A comparative study between para-aminophenyl and ortho-aminophenyl benzothiazoles using NMR and DFT calculations

Pierens, G. K., Venkatachalam, T. K. and Reutens, D. (2014) A comparative study between para-aminophenyl and ortho-aminophenyl benzothiazoles using NMR and DFT calculations. Magnetic Resonance in Chemistry, 52 8: 453-459. doi:10.1002/mrc.4088

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Author Pierens, G. K.
Venkatachalam, T. K.
Reutens, D.
Title A comparative study between para-aminophenyl and ortho-aminophenyl benzothiazoles using NMR and DFT calculations
Formatted title
A comparative study between para-aminophenyl and ortho-aminophenyl benzothiazoles using NMR and DFT calculations
Journal name Magnetic Resonance in Chemistry   Check publisher's open access policy
ISSN 0749-1581
1097-458X
Publication date 2014-06-03
Year available 2014
Sub-type Article (original research)
DOI 10.1002/mrc.4088
Open Access Status File (Author Post-print)
Volume 52
Issue 8
Start page 453
End page 459
Total pages 7
Place of publication Chichester, West Sussex, United Kingdom
Publisher John Wiley & Sons
Collection year 2015
Language eng
Formatted abstract
Ortho-substituted and para-substituted aminophenyl benzothiazoles were synthesised and characterised using NMR spectroscopy. A comparison of the proton chemical shift values reveals significant differences in the observed chemical shift values for the NH protons indicating the presence of a hydrogen bond in all ortho-substituted compounds as compared to the para compounds. The presence of intramolecular hydrogen bond in the ortho amino substituted aminophenyl benzothiazole forces the molecule to be planar which may be an additional advantage in developing these compounds as Alzheimer's imaging agent because the binding to amyloid fibrils prefers planar compounds. The splitting pattern of the methylene proton next to the amino group also showed significant coupling to the amino proton consistent with the notion of the existence of slow exchange and hydrogen bond in the ortho-substituted compounds. This is further verified by density functional theory calculations which yielded a near planar low energy conformer for all the o-aminophenyl benzothiazoles and displayed a hydrogen bond from the amine proton to the nitrogen of the thiazole ring. A detailed analysis of the 1H, 13C and 15N NMR chemical shifts and density functional theory calculated structures of the compounds are described.
Keyword Aminophenyl benzothiazoles
Hydrogen bond
1H NMR
13C NMR
15N NMR
DFT calculations
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ
Additional Notes Article first published online: 3 JUN 2014

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2015 Collection
Centre for Advanced Imaging Publications
 
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Created: Thu, 12 Jun 2014, 15:48:51 EST by Sandrine Ducrot on behalf of Centre for Advanced Imaging