Computational study on the stability of imidazol-2-ylidenes and imidazolin-2-ylidenes

Mu Jeng Cheng, Ching Han Hu

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33 Citations (Scopus)


The dimerization reactions of 12 cyclic diaminocarbenes have been studied using density functional theory (DFT). The activation energies (Ea) and reaction energies (ΔE) for the dimerizations of imidazol-2-ylidenes are larger than those of imidazolin-2-ylidenes. It was observed that Ea of dimerization is approximately proportional to the singlet-triplet energy separation (ΔES-T), aromatic stabilization energy (ASE), and ΔE of the carbene. Excellent linear correlation is seen between Ea and ASE. Contrary to previous suggestions, we found that 4,5-dichloro substitutions decrease the stability of imidazol(in)-2-ylidenes. Steric effects on Ea occur noticeably as isopropyl (i-Pr) substitutions are introduced to the carbenes.

Original languageEnglish
Pages (from-to)477-482
Number of pages6
JournalChemical Physics Letters
Issue number5-6
Publication statusPublished - 2001 Dec 7

All Science Journal Classification (ASJC) codes

  • Physics and Astronomy(all)
  • Physical and Theoretical Chemistry

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