Related Experiment Video
Updated: Aug 12, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
3,6,9,16,19,22-Hexaazatricyclo
1School of Chemistry, University of St Andrews, Fife, Scotland. cg@st-andrews.ac.uk
Abstract:
The adduct (1) formed between the hexaaza macrocycle 3,6,9,16,19,22-hexaazatricyclo[22.2.2.2(11,14]triconta-1(26),11(29),12,14(30),24,27-hexaene, C24H38N6, and 4,4'-sulfonyldiphenol, O2S(C6H4OH)2, is a salt [(C24H40N6)2+].2[(HOC6H4SO2C6H4O)-], and the adduct (2) formed by the same macrocyclic amine with 4,4'-biphenol is an aquated salt which also contains neutral biphenol molecules, [(C24H40N6)2+]. 2[(HOC6H4C6H4O)-].(HOC6H4C6H4OH).2H2O. In both compounds the cations lie across centres of inversion: there are two crystallographically distinct cation sites in (1) and the conformations of the cations occupying them are quite different. In (2) the single type of cation site is occupied by a conformationally disordered cation: the major and minor components represent two further distinct conformers. In (1) the anions are linked by O-H...O hydrogen bonds into chains, and each cation is linked by a total of six N-H...O hydrogen bonds to anions in four different chains, so linking the chains into continuous sheets. In (2) the anions and the water molecules are linked into sheets, which are further linked into a continuous three-dimensional framework by both the cations and the neutral biphenol units.
More Related Videos
Related Concept Videos
Conformations of Cyclohexane
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,...
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...
Disubstituted Cyclohexanes: cis-trans Isomerism
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
Criteria for Aromaticity and the Hückel 4n + 2 Rule
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as Hückel’s rule or the 4n + 2 rule.
Nomenclature of Aryl and Heterocyclic Amines
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group with both...

