Web Release Date: June 27,
A Computational Investigation of the Geometrical Structure and Protodeboronation of Boroglycine, H2N-CH2-B(OH)2
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Department of Chemistry, Bloomsburg University of Pennsylvania, Bloomsburg, Pennsylvania 17815, Department of Chemistry and Biochemistry, School of Science and Health, Philadelphia University, School House Lane and Henry Avenue, Philadelphia, Pennsylvania 19144, The Institute for Cancer Research, Fox Chase Cancer Center, 333 Cottman Avenue, Philadelphia, Pennsylvania 19111, The National Institutes of Health, National Heart, Lung, and Blood Institute, Building 50, Bethesda, Maryland 20851, Department of Biochemistry, Tufts University School of Medicine, 136 Harrison Avenue, Boston, Massachusetts 02111, and Department of Chemistry, Widener University, Chester, Pennsylvania 19013
Received: January 4, 2007
In Final Form: April 16, 2007
Abstract:
In this article the geometrical structure of the simple, achiral, 
-amino boronic acid boroglycine, H2N-CH2-B(OH)2, was investigated using density functional theory (DFT), second-order M
ller-Plesset (MP2)
perturbation theory, and coupled cluster methodology with single- and double-excitations (CCSD); the effects
of an aqueous environment were incorporated into the results by using a few explicit water molecules and/or
self-consistent reaction field (SCRF) calculations with the IEF polarizable continuum model (PCM). Neutral
reaction mechanisms were investigated for the direct protodeboronation (hydrolysis) of boroglycine (H2O +
H2N-CH2-B(OH)2 
B(OH)3 + H2N-CH3), for which 
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 (H2N-CH2-B(OH)2 H3C-NH-B(OH)2), for which the corresponding value of 
was -18.2 kcal/mol. A boron-oxygen double-bonded intermediate was found to play an important role in the 1,2-rearrangement mechanism.
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