Carbenes as Electron-Pair Donors To CO2 for C···C Tetrel Bonds and C-C Covalent Bonds

The Journal of Physical Chemistry. a
Janet E Del BeneJosé Elguero

Abstract

Ab initio MP2/aug'-cc-pVTZ calculations have been carried out to identify stable complexes and molecules and the transition structures that interconvert them on the potential surfaces of ten singlet carbene bases acting as electron-pair donors to CO2. The carbene bases include cyclic C(NHCH)2 or NHC, C(NH2)2, an oxygen heterocyclic carbene C(OCH)2 or OHC, C(OH)2, C(CH3)2, cyclic C3H2, CCCH2, CCl2, CCH2, and CF2. Carbene:CO2 complexes stabilized by C···C tetrel bonds have been found on all potential surfaces, whereas carbene-CO2 molecules stabilized by C-C covalent bonds have been found on eight surfaces. Three of these molecules have open structures with C2v symmetry, whereas the remaining have cyclic three membered C-O-C rings with Cs symmetry. The transition structures which connect the complex and the molecule are bound on three of the potential surfaces. Whether the transition structure is bound or unbound relative to the carbene and CO2 depends on the relationship among C-C distances at the three stationary points on the surface. Charge-transfer interactions stabilize carbene:CO2 complexes. The primary charge transfer in complexes arises from electron donation from the carbene lone-pair to the CO2 molecule. There is also b...Continue Reading

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Citations

Feb 21, 2019·Physical Chemistry Chemical Physics : PCCP·Simon Mathieu, Georges Trinquier
Feb 23, 2019·Chemistry : a European Journal·Lauren E LieskeCharles W Machan
Jun 20, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·José Luis Casals-SainzÁngel Martín Pendás
Sep 8, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Janet E Del BeneJosé Elguero
Apr 18, 2018·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Ibon AlkortaJanet E Del Bene
Sep 8, 2017·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Saber Mohammadi ChalanchiDavid Quiñonero
May 17, 2017·Chemistry : a European Journal·Ibon AlkortaJosé Elguero
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