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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
Abstract 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!).