Structural studies on Mannich bases of 2-Hydroxy-3,4,5,6-tetrachlorobenzene. An UV, IR, NMR and DFT study. A mini-review

Mannich bases of 2-Hydroxy-3,4,5,6-tetrachlorobenzene are chosen as an exemplary case for tautomeric Mannich bases. Molecular structures are calculated. OH stretching frequencies are rationalized based on DFT calculations. Intrinsic deuterium isotope effects on 13C chemical shifts in the M-form are...

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Bibliographic Details
Published inJournal of molecular structure Vol. 1119; pp. 235 - 239
Main Authors Hansen, Poul Erik, Spanget-Larsen, Jens
Format Journal Article
LanguageEnglish
Published Elsevier B.V 05.09.2016
Subjects
Ambient temperature
Chemical bonds
Deuterium
DFT calculations
Isotope effect
Mannich bases
Mathematical analysis
Molecular structure
Nuclear magnetic resonance
OH stretching frequency predictions
pKa differences
Stretching
Tautomerism
pKa differences
OH stretching frequency predictions
Tautomerism
Mannich bases
DFT calculations
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Summary:Mannich bases of 2-Hydroxy-3,4,5,6-tetrachlorobenzene are chosen as an exemplary case for tautomeric Mannich bases. Molecular structures are calculated. OH stretching frequencies are rationalized based on DFT calculations. Intrinsic deuterium isotope effects on 13C chemical shifts in the M-form are estimated based on OH bond lengths. The observed deuterium isotope effects on 13C chemical shifts are demonstrated to be largely of equilibrium type except at ambient temperatures. [Display omitted] •Prediction of OH stretching frequencies based on simple DFT calculations.•Deuterium isotope effects on 13C chemical shifts to reveal tautomerism.•Prediction of isotope effects based on calculated OH bond lengths.
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ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2016.04.075