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Theoretical Study of the Structure and the Physico Chemical Properties of 1,2‐Benzyne
Author(s) -
Haselbach E.
Publication year - 1971
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.19710540726
Subject(s) - chemistry , mindo , aryne , acetylene , bent molecular geometry , bond energy , mole , computational chemistry , bond length , molecular geometry , standard enthalpy of formation , strain energy , thermochemistry , total energy , molecule , thermodynamics , organic chemistry , physics , finite element method , psychology , displacement (psychology) , psychotherapist
The structure of 1,2‐benzyne (I) has been optimized with respect to its total molecular energy using the MINDO/2 SCF‐procedure. The results indicate a bond length of ∼1.26 Å for the strained triple bond. The overall geometry suggests that I possesses considerable resonance energy. The calculated heat of formation (Δ Hf (I) = 107 kcal/mole) is in good agreement with an estimate from mass spectrometric studies (Δ Hf exp (I) = 118 ± 5 kcal/mole). From model calculations for bent acetylene the strain energy of I is estimated to be about 60 kcl/mole. Some chemical reactions of I are discussed in the light of the results.