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 language | English |
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Pages (from-to) | 1878-1886 |
Number of pages | 9 |
Journal | Journal of Organic Chemistry |
Volume | 80 |
Issue number | 3 |
DOIs | |
State | Published - 6 Feb 2015 |
Bibliographical note
Publisher Copyright:© 2015 American Chemical Society.