1. Reaction – Nucleophilic acyl substitution Yixun Xing

2. Reaction

3. Reaction Mechanism

4. Nucleophilic Substitution— A fundamental class of substitution reaction in which an "electron rich" nucleophile selectively bonds with or attacks the positive or partially positive charge of an atom attached to a group or atom called the leaving group;substitution reactionnucleophileleaving group the positive or partially positive atom is referred to as an electrophile.electrophile

5. Nucleophilic acyl substitution— Upon attack of the nucleophile at the carbonyl group, a tetrahedral intermediate is formed with the nucleophile, the leaving group and the oxygen anion attached to the central carbon atom. The alkoxy group can now revert back to the carbonyl group and at the same time expel the leaving group.alkoxycarbonylleaving group

6. Homo:MO28 Energy: -10.89670ev Lumo:MO29 Energy: 5.31218 ev

7. Homo: MO 46 Energy: -11.52918ev Lumo:MO47 Energy: 2.89761ev

8. Energy Gap E(LUMO) -E (HOMO) = 2.89761ev-(-10.89670ev) =13.79431ev

9. Distanc e: 4.0 Å Distance: 3.5 Å

10. Distanc e: 3.0 Å Distance: 2.5 Å

11. Distance: 2.0 Å Distance: 1.8 Å

12. Distance: 1.6 Å Distance: 1.4 Å

13. Distance: 1.2 Å Distance: 1.0 Å

15. Product

16. Homo: MO 56 Energy: -11.16780ev Lumo: MO57 Energy: 2.76860ev

17. Conclusion

18. Energy Gap E(LUMO) -E (HOMO) = 2.89761ev-(-10.89670ev) =13.79431ev

19. LUMO & HOMO