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The statistical generation of SCS values and interaction factors for the13C NMR spectra of arenes

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Abstract

A new methodology which statistically determines substituent chemical shifts (SCS) and interaction factors of adjacent groups for use in the3C NMR spectroscopy of arenes is described. From a data base of 15,255 signals we have computed several hundred of these“statistical” SCS values (SSCS values), and interaction factors for many common pairs of groups. Some interaction factors for 1,2,3-substitution are also reported. When these SSCS values and interaction factors are used to predict the signal position they are found to give a correlation coefficient of predicted verses observed values of 0.994 with a standard deviation of 1.5 ppm.

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References

  1. Formáček, V.; Desnoyer, L.; Kellerhals, H. P.; Keller, T.; Clerc, J. T.13 C Data Bank Vol. 1; Bruker Physik: Karlsruhe, Germany,1976.

    Google Scholar 

  2. Johson, L. F.; Janowski, W. C.Carbon-13 NMR Spectra; Wiley-Interscience: New York.

  3. Jardon, P. W.; Vickery, E. H.; Pahler, L. F.; Pourahmady, N.; Mains, G. J.; Eisenbraun, E. J.J. Org. Chem. 1984,49, 2130.

    Article  CAS  Google Scholar 

  4. Iverson, D. J.; Hunter, G.; Blount, J. F.; Damewood, J. R.; Mislow, K.J. Am. Chem. Soc. 1981,103, 6073.

    Article  CAS  Google Scholar 

  5. Mann, B. E.J. Chem. Soc., Dalton Trans.1973, 2012.

  6. Bodner, G. M.; Todd, L. J.Inorg. Chem. 1974,13, 360.

    CAS  Google Scholar 

  7. Federov, L. A.; Petroovskii, P. V.; Fedin, E. I.; Panosyan, G. A.; Tsoi, A. A.; Baranetskaya, N. K.; Setkina, V. N.J. Organometal. Chem. 1979,182, 499.

