Abstract
In order to furnish a reliable interpretation of the1H-NMR spectrum of [2.2]metacyclophane (1) based on the ring current theory two basic conditions must be fullfilled:
-
1.
Bond lengths angle deformations due to the puckered topology of the molecule must be taken into account. The geometry parameters can be deduced fromX-ray data.
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2.
The (fictive) reference chemical shift of the system (i.e. unperturbed by the “second” benzene ring) must be established since the Δ δ's ofBovey's ring current formula have to be related to a reference.
The shifts calculated on the basis of these assumptions are in agreement with the actual spectrum.
Moreover, it can be shown that for basic reasons a quantitative approach to the chemical shift of the methylene protons in the bridgevia ring current theory is impossible.
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Glotzmann, C., Langer, E. & Lehner, H. Zur diamagnetischen Anisotropie im [2.2]Metacyclophan. Monatshefte für Chemie 105, 354–361 (1974). https://doi.org/10.1007/BF00907384
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DOI: https://doi.org/10.1007/BF00907384