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• W2088049476 abstract "Carbon-13 chemical shifts are reported for 16 para-substituted phenyl isothiocyanates measured at 1 and 10 mol % in chloroform-d solution. Data for the NCS group were not obtained at 1 mol %, but concentration effects for the other resonances were negligible. Hammett, dual substituent parameter (DSP) and DSP-nonlinear resonance (DSP-NLR) analyses were used to evaluate substituent effects on the substituent chemical shifts (SCS) for the ipso-carbon (C-1), C-2, and the NCS carbon atoms. A good Hammett correlation was observed for C-1 (νp+ = 8.1 ppm, r = 0.98 at 1 mol %) but was improved for the higher order correlations with the following results, DSP:ρ I = 5.4, ρR° = 22.2, r = 0.998; DSP-NLR: ρI = 5.6, ρR° = 20.5, ϵ = −0.22, r = 0.999. The 10 mol % data were very similar except the value of ϵ was −0.26 and confirms the phenyl-bonded NCS moiety as a mild electron acceptor substituent. Hammett correlations were unsuccessful for the C-2 data, but fairly good results were obtained from the higher order analyses. For the 1 mol % data, DSP: νI = 1.6, νR° = −2.0, r = 0.976; DSP-NLR: νI = 1.8, νR° = −2.6, ϵ = 1.1, r = 0.982. Excellent correlations were obtained for the 10 mol % NCS carbon data. Hammett: νp° = 6.2, r = 0.997; DSP: νI = 5.9, νR° = 7.0, r = 0.997; DSP-NLR: νI = 5.8, νR° = 7.6, ϵ = 0.25, r = 0.997. The positive ν values in these three correlations contrast the negative values usually observed for carbonyl and thiocarbonyl carbons, and more closely parallel results previously reported for the β-carbon of styrenes and benzylidene anilines with para-substituents in the aniline ring." @default.
• W2088049476 created "2016-06-24" @default.
• W2088049476 creator A5065337041 @default.
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• W2088049476 date "1982-08-01" @default.
• W2088049476 modified "2023-09-25" @default.
• W2088049476 title "Carbon-13 NMR spectra of a series ofpara-substituted phenyl isothiocyanates. Linear free energy relationships for carbon-13 substituent chemical shifts" @default.
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• W2088049476 doi "https://doi.org/10.1002/mrc.1270190408" @default.
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