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A comparison of the structure and bonding in the aliphatic boronic R–B(OH)2 and borinic R–BH(OH) acids (R=H; NH2, OH, and F): a computational investigation

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Abstract

Boronic acids, R–B(OH)2, play an important role in synthetic, biological, medicinal, and materials chemistry. This investigation compares the structure and bonding surrounding the boron atoms in the simple aliphatic boronic acids, R–B(OH)2 (R=H; NH2, OH, and F), and the analogous borinic acids, R–BH(OH). Geometry optimizations were performed using second-order Møller–Plesset perturbation theory (MP2) with the Dunning–Woon aug-cc-pVTZ, aug-cc-pVQZ, and aug-cc-pV5Z basis sets; single-point CCSD(FC)/aug-cc-pVTZ//MP2(FC)/aug-cc-pVTZ level calculations were used to generate a QCI density for natural bond orbital analyses of the bonding. The optimized boron–oxygen bond lengths for the X–B–Ot–H trans-branch of the endo-exo form of the boronic acids and for the X–B–O–H cis-branch of the boronic and borinic acids (X=N, O, and F, respectively) decrease as the electronegativity of X increases. The boron–oxygen bond lengths are generally longer in the endo-exo or anti forms of the boronic acids than in the corresponding borinic acids. NBO analyses suggest the boron–oxygen bond in H2BOH is a double bond; the boron–oxygen bonding in the remaining boronic and borinic acids in this study has a significant contribution from dative pπ–pπ bonding. Values for Δ\({\text{H}}_{298}^{0}\) for the highly balanced reaction, R–B(OH)2 + R–BH2 → 2 R–BH(OH), suggest that the bonding surrounding the boron atom is stronger in the borinic acid than in the corresponding boronic acid.

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Acknowledgments

This research was supported in part by the National Science Foundation through XSEDE resources provided by the XSEDE Science Gateways program. The PQS Cluster Facility at Philadelphia University was also used for the calculations described in this manuscript. J.D.L. would like to thank the National Institutes of Health for research support (Grant: 5K22HL113045-04).

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  1. Department of Chemistry and Biochemistry, College of Science, Health and the Liberal Arts, Philadelphia University, 4201 Henry Avenue, Philadelphia, PA, 19144, USA

    Niny Z. Rao & Charles W. Bock

  2. Chemistry Department, Eckerd College, 4200 54th Avenue South, St. Petersburg, FL, 33711, USA

    Joseph D. Larkin

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Correspondence to Niny Z. Rao.

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Rao, N.Z., Larkin, J.D. & Bock, C.W. A comparison of the structure and bonding in the aliphatic boronic R–B(OH)2 and borinic R–BH(OH) acids (R=H; NH2, OH, and F): a computational investigation. Struct Chem 27, 1081–1091 (2016). https://doi.org/10.1007/s11224-015-0730-5

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