The reactivity and stability studies of benzoquinone methides by ab initiocalculations

Citation
W. Baik et al., The reactivity and stability studies of benzoquinone methides by ab initiocalculations, B KOR CHEM, 22(10), 2001, pp. 1127-1130
Citations number
45
Categorie Soggetti
Chemistry
Journal title
BULLETIN OF THE KOREAN CHEMICAL SOCIETY
ISSN journal
02532964 → ACNP
Volume
22
Issue
10
Year of publication
2001
Pages
1127 - 1130
Database
ISI
SICI code
0253-2964(20011020)22:10<1127:TRASSO>2.0.ZU;2-1
Abstract
The conformations of symmetrically hindered benzoquinone methides (=BMs), u nsymmetrically hindered BMs, and simple BM have been optimized using densit y functional theories. It is shown that the optimized geometries of symmetr ically hindered BMs are fully in accord with those expected for the plannar conformations, in which the effective hyperconjugation of symmetrically su bstituted dialky groups with ring can occur. Relative stabilization energie s calculated at the B3LYP/6-31G*//B3LYP/6-31* level by means of isodesmic e quation are 2.8-5.3 kcal/mol enhanced for symmetrically hindered BMs. This finding provides a rationalization for the previous experimental results th at the BM formation is depend upon the substituents.