期刊论文详细信息
Química Nova
Modulating the electronic structure of amino acids: interaction of model lewis acids with anthranilic acid
Tareq Irshaidat1 
[1] ,Al-Hussein Bin Talal University Department of Chemistry Ma'an Jordan
关键词: amino acid;    anthranilic acid;    zwitterion;    hydrogen bond;    NBO;   
DOI  :  10.5935/0100-4042.20140246
来源: SciELO
PDF
【 摘 要 】

On the basis of theoretical B3LYP calculations, Yáñez and co-workers (J. Chem. Theory Comput. 2012, 8, 2293) illustrated that beryllium ions are capable of significantly modulating (changing) the electronic structures of imidazole. In this computational organic chemistry study, the interaction of this β-amino acid and five model Lewis acids (BeF1+, Be2+, AlF2(1+), AlF2+, and Al3+) were investigated. Several aspects were addressed: natural bond orbitals, including second order perturbation analysis of intra-molecular charge delocalization and the natural population analysis atomic charges; molecular geometries; selected infrared stretching frequencies (C-N, C-O, and N-H), and selected ¹H-NMR chemical shifts. The data illustrate that this interaction can weaken the H-O bond and goes beyond strengthening the intra-molecular hydrogen bond (N...H-O) to cause a spontaneous transfer of the proton to the nitrogen atom in five cases generating zwitterion structures. Many new features are observed. Most importantly, the zwitterion structures include a stabilizing hydrogen bond (N-H...O) that varies in relative strength according to the Lewis acid. These findings explain the experimental observations of α-amino acids (for example: J. Am. Chem. Soc. 2001, 123, 3577) and are the first reported fundamental electronic structure characterization of β-amino acids in zwitterion form.

【 授权许可】

CC BY-NC   
 All the contents of this journal, except where otherwise noted, is licensed under a Creative Commons Attribution License

【 预 览 】
附件列表
Files Size Format View
RO202103040064635ZK.pdf 385KB PDF download
  文献评价指标  
  下载次数:9次 浏览次数:9次