Synthesis and structural characterization of (Z)-3-[(4-chlorophenylamino) methylene] naphthalene-2(3H)-one: An enol, keto or zwitterionic tautomer?

Venkatachalam, T. K., Pierens, Gregory K., Bernhardt, Paul V., Hammond, Luke and Reutens, David C. (2011) Synthesis and structural characterization of (Z)-3-[(4-chlorophenylamino) methylene] naphthalene-2(3H)-one: An enol, keto or zwitterionic tautomer?. Journal of Chemical Crystallography, 41 7: 944-951. doi:10.1007/s10870-011-0022-x


Author Venkatachalam, T. K.
Pierens, Gregory K.
Bernhardt, Paul V.
Hammond, Luke
Reutens, David C.
Title Synthesis and structural characterization of (Z)-3-[(4-chlorophenylamino) methylene] naphthalene-2(3H)-one: An enol, keto or zwitterionic tautomer?
Journal name Journal of Chemical Crystallography   Check publisher's open access policy
ISSN 1074-1542
1572-8854
Publication date 2011-07
Sub-type Article (original research)
DOI 10.1007/s10870-011-0022-x
Volume 41
Issue 7
Start page 944
End page 951
Total pages 8
Place of publication New York, NY, U.S.A.
Publisher Springer New York
Collection year 2012
Language eng
Formatted abstract
The structure of the title compound was determined using X-ray crystallography at both 173 and 293 K. The molecular structure and packing did not change significantly with temperature and a disordered structure was identified comprising a keto and enol tautomeric form. Analysis of the bond lengths in the vicinity of the C=O group suggested the keto form was predominantly in its zwitterionic form structure. 1H NMR spectroscopy showed the presence of a single compound in solution with two diagnostic doublets demonstrating the compound had an NH group next to a CH group resembling the zwitterionic form of the compound.
Keyword Synthesis
Schiff base
Nmr
X-ray
Crystallography
Keto-enol tautomer
Intramolecular hydrogen-bond
Nuclear magnetic resonance
Solid-State-NMR
Schiff-bases
Proton-transfer
Crystal-structure
C-13 NMR
N-salicylideneanilines
Absorption-spectra
Chemical-shifts
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

 
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