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Citation: WANG Wen-Feng, YUAN Yao-Feng, LI Jun-Qian. A DFT Study on the Rearrangement of Carbanion[J]. University Chemistry, ;2017, 32(8): 60-65. doi: 10.3866/PKU.DXHX201701017 shu

A DFT Study on the Rearrangement of Carbanion

College of Chemistry, Fuzhou University, Fuzhou 350116, P. R. China

The molecular orbitals of transition states of 1,2-shift and 1,4-shift of carbanion were calculated using the density functional theory (DFT) method. It was found that the migration atom carried positive charge and the rest of the carbanion became a double carbanion. In the transition state of 1,2-shift, the phase of HOMO of the double carbanion doesn't match that of LUMO of the migration atom. However, in the transition state of 1,4-shift, the phase of HOMO of the double carbanion matches that of LUMO of the migration atom. So the 1,2-shift of carbanion is an orbital symmetry prohibited reaction and the 1,4-shift of carbanion is an orbital symmetry permitted reaction. The calculation in this paper can afford a valuable reference for the teaching of advanced organic chemistry.
- Carbanion,
- Rearrangement,
- Orbital symmetry,
- Chemical calculation
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