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Sulfur-33 Nuclear Magnetic Resonance Spectra of Substituted Benzenesulfonic Acids in Relation to Non-Additivity of Carbon-13 Chemical Shifts

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Abstract

The sulfur-33 nuclear magnetic resonance (NMR) spectra of thirteen kinds of benzenesulfonates have been obtained. Their chemical shifts varied qualitatively with the substitutent parameters. The spectral line width relative to that of benzenesulfonate reflects a change in the spherical configuration around the sulfur atom, which is related to a chemical shift deviation from the additivity calculation for carbon-13 NMR. Substitution with SO3- or CO1-does not change the line width, in spite of a large deviation of the carbon-13 NMR chemical shifts, the cause has been deduced as being interactions between negatively charged substituents. Quinoid structures distort the spherically more symmetrical configuration of the SO3- group, resulting in an extremely large broadening of the spectra of sodium salts of para- and meta-phenolsulfonic acids. The spectrum of the former is not observed with accumulation for three days.

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References

  1. T. C. Farrar, B. M. Trost, S. L. Tang and S. E. Springer-Wilson, J. Am. Chem. Soc., 107, 262 (1985).

    Article  CAS  Google Scholar 

  2. R. Faure, E. J. Vincent, J. M. Ruiz and L. Lena, Org. Magn. Reson., 15, 401 (1981).

    Article  CAS  Google Scholar 

  3. Y. Kosugi, Yukagaku, to be published (1989).

  4. P. Fabian, Adv. Space Res., 1, 17 (1981).

    Article  CAS  Google Scholar 

  5. T. Noy, P. Fabian, R. Borchers, F. Janssen, C. Cramers and J. Rijks, J. Chromatogr., 393, 343 (1987).

    Article  CAS  Google Scholar 

  6. R. E. Wasylishen, C. Connor, and J. O. Friedrich, Can. J. Chem., 62, 981 (1984).

    Article  CAS  Google Scholar 

  7. Y. Kosugi, Anal. Sci., 4, 353 (1988).

    Article  CAS  Google Scholar 

  8. Y. Kosugi and Y. Furuya, Tetrahedron, 36, 2741 (1980).

    Article  CAS  Google Scholar 

  9. Ortho-effect will be published elsewhere.

  10. J. Bromilow, R. T. C. Brownlee, D. J. Craik, M. Sadek and R. W. Taft, J. Org. Chem., 45, 2429 (1980).

    Article  CAS  Google Scholar 

  11. J. Bromilow, R. T. C. Brownlee, D. J. Craik and M. Sedek, Magn. Reson. Chem., 24, 862 (1986).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Synthetic Chemistry, Faculty of Engineering, Nagoya University, Nagoya, 464, Japan

    Yoshio Kosugi

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  1. Yoshio Kosugi
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Kosugi, Y. Sulfur-33 Nuclear Magnetic Resonance Spectra of Substituted Benzenesulfonic Acids in Relation to Non-Additivity of Carbon-13 Chemical Shifts. ANAL. SCI. 5, 253–255 (1989). https://doi.org/10.2116/analsci.5.253

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  • DOI: https://doi.org/10.2116/analsci.5.253

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