Comparative Lewis Acidity\nin Fluoroarylboranes: B(<i>o</i>‑HC<sub>6</sub>F<sub>4</sub>)<sub>3</sub>, B(<i>p</i>‑HC<sub>6</sub>F<sub>4</sub>)<sub>3</sub>, and B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>
MatthewM. Morgan (2003758)Adam J. V. Marwitz (2003755)Warren E. Piers (1569994)Masood Parvez (1569997)
Abstract
The Lewis acidic fluoroarylborane B(<i>o</i>-HC<sub>6</sub>F<sub>4</sub>)<sub>3</sub> (<b>2</b>) was prepared\nand its Lewis acid strength assessed in comparison to the known, related\nboranes B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> (<b>1</b>)\nand B(<i>p</i>-HC<sub>6</sub>F<sub>4</sub>)<sub>3</sub> (<b>3</b>). Experimental methods based on spectroscopic probes and\nequilibrium measurements were used to show that B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> is the strongest Lewis acid of the three; while\nthe Lewis acidities of <b>2</b> and <b>3</b> are comparable,\nthe <i>p</i>-H-substituted isomer is slightly stronger in\nthe tests employed. This contrasts with predictions made on the basis\nof computed bond formation energies, as recently reported by Durfey\nand Gilbert.
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