Vibrational Spectroscopy of N-Methyliminodiacetic Acid (MIDA)-Protected Boronate Ester: Examination of the B-N Dative Bond

被引：15

作者：

Reinemann, Dana N. ^{[1
]}

Wright, Ashley M. ^{[1
]}

Wolfe, Jonathan D. ^{[1
]}

Tschumper, Gregory S. ^{[1
]}

Hammer, Nathan I. ^{[1
]}

机构：

[1] Univ Mississippi, Dept Chem & Biochem, University, MS 38677 USA

来源：

JOURNAL OF PHYSICAL CHEMISTRY A | 2011年 / 115卷 / 24期

基金：

美国国家科学基金会;

关键词：

AMMONIA-BORANE; DENSITY FUNCTIONALS; NEUTRON-SCATTERING; CRYSTAL-STRUCTURE; DIHYDROGEN BOND; FORCE-CONSTANTS; RAMAN-SPECTRA; COMPLEX; BH3NH3; B3LYP;

D O I：

10.1021/jp112016j

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

N-Methyliminodiacetic acid (MIDA)-protected boronate esters are a new class of reagents that offer great promise in iterative Suzuki-Miyaura cross-coupling reactions. Compared to earlier reagents, MIDA esters are easily handled and are benchtop stable under air indefinitely. The success of this new species is tied to its unique molecular architecture. Compared to the simpler B-N containing molecules ammonia borane and trimethylamine borane, MIDA esters are much larger, and the sp(3) hybridized boron atom is secured by two five membered rings, making this molecular class stable for spectroscopic study. Here, we present infrared, Raman, and surface enhanced Raman (SERS) spectra of methylboronic acid MIDA ester. Comparisons of the spectroscopic results to those from electronic structure calculations suggest that the B-N stretching mode in this molecule lies in the range 560-650 cm(-1), making it among the lowest energy vibrations observed to date that can be primarily attributed to B-N stretching.

引用

页码：6426 / 6431

页数：6

共 26 条

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[23] Studies on proline boronic acid dipeptide inhibitors of dipeptidyl peptidase tv. Identification of a cyclic species containing a B-N bond
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[25] Tests of the MP2 model and various DFT models in predicting the structures and B-N bond dissociation energies of amine-boranes (X3C)mH3-mB-H(CH3)nH3-n (X = H, F; m=0-3; n=0-3):: Poor preformance of the B3LYP approach for dative B-N bonds
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