cucurbit[n]urils (CB[n]) are macrocyclic hosts with tunable properties.
Ionic functional groups significantly influence CB[n] solubility and binding.
Understanding structure-property relationships is key for designing novel CB[n] hosts.

Purpose of the Study:

To synthesize and characterize a novel acyclic cucurbit[n]uril host (C1) bearing four alkyl sulfate ionic groups.
To investigate the impact of alkyl sulfate groups on C1's solubility, self-association, and molecular recognition properties.
To compare the binding affinities of C1 with a related sulfonate-functionalized host (M1) for ammonium guests.

Main Methods:

Synthesis and characterization of the acyclic cucurbit[n]uril host C1.
X-ray crystallography to determine the structure of the C1·Me-CHDA complex.
1H NMR spectroscopy and dilution experiments to assess solubility and self-association.
1H NMR spectroscopy and isothermal titration calorimetry (ITC) to evaluate host-guest binding.

Main Results:

The acyclic cucurbit[n]uril host C1 was successfully synthesized and characterized.
X-ray crystal structure of the C1·Me-CHDA complex was determined.
C1 exhibited significantly lower water solubility (4 mM) compared to M1 (346 mM) and minimal self-association.
C1 demonstrated slightly stronger binding affinities than M1 for ammonium guests, with a preference for quaternary ammonium ions.

Conclusions:

The presence of alkyl sulfate groups in acyclic cucurbit[n]urils influences their physicochemical properties, notably reducing water solubility.
Acyclic cucurbituril host C1 displays distinct molecular recognition behavior compared to its sulfonate analog M1.
C1 shows potential as a host molecule for specific ammonium guests, particularly quaternary ammonium ions.