Abstract
The reactivity of borane carbonyl (BH3CO) and its isoelectronic counterpart the acetylium cation (CH3CO+) are compared resulting in the formulation of (carbonyl)trihydroborate anions, BH3C(O)X−, which are isoelectronic and isostructural with organic carbonyls. By analogy with the ease of reduction of organic carbonyl compounds by hydroborate, the relative stability towards self-reduction-oxidation (hydride transfer from boron to carbonyl carbon) in BH3C(O)X− is proposed. The postulated order, with increasing stability is BH3C(O)Cl− < BH3C(O)H− < BH3C(O)R− < BH3C(O)OR− < BH3C(O)NR−2 < BH3C(O)O2−. Experimental results of this study together with known chemistry are shown to be consistent with the proposed order. Further, it is suggested that a similar predictive scheme may be applicable to the chemistry of the amine-carboxyboranes (boron analogues of α-amino acids) and their derivatives.
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