A Detailed Theoretical Analysis of the 1,7‐Sigmatropic Hydrogen Shift: The Möbius Character of the Eight‐Electron Transition Structure | Zendy

Jiao Haijun | Zendy; von Ragué Schleyer Paul | Zendy

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A Detailed Theoretical Analysis of the 1,7‐Sigmatropic Hydrogen Shift: The Möbius Character of the Eight‐Electron Transition Structure

Author(s) -

Jiao Haijun,

von Ragué Schleyer Paul

Publication year - 1993

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.199317631

Subject(s) - pericyclic reaction , character (mathematics) , chemistry , sigmatropic reaction , ab initio , computational chemistry , ring (chemistry) , benzene , electron , ab initio quantum chemistry methods , crystallography , physics , stereochemistry , molecule , nuclear physics , organic chemistry , geometry , mathematics

Pronounced aromatic character is found in the helical transition structure 1 for the 1,7 H shift in (Z,Z)‐1,3,5‐heptatriene according to ab initio calculations. The CC bond lengths are similar to those in benzene, the 1 H NMR shifts (IGLO calculations) indicate strong ring current effects, and the energy of concert (roughly 60 kcal mol −1 ) is the highest reported for any pericyclic reaction.

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