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Quantification of CH⋅⋅⋅π Interactions: Implications on How Substituent Effects Influence Aromatic Interactions |
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| Authors: | Prof. Dr. Benjamin W. Gung Bright U. Emenike Prof. Dr. Michael Lewis Prof. Dr. Kristin Kirschbaum |
| Affiliation: | 1. Department of Chemistry and Biochemistry, Miami University, Oxford, Ohio 45056 (USA), Fax: (+1)?513‐529‐5715;2. Department of Chemistry, Saint Louis University, Saint Louis, MO 63103 (USA);3. Department of Chemistry, University of Toledo, Toledo, Ohio 43606 (USA) |
| Abstract: | Attractive interactions between a substituted benzene ring and an α‐substituted acetate group were determined experimentally by using the triptycene model system. The attractive interaction correlates well with the Hammett constants σm (R2=0.90), but correlates much better with the acidity of the α‐protons (R2=0.98). |
| Keywords: | aromatic interactions computational chemistry Hammett plots substituent effects triptycenes |