Jp. Kiplinger et al., GAS-PHASE ION-MOLECULE CHEMISTRY OF BORATE AND BORONATE ESTERS, Journal of the American Society for Mass Spectrometry, 5(3), 1994, pp. 169-176
Borate esters B(OR)3 and boronate esters RB(OR)2 undergo ion-molecule
reactions to yield both addition products (by an implied radiative emi
ssion mechanism), ligand exchange, and proton transfer products, in bo
th positive and negative ion modes. Although an acidity for CH3B(OR)2
could not be determined, HOB(OR)2 has an acidity between acetaldehyde
and nitromethane. In light of the negligible polar electron acceptor p
roperties of the -B(OR)2 group, that functionality must therefore be o
ne of the best resonance electron acceptor groups known, almost half a
gain as effective as the nitro group.