Quantifying the Electronic and Steric Properties of 1,3-ImidazoleBased Mesoionic Carbenes (iMICs)

Merschel A, Rottschäfer D, Neumann B, Stammler H-G, Ghadwal R (2020)
ORGANOMETALLICS 39(10): 1719-1729.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
1,3-Imidazole-based mesoionic carbenes (iMICs) are a very promising class of carbon-donor ligands in synthesis and catalysis. However, a systematic study of the quantification of stereoelectronic properties of iMICs is lacking. This is most likely due to the absence of rational synthetic routes to suitable iMIC compounds. Herein, we report the synthesis of the appropriate phosphinidene (iMIC(Ar))9PPh (iMIC(Ar) = :CCH(NDipp)(2)CAr; Ar = Ph (5a), DMP (5b); DMP = 4-Me2NC6H4; Dipp = 2,6-iPr(2)C(6)H(3)), selenium (iMIC(Ar))Se (Ar = Ph (6a), DMP (6b)), and nickel carbonyl compounds (iMIC(Ar))Ni(CO)(3)(Ar = Ph (7a), DMP (7b)). The pi-accepting property of iMIC(Ar) (Ar = Ph (2a), DMP (2b)) has been evaluated by P-31 and Se-77 NMR spectroscopic analyses of 5 and 6, respectively. The overall donor property of 2 has been assessed by determining the Tolman electronic parameter (TEP) of 7. Studies suggest that iMIC(Ar) (2) are stronger 6 donors and weaker it acceptors compared to classical N-heterocyclic carbenes (NHCs). The steric profile of iMIC(Ar) (2) has been obtained by calculating the percentage buried volume (%V-bur) for (iMIC(Ar))CuX (Ar Ph, X = I (8a); Ar = DMP, X = Br (8b)).
Erscheinungsjahr
2020
Zeitschriftentitel
ORGANOMETALLICS
Band
39
Ausgabe
10
Seite(n)
1719-1729
ISSN
0276-7333
eISSN
1520-6041
Page URI
https://pub.uni-bielefeld.de/record/2944521

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Merschel A, Rottschäfer D, Neumann B, Stammler H-G, Ghadwal R. Quantifying the Electronic and Steric Properties of 1,3-ImidazoleBased Mesoionic Carbenes (iMICs). ORGANOMETALLICS. 2020;39(10):1719-1729.
Merschel, A., Rottschäfer, D., Neumann, B., Stammler, H. - G., & Ghadwal, R. (2020). Quantifying the Electronic and Steric Properties of 1,3-ImidazoleBased Mesoionic Carbenes (iMICs). ORGANOMETALLICS, 39(10), 1719-1729. doi:10.1021/acs.organomet.0c00045
Merschel, A., Rottschäfer, D., Neumann, B., Stammler, H. - G., and Ghadwal, R. (2020). Quantifying the Electronic and Steric Properties of 1,3-ImidazoleBased Mesoionic Carbenes (iMICs). ORGANOMETALLICS 39, 1719-1729.
Merschel, A., et al., 2020. Quantifying the Electronic and Steric Properties of 1,3-ImidazoleBased Mesoionic Carbenes (iMICs). ORGANOMETALLICS, 39(10), p 1719-1729.
A. Merschel, et al., “Quantifying the Electronic and Steric Properties of 1,3-ImidazoleBased Mesoionic Carbenes (iMICs)”, ORGANOMETALLICS, vol. 39, 2020, pp. 1719-1729.
Merschel, A., Rottschäfer, D., Neumann, B., Stammler, H.-G., Ghadwal, R.: Quantifying the Electronic and Steric Properties of 1,3-ImidazoleBased Mesoionic Carbenes (iMICs). ORGANOMETALLICS. 39, 1719-1729 (2020).
Merschel, Arne, Rottschäfer, Dennis, Neumann, Beate, Stammler, Hans-Georg, and Ghadwal, Rajendra. “Quantifying the Electronic and Steric Properties of 1,3-ImidazoleBased Mesoionic Carbenes (iMICs)”. ORGANOMETALLICS 39.10 (2020): 1719-1729.