Stable α-heteroatom-free dialkylcarbenes: A DFT study

M. Z. Kassaee, M. R. Momeni

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2 Scopus citations


The stability of the singlet dicyclopropylcarbene (δES-T = 15.3 kcal/mol, 1) is increased not only by cyclization to 2,5- dicyclopropylcyclopentanylidene (δES-T = 20.3 kcal/mol, 2), but even more so by unsaturation to 2,5-dicyclopropylcyclopentenylidene (δES-T = 22.5 kcal/mol, 3). In a further attempt to pave the way toward synthesis of new stable dialkylcarbenes, we introduced different substituents on the a-cyclopropyls of 3, where the stability was increased over twice of 1 (δES-T = 37.8 kcal/mol) for 2,5-bis(2,3- dihydroxycyclopropyl)-3,4-dinitrocyclopentenylidene, 3OH-NO2.

Original languageEnglish (US)
Pages (from-to)141-147
Number of pages7
JournalStructural Chemistry
Issue number1
StatePublished - Feb 1 2011


  • DFT
  • Dicyclopropylcarbene
  • Hydrogen bonding
  • Stability
  • Substitution


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