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The Electronic Structure of Phenylene and Naphthylene Bicyclobutanes. Photoelectron spectroscopy and model calculations
Author(s) -
Gleiter Rolf,
Gubernator Klaus,
EckertMaksić Mirjana,
SpangetLarsen Jens,
Bianco Bernard,
Gandillon Gérard,
Burger Ulrich
Publication year - 1981
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.19810640508
Subject(s) - mindo , chemistry , cndo/2 , computational chemistry , atomic orbital , phenylene , naphthalene , x ray photoelectron spectroscopy , electronic structure , molecule , nuclear magnetic resonance , organic chemistry , quantum mechanics , physics , polymer , electron
The photoelectron (PE.) spectra of 1,2,3‐methenoindane ( 2 ), 1,2,3‐metheno‐2,3‐dihydro‐1 H ‐cyclopenta [ b ]naphthalene ( 3 ) and 1,2,3‐metheno‐2,3‐dihydro‐1 H ‐phenalene ( 4 ) are investigated. The PE. spectrum of 1,3‐methano‐2,3‐dihydrophenalene ( 7 ) is reported and compared with that of 4 . The experimental results are analyzed in terms of empirical correlation diagrams and the results of semiempirical MINDO/3 and CNDO/S calculations. The analysis indicates that the strong impact of the bicyclobutylene group on the spectroscopic properties of the aromatic π‐systems in 2 , 3 and 4 is due to hyperconjugative interactions involving bicyclobutane Walsh orbitals.