Near Cancellation of Through Space and Through Bond Interaction in bicyclo[3.2.2]nona‐6,8‐diene | Zendy

Goldstein M. J. | Zendy; Natowsky S. | Zendy; Heilbronner Edgar | Zendy; Hornung V. | Zendy

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Near Cancellation of Through Space and Through Bond Interaction in bicyclo[3.2.2]nona‐6,8‐diene

Author(s) -

Goldstein M. J.,

Natowsky S.,

Heilbronner Edgar,

Hornung V.

Publication year - 1973

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19730560120

Subject(s) - chemistry , diene , bicyclic molecule , nonane , atomic orbital , phase (matter) , space (punctuation) , stereochemistry , crystallography , quantum mechanics , organic chemistry , physics , linguistics , natural rubber , philosophy , electron

The photoelectron spectra of bicyclo[3.2.2]nonane and its five dehydrogenated analogues are reported. Analysis of the π‐bands reveals that the unsymmetrical diene 5 retains the ‘natural order’ of the π‐orbitals present in the lower homologues, i. e. the in‐phase below the out‐of‐phase combination of the basis π‐orbitals π a and π c . The isomeric diene 4 is the first member of the symmetrical homologous series ( I ), which inverts this order, so that a 1 (π) (in phase!) lies above b 2 (π) (out‐of‐phase!).

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