Institute of Chemistry, University of Białystok, ul. Hurtowa 1, 15-399 Białystok, Poland.
J Org Chem. 2010 Mar 5;75(5):1419-26. doi: 10.1021/jo9022414.
The double intramolecular proton transfer process which transforms 2-hydroxy-2-iminoacetic acid into 2-amino-2-oxoacetic acid is analyzed. The MP2 and DFT calculations were performed for different tautomers and conformers of these species. Pople style (6-311++G(d,p), 6-311++G(3df,3pd)) and Dunning type (aug-cc-pVTZ) basis sets were applied. O-H...O, N-H...O, and O-H...N intramolecular hydrogen bonds were also analyzed with the use of Quantum Theory of "Atoms in Molecules" (QTAIM) as well as Natural Bond Orbitals (NBO) method. Different criteria of the hydrogen bonding existence were applied here for intramolecular interactions. It was found that some of N-H...O hydrogen bonds may be treated as blue-shifting ones.
对将 2-羟基-2-亚氨基乙酸转化为 2-氨基-2-氧代乙酸的双分子质子转移过程进行了分析。针对这些物质的不同互变异构体和构象，进行了 MP2 和 DFT 计算。应用了 Pople 风格（6-311++G(d,p)，6-311++G(3df,3pd)）和 Dunning 类型（aug-cc-pVTZ）基组。还使用分子中的原子量子理论（QTAIM）以及自然键轨道（NBO）方法分析了 O-H...O、N-H...O 和 O-H...N 分子内氢键。这里针对分子内相互作用应用了不同的氢键存在标准。结果发现，某些 N-H...O 氢键可以被视为蓝移氢键。
