Strong dissimilarities between the gas-phase acidities of saturated and alpha,beta-unsaturated boranes and the corresponding alanes and gallanes

Chemistry : a European Journal
José A GámezManuel Yáñez

Abstract

The effect that unsaturation has on the intrinsic acidity of boranes, alanes, and gallanes, was analyzed by B3 LYP and CCSD(T)/6-311+G(3df,2p) calculations on methyl-, ethyl-, vinyl-, and ethynylboranes, -alanes and -gallanes, and on the corresponding hydrides XH3. Quite unexpectedly, methylborane, which behaves as a carbon acid, is predicted to have an intrinsic acidity almost 200 kJ mol(-1) stronger than BH3, reflecting the large reinforcement of the C--B bond, which upon deprotonation becomes a double bond through the donation of the lone pair created on the carbon atom into the empty p orbital of the boron. Also unexpectedly, and for the same reason, the saturated and alpha,beta-unsaturated boranes are much stronger acids than the corresponding hydrocarbons, in spite of being carbon acids as well. The Al derivatives also behave as carbon acids, but in this case the most favorable deprotonation process occurs at C beta, leading to the formation of rather stable three-membered rings, again through the donation of the C beta lone pair into the empty p orbital of Al. For Ga-containing compounds the deprotonation of the GaH2 group is the most favorable process. Therefore only Ga derivatives behave similarly to the analogues of G...Continue Reading

References

Jun 28, 2001·Journal of the American Chemical Society·J F GalJ C Guillemin
Aug 1, 1949·Journal of Research of the National Bureau of Standards·J W KNOWLTON, F D ROSSINI

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Citations

Oct 14, 2008·Chemistry : a European Journal·Ane EizaguirreJean-Claude Guillemin
Mar 11, 2009·Chemistry : a European Journal·Marcela HurtadoJean-Claude Guillemin
May 8, 2010·Physical Chemistry Chemical Physics : PCCP·Marcela HurtadoJean-Claude Guillemin
Mar 2, 2012·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Marcela HurtadoJean-Claude Guillemin

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