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Trapping CO 2 by Adduct Formation with Nitrogen Heterocyclic Carbenes (NHCs): A Theoretical Study
Author(s) -
Alkorta Ibon,
MonteroCampillo M. Merced,
Elguero José
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701444
Subject(s) - carbene , covalent bond , chemistry , adduct , non covalent interactions , exothermic reaction , azole , computational chemistry , nitrogen , reaction coordinate , molecule , organic chemistry , catalysis , antifungal , medicine , hydrogen bond , dermatology
Carbon dioxide can form compounds with nitrogen heterocyclic carbenes (NHCs) based on azoles through noncovalent interactions or by covalent bonding. A narrow dependence on the carbene structure has been observed for the preference for one or the other type of bonding, as revealed by a series of physicochemical descriptors. In our survey, a set of NHCs based on the azole family (three classical, three abnormal, and one remote) was shown to bind CO 2 at the accurate G4MP2 computational level. In most cases, exothermic reaction profiles towards the covalently bound form were found, which reached stabilization enthalpies of up to −77 kJ mol −1 for the remote carbene case. Both noncovalent and covalent minima and the corresponding transition state that connects them have been identified as stationary points along the reaction coordinate.