Exploring the Limits of Intramolecular London Dispersion Stabilization with 
Bulky Dispersion Energy Donors in Alkane Solution

Schümann, Jan M.; Ochmann, Lukas; Becker, Jonathan; Altun, Ahmet; Harden, Ingolf; Bistoni, Giovanni; Schreiner, Peter R.

doi:10.1021/jacs.2c13301

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Exploring the Limits of Intramolecular London Dispersion Stabilization with Bulky Dispersion Energy Donors in Alkane Solution

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Altun, Ahmet
Research Group Bistoni, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Harden, Ingolf
Research Group Bistoni, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Bistoni, Giovanni
Research Group Bistoni, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Dipartmento di Chimica, Biologia e Biotechnologie, Università Degli Studi Di Perugia;

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Citation

Schümann, J. M., Ochmann, L., Becker, J., Altun, A., Harden, I., Bistoni, G., et al. (2023). Exploring the Limits of Intramolecular London Dispersion Stabilization with Bulky Dispersion Energy Donors in Alkane Solution. Journal of the American Chemical Society, 145(4), 2093-2097. doi:10.1021/jacs.2c13301.

Cite as: https://hdl.handle.net/21.11116/0000-000C-9646-C

Abstract

We present an experimental study of a cyclooctatetraene-based molecular balance disubstituted with increasingly bulky tert-butyl (tBu), adamantyl (Ad), and diamantyl (Dia) substituents in the 1,4-/1,6-positions for which we determined the valence-bond shift equilibrium in n-hexane (hex), n-octane (oct), and n-dodecane (dod). Computations including implicit and explicit solvation support our temperature-dependent NMR equilibrium measurements indicating that the more sterically crowded 1,6-isomer is always favored, irrespective of solvent, and that the free energy is quite insensitive to substituent size.