Evidence of first-order alkyl-ring proton coupling is reported for the 4-alkylnitrobenzenes. Typical coupling constants of 0.7 Hz and 0.3 Hz were found for α-alkyl coupling with the ortho and meta ring protons, respectively, when the alkyl function was methyl, ethyl, and isopropyl. No β-alkyl coupling with ring protons was observed for the ethyl, isopropyl, or t -butyl groups, suggesting that the magnitude of the coupling constant is vanishingly small.
D. W. Beistel and H. Chen, "PMR Spectra Of The 4-alkylnitrobenzenes," The Journal of Chemical Physics, vol. 59, no. 9, pp. 4648 - 4651, American Institute of Physics, Jan 1973.
The definitive version is available at https://doi.org/10.1063/1.1680675
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01 Jan 1973