Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

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 with both...
Crystal Field Theory - Tetrahedral and Square Planar Complexes02:46

Crystal Field Theory - Tetrahedral and Square Planar Complexes

Tetrahedral Complexes
Crystal field theory (CFT) is applicable to molecules in geometries other than octahedral. In octahedral complexes, the lobes of the dx2−y2 and dz2 orbitals point directly at the ligands. For tetrahedral complexes, the d orbitals remain in place, but with only four ligands located between the axes. None of the orbitals points directly at the tetrahedral ligands. However, the dx2−y2 and dz2 orbitals (along the Cartesian axes) overlap with the ligands less than the dxy,...
¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR01:15

¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR

The axial and equatorial protons in cyclohexane can be distinguished by performing a variable-temperature NMR experiment. In this process, except for one proton, the remaining eleven protons are replaced by deuterium. The deuterium substitution avoids the possible peak splitting caused by the spin-spin coupling between the adjacent protons. The remaining proton flips between the axial and equatorial positions.
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal tetrahedral value,...
Chair Conformation of Cyclohexane02:02

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 staggered...
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that was based on the...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Design, synthesis, and anticancer activity of novel isocryptolepine 'aza' type acyl thiourea derivatives via combined experimental and computational approach.

Bioscience reports·2025
Same author

A novel aurone RNA CAG binder inhibits the huntingtin RNA-protein interaction.

RSC medicinal chemistry·2024
Same author

Adjusting the Number of Functional Groups in Vicinal Bis(trichlorosilylated) Benzenes.

Chemistry (Weinheim an der Bergstrasse, Germany)·2024
Same author

Borylation and rearrangement reactions of azasilaanthracenes to afford B,N-doped nanographenes.

Dalton transactions (Cambridge, England : 2003)·2024
Same author

Tetramerization of BEB-Doped Phenalenyls to Obtain (BE)<sub>8</sub>-[16]Annulenes (E = N, O).

Journal of the American Chemical Society·2024
Same author

Combination of Betulinic Acid Fragments and Carbonic Anhydrase Inhibitors-A New Drug Targeting Approach.

Pharmaceutics·2024

Related Experiment Video

Updated: Jun 30, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Cyclic tetraureas with variable flexibility--synthesis, crystal structures and properties.

Denys Meshcheryakov1, Françoise Arnaud-Neu, Volker Böhmer

  • 1Fachbereich Chemie, Pharmazie und Geowissenschaften, Abteilung Lehramt Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, D-55099, Mainz, Germany.

Organic & Biomolecular Chemistry
|September 20, 2008
PubMed
Summary

New macrocyclic tetraurea molecules were synthesized and tested as anion receptors. The XXXD macrocycle showed the strongest binding affinity for acetate anions, demonstrating potential for selective anion recognition.

More Related Videos

Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level
06:55

Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level

Published on: September 26, 2016

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
12:30

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

Related Experiment Videos

Last Updated: Jun 30, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level
06:55

Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level

Published on: September 26, 2016

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
12:30

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Host-Guest Chemistry

Background:

  • Macrocyclic molecules with amide or urea functionalities are recognized for their potential as anion receptors.
  • The design and synthesis of novel macrocyclic structures are crucial for advancing anion binding technologies.

Purpose of the Study:

  • To synthesize a series of 32-membered macrocycles incorporating xanthene (X) and/or diphenyl ether (D) units linked by urea groups.
  • To investigate the conformational properties, hydrogen-bonding patterns, and anion binding capabilities of these novel macrocyclic tetraureas.

Main Methods:

  • Synthesis of six macrocyclic tetraurea combinations (XXXX, XXXD, XXDD, XDXD, XDDD, DDDD).
  • Single-crystal X-ray analysis for structural characterization of selected compounds.
  • Anion interaction studies using (1)H NMR spectroscopy.
  • Determination of stability constants via UV spectroscopy.
  • Molecular dynamics (MD) simulations to probe conformational behavior and solvation effects.

Main Results:

  • Two macrocyclic structures (DDDD and XXXD) were confirmed by X-ray crystallography, revealing distinct conformations and hydrogen-bonding patterns.
  • No direct intermolecular hydrogen bonds were observed between macrocyclic tetraurea molecules.
  • Stability constants varied significantly, with the XXXD macrocycle exhibiting the strongest binding to acetate (log beta = 7.4 ± 0.2).
  • MD simulations indicated similar conformations for most molecules, with specific solvation shells suggesting preorganization for certain anion types.

Conclusions:

  • The synthesized macrocyclic tetraureas demonstrate tunable anion binding affinities based on their structural composition.
  • The XXXD macrocycle shows promising selectivity for acetate anions, highlighting its potential in anion recognition applications.
  • Conformational flexibility and solvation effects play critical roles in the preorganization and binding of anions by these macrocyclic receptors.