In this article the geometrical structure of the simple, achiral,
![](/images/gifchars/alpha.gif)
-amino boronic acid boroglycine, H
2N-CH
2-B(OH)
2, was investigated using density functional theory (DFT), second-order M
![](/images/entities/oslash.gif)
ller-Plesset (MP2)perturbation theory, and coupled cluster methodology with single- and double-excitations (CCSD); the effectsof an aqueous environment were incorporated into the results by using a few explicit water molecules and/orself-consistent reaction field (SCRF) calculations with the IEF polarizable continuum model (PCM). Neutralreaction mechanisms were investigated for the direct protodeboronation (hydrolysis) of boroglycine (H
2O +H
2N-CH
2-B(OH)
2 ![](/images/entities/rarr.gif)
B(OH)
3 + H
2N-CH
3), for which
![](/isubscribe/journals/jpcafh/111/i28/eqn/jp0700682<font color=)
e10001.gif"> was -21.9 kcal/mol at the MP2(FC)/aug-cc-pVDZ level, and for the 1,2-carbon-to-nitrogen shift of the -B(OH)
2 moiety (H
2N-CH
2-B(OH)
2 ![](/images/entities/rarr.gif)
H
3C-NH-B(OH)
2), for which the corresponding value of
![](/isubscribe/journals/jpcafh/111/i28/eqn/jp0700682<font color=)
e10002.gif"> was -18.2 kcal/mol. A boron-oxygen double-bonded intermediate was found to play an important role in the 1,2-rearrangement mechanism.