Computed ammonia affinity for evaluating Lewis acidity of organoboronates and organoboronamides

Hideya Tanaka; Masaaki Nakamoto; Hiroto Yoshida

doi:10.1039/d2ra07826k

Computed ammonia affinity for evaluating Lewis acidity of organoboronates and organoboronamides

RSC Adv. 2023 Jan 17;13(4):2451-2457. doi: 10.1039/d2ra07826k. eCollection 2023 Jan 11.

Authors

Hideya Tanaka¹, Masaaki Nakamoto¹, Hiroto Yoshida¹

Affiliation

¹ Graduate School of Advanced Science and Engineering, Hiroshima University Higashi-Hiroshima 739-8526 Japan yhiroto@hiroshima-u.ac.jp.

Abstract

Lewis acidity of organoboronates [B(pin), B(neop), B(cat), B(eg), B(nad)] and organoboronamides [B(dan), B(aam), B(mdan)] has been found to be unifiedly evaluated by computed ammonia affinity (AA), while other methods [LUMO energies, global electrophilicity index (GEI), fluoride ion affinity (FIA)] were only partially applicable. The relationships between the AA values and such structural characters including the B-X bond lengths, the X-B-X angles, and the changes in the B-X bond lengths in the formation of the ammonia adducts were also described.