Abstract
Metal-catalyzed hydrogen atom transfer (MHAT) reactions are widely used and nowadays constitute a large class of chemically catalyzed reactions and provide a convenient way to obtain various chemical products and synthesize building blocks. The cobalt compound has been identified as an effective catalyst for MHAT reactions due to its low cost, high abundance, high efficiency and high selectivity, in which the cobalt hydride is an indispensable catalytic active intermediate, and the breakage of cobalt-hydrogen bonds is crucial for the reaction to proceed. Therefore, the Co–H bond dissociation enthalpy (BDE) becomes an extremely significant thermodynamic property. In this report, the Co–H BDEs of some cobalt hydrides were calculated with experimental values by using ten DFT functionals, and the results show that the B97D functional gave the optimal precision with a root mean square error (RMSE) of 3.1 kcal/mol. Next, the BDEs and substituent effects of ten kinds of cobalt hydrides were further investigated. The results show that ligands may remarkably influence the Co–H BDEs and substituent effects on Co-H BDEs vary in different kinds of cobalt hydrides. In addition, analyses on the natural bond orbital (NBO) and the energies of frontier orbitals were performed to reveal more about the variation patterns of the Co–H BDE.
Similar content being viewed by others
REFERENCES
S. A. Green, S. W. M. Crossley, J. L. M. Matos, et al., Acc. Chem. Res. 51, 2628 (2018).
W. Y. Ai, R. Zhong, X. F. Liu, et al., Chem. Rev. (Washington, DC, U. S.) 119, 2876 (2019).
E. S. Wiedner, M. B. Chambers, C. L. Pitman, et al., Chem. Rev. (Washington, DC, U. S.) 116, 8655 (2016).
H. Adkins and G. Krsek, J. Am. Chem. Soc. 71, 3051 (1949).
P. J. Chirik, Acc. Chem. Res. 48, 1687 (2015).
Y. Y. Li, S. L. Yu, W. Y. Shen, et al., Acc. Chem. Res. 48, 2587 (2015).
K. Gao and N. Yoshikai, Acc. Chem. Res. 47, 1208 (2014).
G. A. Filonenko, R. van Putten, E. J. M. Hensen, et al., Chem. Soc. Rev. 47, 1459 (2018).
J. Sun and L. Deng, Catal. Commun. 6, 290 (2015).
X. Y. Du and Z. Huang, Catal. Commun. 7, 1227 (2017).
J. V. Obligacion and P. J. Chirik, Rev. Analg. 2, 15 (2018).
Z. Huang, Z. Q. Zuo, H. N. Wen, et al., Synlett 29, 1421 (2018).
J. H. Chen and Z. Lu, Org. Chem. Front. 5, 260 (2018).
V. van der Puyl, R. O. McCourt, and R. A. Shenvi, Tetrahedron Lett. 72, 153047 (2021).
M. H. Guan, H. R. Miao, T. Qin, et al., Chem. Commun. 58, 13023 (2022).
D. Vrubliauskas, B. M. Gross, and C. D. Vanderwal, J. Am. Chem. Soc. 143, 2944 (2021).
Y. Ji, Z. Y. Xin, H. B. He, et al., J. Am. Chem. Soc. 141, 16208 (2019).
B. S. Freiser, Organometallic Ion Chemistry (Springer, New York, 2012).
J. T. Landrum and C. D. Hoff, J. Organomet. Chem. 282, 215 (1985).
J. A. Connor, M. T. Zafarani-Moattar, J. Bickerton, et al., Organometallics 1, 1166 (1982).
K. Tokmic and A. R. Fout, J. Am. Chem. Soc. 138, 13700 (2016).
X. J. Qi, Z. Li, Y. Fu, et al., Organometallics 27, 2688 (2008).
L. Y. Shi, X. L. Lv, J. F. Weng, et al., Crop J. 2, 132 (2014).
E. Clot, C. Megret, O. Eisenstein, et al., J. Am. Chem. Soc. 131, 7817 (2009).
D. Devarajan, T. B. Gunnoe, and D. H. Ess, Inorg. Chem. (Washington, DC, U. S.) 51, 6710 (2012).
J. Uddin, C. M. Morales, J. H. Maynard, et al., Organometallics 25, 5566 (2006).
S. J. Blanksby and G. B. Ellison, Acc. Chem. Res. 36, 255 (2003).
Y. H. Cheng, X. Zhao, K. S. Song, et al., J. Org. Chem. 67, 6638 (2002).
K. S. Song, L. Liu, and Q. X. Guo, J. Org. Chem. 68, 4604 (2003).
G. T. Bae, B. Dellinger, and R. W. Hall, J. Phys. Chem. A 115, 2087 (2011).
J. Hsiao and M.-D. Su, Organometallics 26, 4432 (2007).
C. R. Landis, S. Feldgus, J. Uddin, et al., Organometallics 19, 4878 (2000).
J.-H. Sheu and M.-D. Su, J. Organomet. Chem. 696, 1221 (2011).
