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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 22, Number 10
BKCSDE 22(10)
October 20, 2001 

The Reactivity and Stability Studies of Benzoquinone Methides by Ab Initio Calculations
Woonphil Baik, Shin Jong Kim, Eun-young Hurh, Sangho Koo, Byeong Hyo Kim
Benzoquinone methide, Ab initio, B3LYP.
The conformations of symmetrically hindered benzoquinone methides (=BMs), unsymmetrically hindered BMs, and simple BM have been optimized using density functional theories. It is shown that the optimized geometries of symmetrically hindered BMs are fully in accord with those expected for the plannar conformations, in which the effective hyperconjugation of symmetrically substituted dialky groups with ring can occur. Relative stabilization energies calculated at the B3LYP/6-31G*//B3LYP/6-31* level by means of isodesmic equation are 2.8-5.3 kcal/mol enhanced for symmetrically hindered BMs. This finding provides a rationalization for the previous experimental results that the BM formation is depend upon the substituents.
1127 - 1130
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