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Chalcogen Bonding in Solution: Interactions of Benzotelluradiazoles with Anionic and Uncharged Lewis Bases
Abstract
Chalcogen bonding is the noncovalent interaction between an electron-deficient, covalently bonded chalcogen (Te, Se, S) and a Lewis base. Although substantial evidence supports the existence of chalcogen bonding in the solid state, quantitative data regarding the strengths of the interactions in the solution phase are lacking. Herein, determinations of the association constants of benzotelluradiazoles with a variety of Lewis bases (Cl(-), Br(-), I(-), NO3(-) and quinuclidine, in organic solvent) are described. The participation of the benzotelluradiazoles in chalcogen bonding interactions was probed by UV-vis, (1)H and (19)F NMR spectroscopy as well as nano-ESI mass spectrometry. Trends in the free energy of chalcogen bonds upon variation of the donor, acceptor and solvent are evident from these data, including a linear free energy relationship between chalcogen bond donor ability and calculated electrostatic potential at the tellurium center. Calculations using the dispersion-corrected B97-D3 functional were found to give good agreement with the experimental free energies of chalcogen bonding.
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Citations
Cites
Effect of the damping function in dispersion corrected density functional theory
Grimme, S., Ehrlich, S., & Goerigk, L. (2011) · Journal of Computational Chemistry · doi:10.1002/jcc.21759 · Cited by 28,221
Cited by
Chalcogen bonding in synthesis, catalysis and design of materials
Mahmudov, K. T., Kopylovich, M. N., Guedes da Silva, M. F. C., & Pombeiro, A. J. L. (2017) · Dalton Transactions · doi:10.1039/c7dt01685a · Cited by 466
Sigma-Hole Interactions in Anion Recognition
Lim, J. Y. C., & Beer, P. D. (2018) · Chem · doi:10.1016/j.chempr.2018.02.022 · Cited by 428
Anion Recognition Strategies Based on Combined Noncovalent Interactions
Molina, P., Zapata, F., & Caballero, A. (2017) · Chemical Reviews · doi:10.1021/acs.chemrev.6b00814 · Cited by 406
Anion Transport with Chalcogen Bonds
Benz, S., Macchione, M., Verolet, Q., Mareda, J., Sakai, N., & Matile, S. (2016) · Journal of the American Chemical Society · doi:10.1021/jacs.6b05779 · Cited by 297
Chalcogen-bond driven molecular recognition at work
Biot, N., & Bonifazi, D. (2020) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2020.213243 · Cited by 266
Metadata
- Authors
- Garrett, G. E., Gibson, G. L., Straus, R. N., Seferos, D. S., & Taylor, M. S.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2015-03-17
- Volume
- 137
- Issue
- 12
- Pages
- 4126-4133
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2319773935
- Cited by
- 290
- References
- 1
- FWCI
- 19.88
- Type
- journal article
- Language
- en
- Open access
- closed
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