Publications [#233442] of Andrew T. McPhail

Journal Articles

  1. Spielvogel, BF; McPhail, AT; Knight, JA; Moreland, CG; Gatchell, CL; Morse, KW, "Predictive Schemes for Reactivity of Borane Carbonyl and the Stabiity of Carbonyltrihydroborate Anions, BH3C(O)X¯", Polyhedron, 1983, 2(12), 1345-1352, Elsevier BV [Gateway.cgi], [doi].
    (last updated on 2026/01/21)

    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. © 1983.