Systematic strategy for designing immidazolium containing precursors to produce N -heterocyclic carbenes: A DFT study

Kyung Yup Baek, Ji Hye Jo, Jong Hun Moon, Juyoung Yoon, Jin Yong Lee

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Abstract

A series of cationic N-heterocyclic carbene (NHC) precursors that can be utilized as fluorescent chemosensors for carbon dioxide capture were investigated by density functional theory (DFT) calculations. Activation energy barriers for the reactions of the cationic NHC precursors and hydrogen carbonate (HCO3-) based on intrinsic reaction coordinate (IRC) profiles as well as proton affinity of the precursors were compared. The calculated proton affinity of 1-ethyl-3-methylimidazol-2-yliene was in good agreement with experimental one within the margin of error. We clarified main factors to lower the activation energy barrier based on the correlation among the number of N-heterocyclic functional group, aromatic ring size, and structural characteristics for the candidate compounds. On the basis of the results, it was verified that some of our model systems spontaneously generate NHCs without any specific catalyst.

Original languageEnglish
Pages (from-to)1878-1886
Number of pages9
JournalJournal of Organic Chemistry
Volume80
Issue number3
DOIs
StatePublished - 6 Feb 2015

Bibliographical note

Publisher Copyright:
© 2015 American Chemical Society.

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