• C Gnanasekaran

      Articles written in Journal of Chemical Sciences

    • Reaction of ethyl bromoacetate with substituted naphthoate ions

      K Rajasekaran C Gnanasekaran

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      Rate constants for the reaction of ethyl bromoacetate with three series of substituted naphthoate ions have been measured in an acetone-water mixture (90% v/v). Using σp values rate constants at 30o correlate well with the Hammett equation yielding ρ=−0.54, −0.19 and −0.25 for (4,1−), (6,1−) and (6,2−) series, respectively. Comparison of these ρ values with those of the reaction of phenacyl bromide reveals the failure of the reactivity-selectivity principle RSP in these reactions. Failure of RSP has been explained in terms of isoselective temperature.

    • Substituent effects on carbon-13 NMR chemical shifts of side chain carbonyl carbons of 4-substituted 1-naphthamides

      K Rajasekaran C Gnanasekaran T C Wong

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      Substituent induced13C NMR chemical shifts of side chain carbonyl carbons of several 4-substituted 1-naphthamides have been measured in DMSO-d6 solvent. Analysis of the substituent induced chemical shifts by the DSP equation gave the regression equation. Both {ie207-1} and {ie207-2} values were negative. The negative sign on {ie207-3} term indicates the operation of a reverse substituent effect and that π-polarisation is the important mechanism for the transmission of substituent effects by inductive effect. Theperi-hydrogen interaction in naphthamides forces the amide group out of the plane of the naphthalene ring.

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