Structural investigation on phenyl- and pyridin-2-ylamino(methylene)naphthalen-2(3H)-one. Substituent effects on the NMR chemical shifts

Venkatachalam, Taracad K., Pierens, Gregory K., Campitelli, Mary R. and Reutens, David C. (2010) Structural investigation on phenyl- and pyridin-2-ylamino(methylene)naphthalen-2(3H)-one. Substituent effects on the NMR chemical shifts. Magnetic Resonance in Chemistry, 48 8: 585-592. doi:10.1002/mrc.2626


Author Venkatachalam, Taracad K.
Pierens, Gregory K.
Campitelli, Mary R.
Reutens, David C.
Title Structural investigation on phenyl- and pyridin-2-ylamino(methylene)naphthalen-2(3H)-one. Substituent effects on the NMR chemical shifts
Journal name Magnetic Resonance in Chemistry   Check publisher's open access policy
ISSN 1097-458X
0749-1581
Publication date 2010-08
Sub-type Article (original research)
DOI 10.1002/mrc.2626
Volume 48
Issue 8
Start page 585
End page 592
Total pages 8
Place of publication Chichester, England
Publisher John Wiley & Sons
Collection year 2011
Language eng
Formatted abstract
Schiff bases bearing phenyl and pyridyl groups were synthesized by condensation of appropriate amines with 2- hydroxynaphthaldehyde. These Schiff bases were obtained as colored crystalline solids. The proton NMR spectra of these compounds showed a doublet for the NH protons indicating a keto tautomer for these Schiff bases. The pyridyl-substituted Schiff bases containing hydroxylmoiety were found to show themost downfield shift for the NH protons in DMSO solvent, and this was rationalized due to the formation of a six- and five-membered ring using hydrogen bonds for these two compounds. Correspondingly, the olefinic proton of the Schiff bases is also found to be a doublet due to coupling to the amine proton. These Schiff bases exhibited thermochromic properties. Detailed NMR spectral analysis for both the phenyl- and pyridyl-substituted Schiff bases is presented.
Copyright © 2010 John Wiley & Sons, Ltd.
Keyword Phenyl
Pyridyl
Substituent effects
Nmr Analysis
Chemical Shifts
Keto-enol Quilibria
Nuclear Magnetic Resonance
2 Hydroxynaphthaldehyde Schiff-bases
Solid-state
Crystal-structure
Absorption-spectra
Proton-transfer
Tautomerism
Complexes
Anils
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ
Additional Notes Article first published online: 15 JUN 2010

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2011 Collection
Centre for Advanced Imaging Publications
 
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Created: Sun, 08 Aug 2010, 00:02:55 EST