Related Experiment Video
Updated: Jul 16, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Hydrogen-bonded dimers of tetra-urea calix[4]arenes stable in THF
Ivan Vatsouro1, Valentyn Rudzevich, Volker Böhmer
1Abteilung Lehramt Chemie, Fachbereich Chemie, Pharmazie und Geowissenschaften, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, D-55099 Mainz, Germany.
Abstract:
[structure: see text]. Whereas tetra-urea derivatives of tetra-alkoxy calix[4]arenes 1 exist as single molecules in THF, dimeric hydrogen-bonded capsules are exclusively found for the corresponding calix[4]arene derivatives 3 and 2 with two or four free hydroxyl groups. Comparison with the rigidified tetra-urea 5 suggests that this increased stability of the dimers is due to the stabilization of their four-fold symmetry by intramolecular hydrogen bonds between the phenolic hydroxyl groups.
Related Concept Videos
Stability of Conjugated Dienes
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
π Molecular Orbitals of 1,3-Butadiene
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
Hydrogen Bonds
Hydrogen Bonds
Stability of Substituted Cyclohexanes
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...
¹H NMR of Labile Protons: Deuterium (²H) Substitution