O. Gutierrez and D. J. Tantillo, Organometallics 29, 3541 (2010).
C. Trinh, A. Y. Timoshkin, and G. Frenking, J. Phys. Chem. A 113, 3420 (2009).
M.-D. Su and S.-Y. Chu, J. Phys. Chem. A 105, 3591 (2001).
O. Gutierrez and M. C. Kozlowski, in Understanding Organometallic Reaction Mechanisms and Catalysis, Ed. by V. A. Ananikov (Wiley, New York, 2014), p. 93.
M. Dolg, U. Wedig, H. Stoll, et al., J. Chem. Phys. 86, 866 (1987).
D. Andrae, U. Haeussermann, M. Dolg, et al., Theor. Chim. Acta 77, 123 (1990).
A. V. Marenich, C. J. Cramer, and D. G. Truhlar, J. Phys. Chem. B 113, 4538 (2009).
C. Lee, W. T. Yang, and R. G. Parr, Phys. Rev. B 37, 785 (1988).
J. P. Perdew, Phys. Rev. B 33, 8822 (1986).
S. Grimme, J. Comput. Chem. 27, 1787 (2006).
A. Austin, G. A. Petersson, M. J. Frisch, et al., J. Chem. Theory Comput. 8, 4989 (2012).
J.-D. Chai and M. Head-Gordon, Chem. Phys. Lett. 467, 176 (2008).
J. D. Chai and M. Head-Gordon, Phys. Chem. Chem. Phys. 10, 6615 (2008).
Y. Zhao, N. E. Schultz, and D. G. Truhlar, J. Chem. Theory Comput. 2, 364 (2006).
Y. Zhao and D. G. Truhlar, Acc. Chem. Res. 41, 157 (2008).
H. Hirao, J. Phys. Chem. A 115, 9308 (2011).
J. Yang and M. P. Waller, J. Phys. Chem. A 117, 174 (2013).
A. E. Reed, L. A. Curtiss, and F. Weinhold, Chem. Rev. 88, 899 (1988).
M. J. Frisch, G. W. Trucks, H. B. Schlegel, et al., Gaussian (Wallingford, CT, 2016).
J. Halpern, Discuss. Faraday Soc. 46, 1 (1968).
P. B. Armentrout and L. S. Sunderlin, in Transition Metal Hydrides, Ed. by A. Dedieu (VCH, New York, 1992).
P. B. Armentrout and B. L. Kickel, Organometallic Ion Chemistry (Kluwer, Dordrecht, 1996), p. 1.
M. Tilset and V. D. Parker, J. Am. Chem. Soc. 111, 6711 (1989).
C. C. H. Atienza, T. Diao, K. J. Weller, et al., J. Am. Chem. Soc. 136, 12108 (2014).
A. D. Ibrahim, S. W. Entsminger, and A. R. Fout, ACS Catal. 7, 3730 (2017).
K. Duvvuri, K. R. Dewese, M. M. Parsutkar, et al., J. Am. Chem. Soc. 141, 7365 (2019).
J. H. Chen, J. Guo, Z. Lu, Chin. J. Chem. 36, 1075 (2018).
M. S. Jeletic, M. T. Mock, A. M. Appel, et al., J. Am. Chem. Soc. 135, 11533 (2013).
H. Shigehisa, Synlett 26, 2479 (2015).
T. Yamada, Synthesis 2008, 1628 (2008).
J.-i. Setsune, Y. Ishimaru, T. Moriyama, et al., J. Chem. Soc. Pak., 555 (1991).
T. Okamoto and S. Oka, Tetrahedron Lett. 22, 2191 (1981).
G. Li, A. Han, M. E. Pulling, et al., J. Am. Chem. Soc. 134, 14662 (2012).
ACKNOWLEDGMENTS
We thank the Shanghai Supercomputer Center for the computational resources.
Funding
This work was supported by ongoing institutional funding. No additional grants to carry out or direct this particular research were obtained.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare that they have no conflicts of interest.
Supplementary Information
Rights and permissions
About this article
Cite this article
Ren, L., Zheng, W., Yang, Y. et al. DFT Study on Co–H Bond Dissociation Enthalpies of Cobalt Hydrides in Metal-Catalyzed Hydrogen Atom Transfer Reactions. Russ. J. Phys. Chem. 97, 2755–2767 (2023). https://doi.org/10.1134/S0036024423120208
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0036024423120208