Abstract
Classical cyclophanes with two benzene rings have been compared with cyclophanes with one benzene ring replaced with an aliphatic part and aliphatic compounds, which are cyclophane analogues. Analysis of geometry, atomic charges, and aromatic and steric energy and investigation of intramolecular noncovalent interactions and charge mobility show that there is no special feature that distinguishes the classical cyclophanes from aliphatic analogues, so the definition of cyclophanes can be extended to other compounds.
Highlights
Cyclophanes are hydrocarbons of immense structural diversity containing aromatic units and an aliphatic chain that forms a bridge between two non-adjacent positions of the aromatic ring.[1,2]
Most typical are the cyclophanes having two benzene rings joined by aliphatic bridges between the para and/or meta positions of the aromatic rings
The cyclophanes can be designed as compounds having an assembly of aromatic rings and aliphatic chains as alternate components of a large ring
Summary
Cyclophanes are hydrocarbons of immense structural diversity containing aromatic units (typically benzene rings) and an aliphatic chain that forms a bridge between two non-adjacent positions of the aromatic ring.[1,2] Most typical are the cyclophanes having two benzene rings joined by aliphatic bridges between the para and/or meta positions of the aromatic rings. In the other group of cyclophanes, one benzene ring is replaced by an aliphatic part. In [n]cyclophanes (n is the number of methylene groups), the oligomethylene bridges connect the para or meta positions in benzene; in the so-called “araliphanes”, the ethylene bridges join the aromatic and aliphatic rings. The cyclophanes can be designed as compounds having an assembly of aromatic rings and aliphatic chains as alternate components of a large ring. Multitude aromatic units and bridges form cagelike structures.[3]
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