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Electronic Structure, Molecular Conformation and Reactivity of Benzonorbornadiene Systems
Author(s) -
Haselbach Edwin,
Rossi Michel
Publication year - 1976
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.19760590134
Subject(s) - chemistry , reactivity (psychology) , atomic orbital , molecular orbital , ring (chemistry) , computational chemistry , benzene , derivative (finance) , ground state , inverse , electron , crystallography , molecule , atomic physics , quantum mechanics , organic chemistry , medicine , physics , alternative medicine , geometry , mathematics , pathology , financial economics , economics
From the photoelectron spectra of benzonorbornadiene ( 1 ) and its 9‐isopropylidene derivative ( 2 ) the energy and an approximate wave function for the highest occupied orbitals is obtained. With these results the differential reactivity of the systems in Diels‐Alder additions with ‘inverse electron demand’ is discussed on the basis of frontier orbitals. For the ground state of 2 similar non‐bonded interactions between the isopropylidene unit and the double bond or the benzene ring are indicated. Conformational equilibria in 9‐aza derivatives of 1 are discussed in view of these findings.