Heteronuclear NMR spectroscopic investigations of hydrogen bonding in 2-(benzo[d]thiazole-2'-yl)-N-alkylanilines

Venkatachalam, T. K., Pierens, G. K., Bernhardt, P. V. and Reutens, D. C. (2015) Heteronuclear NMR spectroscopic investigations of hydrogen bonding in 2-(benzo[d]thiazole-2'-yl)-N-alkylanilines. Magnetic Resonance in Chemistry, 53 6: 448-453. doi:10.1002/mrc.4228

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Author Venkatachalam, T. K.
Pierens, G. K.
Bernhardt, P. V.
Reutens, D. C.
Title Heteronuclear NMR spectroscopic investigations of hydrogen bonding in 2-(benzo[d]thiazole-2'-yl)-N-alkylanilines
Formatted title
Heteronuclear NMR spectroscopic investigations of hydrogen bonding in 2-(benzo[d]thiazole-2′-yl)-N-alkylanilines
Journal name Magnetic Resonance in Chemistry   Check publisher's open access policy
ISSN 0749-1581
1097-458X
Publication date 2015-04-09
Sub-type Article (original research)
DOI 10.1002/mrc.4228
Volume 53
Issue 6
Start page 448
End page 453
Total pages 6
Place of publication Chichester, West Sussex, United Kingdom
Publisher John Wiley & Sons
Collection year 2016
Language eng
Formatted abstract
The 2-(benzo[d]thiazole-2′-yl)-N-alkylanilines have previously revealed the presence of a strong intramolecular hydrogen bond. This in turn gives rise to a more complicated multiplet for the protons attached to the carbon adjacent to the amino group. This intramolecular hydrogen bond was investigated by a deuterium exchange experiment using heteronuclear NMR spectroscopy (1H, 13C, 15 N and 2H). We observed changes in the multiplet structure and chemical shifts providing further evidence that the deuterium replaces the hydrogen in the intramolecular hydrogen bond. A time course study of the D2O exchange confirmed the presence of a strong hydrogen bond. The comparison of the structures obtained by X-ray crystallography showed a very small difference in planarity between the two-substituted and four-substituted amino compounds. In both the cases, the phenyl ring is not absolutely coplanar with the thiazole unit. The existence of this intramolecular hydrogen bond in 2-(benzo[d]thiazole-2′-yl)-N-alkylanilines was further confirmed by single crystal X-ray crystallography.
Keyword NMR
Heteronuclear
Hydrogen hond
Deuterium
Hydrogen bond
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ
Additional Notes Article first published online: 9 APR 2015

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2016 Collection
School of Chemistry and Molecular Biosciences
Centre for Advanced Imaging Publications
 
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Created: Fri, 10 Apr 2015, 19:30:48 EST by Mrs Louise Nimwegen on behalf of Centre for Advanced Imaging