A Rhenium–Cyclohexane Complex with Preferential Binding of Axial CH Bonds: A Probe into the Relative Ability of CH, CD, and CC Bonds as Hyperconjugative Electron Donors? | Zendy

Lawes Douglas J. | Zendy; Darwish Tamim A. | Zendy; Clark Timothy | Zendy; Harper Jason B. | Zendy; Ball Graham E. | Zendy

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A Rhenium–Cyclohexane Complex with Preferential Binding of Axial CH Bonds: A Probe into the Relative Ability of CH, CD, and CC Bonds as Hyperconjugative Electron Donors?

Author(s) -

Lawes Douglas J.,

Darwish Tamim A.,

Clark Timothy,

Harper Jason B.,

Ball Graham E.

Publication year - 2006

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200600313

Subject(s) - cyclohexane , chemistry , hyperconjugation , rhenium , proton , crystallography , electron , stereochemistry , molecule , inorganic chemistry , organic chemistry , physics , quantum mechanics

Which bonds bind better? According to NMR experiments with the alkane complex [CpRe(CO) 2 (cyclohexane)] at low temperatures, complexation with an axial proton is preferred over that through an equatorial one by about 1.5 kJ mol −1 . Calculations support this order of binding energies. The preference is proposed to be due to stronger electron donation through hyperconjugation from a CH bond than from a CC bond.

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