10.1021/jo9022414.s001
Barbara Bankiewicz
Barbara
Bankiewicz
Sławomir Wojtulewski
Sławomir
Wojtulewski
Sławomir J. Grabowski
Sławomir J.
Grabowski
Intramolecular Double Proton Transfer from 2-Hydroxy-2-iminoacetic Acid to 2-Amino-2-oxoacetic Acid
American Chemical Society
2010
Different criteria
basis sets
Quantum Theory
acid
intramolecular proton transfer process
DFT calculations
Dunning type
NBO
Natural Bond Orbitals
Intramolecular Double Proton Transfer
intramolecular interactions
QTAIM
MP 2
bond
2010-03-05 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Intramolecular_Double_Proton_Transfer_from_2_Hydroxy_2_iminoacetic_Acid_to_2_Amino_2_oxoacetic_Acid/2786407
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.