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Propella[3 4 ] prismane and its congeners: A MO‐theoretical study
Author(s) -
Gleiter Rolf,
Pfeifer KarlHeinz,
Koch Wolfram
Publication year - 1995
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/jcc.540160104
Subject(s) - mindo , mndo , chemistry , ab initio , computational chemistry , molecular orbital , cycloaddition , atomic orbital , diene , bond length , crystallography , stereochemistry , physics , molecule , quantum mechanics , organic chemistry , crystal structure , natural rubber , catalysis , electron
The geometries of a fourfold bridged tricyclo[4.2.0.0 2,5 ]octa‐3,7‐diene ( 1 ) and its photoproducts 2 and 3 were calculated by Hartree‐Fock ab initio (3‐21G and DZP basis) and semiempirical (MNDO, AM1, MINDO /3) methods. It was found that due to the smaller distance between the double bonds in 1 (2.65 Å) as compared to the parent tricyclo[4.2.0.0 2,5 ]octa‐3,7‐diene ( 4 ) (2.91 Å), the sequence of the frontier orbitals is different. In the case of 1 , the photochemical [2 + 2]cycloaddition is allowed, whereas in 4 it is forbidden. © 1995 by John Wiley & Sons, Inc.