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Zeitschrift für Naturforschung A

A Journal of Physical Sciences

Editor-in-Chief: Holthaus, Martin

Editorial Board: Fetecau, Corina / Kiefer, Claus


IMPACT FACTOR 2017: 1.414

CiteScore 2018: 1.15

SCImago Journal Rank (SJR) 2018: 0.370
Source Normalized Impact per Paper (SNIP) 2018: 0.431

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1865-7109
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Volume 61, Issue 10-11

Issues

Synthetic and 1H and 13C NMRSpectral Studies on N-(Mono-substitutedphenyl)- acetamides and Substituted Acetamides, 2/3/4-YC6H4NH-COCH3–iXi (Y = CH3, F, Cl, Br, NO2; X = Cl, CH3; i = 0, 1, 2, 3)

Basavalinganadoddy Thimme Gowda
  • Department of Post-Graduate Studies and Research in Chemistry, Mangalore University, Mangalagangotri-574 199, Mangalore, India
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/ Shilpa Lakshmipathy
  • Department of Post-Graduate Studies and Research in Chemistry, Mangalore University, Mangalagangotri-574 199, Mangalore, India
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/ Jayalakshmi K. Lakshmipathy
  • Department of Post-Graduate Studies and Research in Chemistry, Mangalore University, Mangalagangotri-574 199, Mangalore, India
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Published Online: 2014-06-02 | DOI: https://doi.org/10.1515/zna-2006-10-1113

Nineteen N-(2/3/4-methyl/halo/nitro-phenyl)-acetamides and substituted acetamides, 2/3/4- YC6H4NH-CO-CH3iXi (Y = CH3, F, Cl, Br or NO2; X = Cl or CH3 and i = 0, 1, 2 or 3), have been prepared, characterized, and their 1H and 13C NMR spectra in solution measured and correlated. 1H and 13C NMR chemical shifts were assigned to the protons and carbon atoms, respectively, in line with those for similar compounds. Since the chemical shifts are dependent on the electron density around the nucleus or associated with the atom to which it is bound, the incremental shifts of the aromatic protons or carbon atoms due to -NH-CO-CH3iXi and -CO-CH3−iXi (X = Cl or CH3 and i = 0, 1, 2, 3) in all the N-phenyl-substituted acetamides, C6H5NH-CO-CH3−iXi, are calculated by comparing the proton or carbon chemical shifts of these compounds with those of benzene or aniline. The incremental shifts due to the groups in the parent compounds have also been computed by comparing the chemical shifts of the protons or carbon atoms in these compounds with those of benzene or aniline, respectively. The computed incremental shifts and other data were used to calculate the 1H and 13C NMR chemical shifts of the substituted compounds in three different ways. The calculated chemical shifts by the three methods compared well with each other and with the observed chemical shifts, testing the validity of the principle of additivity of the substituent effects in these compounds. The variation of 1H NMR chemical shifts of either the aromatic or N-H protons, with the substituents in N-(phenyl)- and N-(2/3/4-chloro/methylphenyl)-acetamides and substituted acetamides did not follow the same trend, while the variation of the 13C NMR chemical shifts of C-1 and C=O carbon atoms and those of alkyl carbon atoms of these compounds followed more or less the same trend.

Keywords: 1H and 13C NMR Spectra; N-Aryl-acetamides; N-Aryl-substituted Acetamides

About the article

Received: 2006-07-19

Published Online: 2014-06-02

Published in Print: 2006-11-01


Citation Information: Zeitschrift für Naturforschung A, Volume 61, Issue 10-11, Pages 595–599, ISSN (Online) 1865-7109, ISSN (Print) 0932-0784, DOI: https://doi.org/10.1515/zna-2006-10-1113.

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© 1946 – 2014: Verlag der Zeitschrift für Naturforschung. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

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