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Barrier to 1,3‐sigmatropic shift in odd electron ions. A MINDO/3 study of H, OH, CH 3 and C 6 H 5 migration
Author(s) -
Hoppilliard Y.,
Bouchoux G.
Publication year - 1982
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210171014
Subject(s) - mindo , ion , sigmatropic reaction , thermochemistry , chemistry , electron , computational chemistry , stereochemistry , physics , molecule , organic chemistry , nuclear physics
Critical energies for 1,3‐R sigmatropic migrations (RH, OH, CH 3 and C 6 H 5 ) have been calculated by means of the MINDO/3 method. This investigation was carried out for the system [RCH 2 CHCH 2 ] +˙ and the results indicated that hydroxyl group migration is energetically favoured (critical energy = 53 kJ mol −1 ). Calculations are also presented for [3‐buten‐2‐ol] +˙ isomerizations. The lowest energy pathway is related to the [2‐buten‐1‐ol] +˙ ; the corresponding critical energy for OH migration is equal to 33 kJ mol −1 in this case.