    Google Scholar 

  8. Jackson, W. R.; Rae, I. D.; Wong, M. G.Aust. J. Chem. 1984,37, 1563.

    CAS  Google Scholar 

  9. Jackson, W. R.; Pincombe, C. F.; Rae, I. D.; Thapebinkarn, S.ibid. 1975,28, 1535.

    CAS  Google Scholar 

  10. Downton, P. A.; Mailvaganam, B.; Frampton, C. S.; Sayer, B. G.; McGlinchey, M. J.J. Am. Chem. Soc. 1990,112, 27.

    Article  CAS  Google Scholar 

  11. This paper.

  12. Dalling, D. K.; Ladner, K. H.; Grant, D. M.; Wollfenden, W. R.J. Am. Chem. Soc. 1977,99, 7142.

    Article  CAS  Google Scholar 

  13. Smith, W. B.; Deavenport, D. L.J. Mag. Reson. 1972,7, 364.

    CAS  Google Scholar 

  14. Proulx, T. W.; Smith, W. B.ibid. 1976,23, 477.

    CAS  Google Scholar 

  15. Kitching, W.; Praeger, D.; Moore, C. J.; Doddrell, D.; Adcock, W.J. Organometal. Chem. 1974,70, 339.

    Article  CAS  Google Scholar 

  16. Rizvl, S. Q. A.; Gupta, B. D.; Adcock, W.; Doddrell, D.; Kitching, W.ibid. 1973,63, 67.

    Google Scholar 

  17. Inamoto, N.; Masuda, S.; Tokumaru, K.; Tori, K.; Yoshida, M.; Yoshimura, Y.Tetrahedron Lett. 1976,41, 3707.

    Google Scholar 

  18. Ernst, L.Org. Magn. Reson. 1974,6, 540.

    Article  CAS  Google Scholar 

  19. Reynolds, W. F.; Peat, I. R.; Freedma, M. H.; Lyerla, J. R.Can. J. Chem. 1973,51, 1857.

    CAS  Google Scholar 

  20. Spiesecke, H.; Schneider, W. G.J. Chem. Phys. 1961,35, 731.

    CAS  Google Scholar 

  21. Berger, S.Tetrahedron 1976,32, 2451.

    Article  CAS  Google Scholar 

  22. Adcock, W.; Gupta, B. D.; Kitching, W.; Doddrell, D.; Geckel, M.J. Am. Chem. Soc. 1974,96, 7360.

    CAS  Google Scholar 

  23. Weissensteiner, W.; Schuster, I. I.; Blount, J. F.; Mislow, K.ibid. 1986,108, 6664.

    Article  CAS  Google Scholar 

  24. Chance, J. M.; Kahr, B.; Buda, A. B.; Toscano, J. P.; Mislow, K.J. Org. Chem. 1988,53, 3226.

    Article  CAS  Google Scholar 

  25. Acampora, M.; Ceccon, A.; Dal Farra, M.; Giacometti, G.; Rigatti, G.J. Chem. Soc., Perkin II1977, 483.

    Google Scholar 

  26. Senoff, C. V.; Ward, J. E. H.Inorg. Chem. 1975,14, 278.

    Article  CAS  Google Scholar 

  27. Shapiro, M. J.J. Org. Chem. 1978,43, 742.

    CAS  Google Scholar 

  28. Idem, ibid. 1977,42, 762.

    CAS  Google Scholar 

  29. Simonnin, M.-P.; Pouet, M.-J.; Terrier, F.J. Org. Chem. 1978,43, 855.

    Article  CAS  Google Scholar 

  30. Kitching, W.; de Jonge, I.; Adcock, W.; Abeywickrema, A. N.Org. Magn. Reson. 1980,14, 502.

    Article  CAS  Google Scholar 

  31. Sudmeijer, O.; Wilson, A. E.; Hays, G. R.ibid. 1984,22, 459.

    Article  CAS  Google Scholar 

  32. Bulbarela, A.; Tlahuext, H.; Morales, H. R.; Cuéllar, L.; Uribe, G.; Contreras, R.Magn. Reson. Chem. 1986,24, 1093.

    Article  CAS  Google Scholar 

  33. Shapiro, M. J.J. Org. Chem. 1978,43, 212.

    CAS  Google Scholar 

  34. Krabbenhoft, H. O. ibid.1978, 1830.

    CAS  Google Scholar 

  35. Takahashi, K.; Kondo, Y.; Asami, R.; Inoue, Y.Org. Magn. Reson. 1974,6, 580.

    CAS  Google Scholar 

  36. Schaeffer, C. D.; Zuckerman, J. J.; Yoder, C. H.J. Organometal. Chem. 1974,80, 29.

    Article  CAS  Google Scholar 

  37. Doddrell, D.; Lewis, K. G.; Mulquiney, C. E.; Adcock, W.; Kitching, W.; Bullpit, M.Aust. J. Chem. 1974,27, 417.

    CAS  Google Scholar 

  38. Doddrell, D.; Bullpit, M. L.; Moore, C. J.; Fong, C. W.; Kitchen, W.; Adcock, W.; Gupta, B. D.Tetrahedron Lett. 1973, 665.

  39. BudĚšínsky, M.; Exner, O.Magn. Reson. Chem. 1989,27, 585.

    Google Scholar 

  40. Olivato, P. R.; Rittner, R.ibid. 1992,30, 81.

    Article  CAS  Google Scholar 

  41. Newmark, R. A.; Hill, J. R.; Tiers, G. V. D.ibid. 1988,26, 612.

    Article  CAS  Google Scholar 

  42. Wnuk, S.; Wyrzykiewicz, E.; Kaczmarek, E.; Kinastowski, S.ibid. 1990,28, 271.

    Article  CAS  Google Scholar 

  43. Zeegers, P. J.; Thompson, M. J.ibid. 1992,30, 497.

    Article  CAS  Google Scholar 

  44. Kalinowski, H.-O.; Kessler, H.Org. Magn. Reson. 1975,7, 128.

    Article  CAS  Google Scholar 

  45. Dostovalova, V. I.; Federov, L. A.; Paasivirta, J.Magn. Reson. Chem. 1991,29, 830.

    Article  Google Scholar 

  46. Ewing, D. F.Org. Magn. Reson. 1979,12, 499.

    Article  CAS  Google Scholar 

  47. Zetta, L.; Gatti, G.ibid. 1972,4, 585.

    Article  CAS  Google Scholar 

  48. Coulson, D. R.J. Am. Chem. Soc. 1976,98, 3111.

    CAS  Google Scholar 

  49. Olah, G. A.; Grant, J. L.ibid. 1975,97, 1546.

    CAS  Google Scholar 

  50. Smith, W. B.; Prouix, T. W.Org. Magn. Reson. 1976,8, 567.

    CAS  Google Scholar 

  51. Bose, A. K.; Srinivasan, P. R.Tetrahedron 1975,31, 3025.

    Article  CAS  Google Scholar 

  52. Hearn, M. T. W.J. Magn. Reson. 1975,19, 401.

    CAS  Google Scholar 

  53. Nelson, G. L.; Levy, G. C.; Cargioli, J. D.J. Am. Chem. Soc. 1972,94, 3089.

    CAS  Google Scholar 

  54. Doddrell, D.; Barfield, M.; Adcock, W.; Aurangzeb, M.; Jordan, D.J. Chem. Soc., Perkin II1976, 409.

    Google Scholar 

  55. Hamer, G. K.; Peat, I. R.; Reynolds, W. F.Can. J. Chem. 1973,51, 897.

    CAS  Google Scholar 

  56. Jones, R. G.; Wilkins, J. M.Org. Magn. Reson. 1978,11, 20.

    Article  CAS  Google Scholar 

  57. Newmark, R. A.; Hill, J. R.ibid. 1977,9, 589.

    Article  CAS  Google Scholar 

  58. Wehrli, F. W.; de Haan, J. W.; Keulemans, A. I. M.; Exner, O.; Simon, W.Helv. Chim. Acta 1969,52, 103.

    CAS  Google Scholar 

  59. Dawson, D. A.; Reynolds, W. F.Can. J. Chem. 1975,53, 373.

    CAS  Google Scholar 

  60. Reynolds, W. F.; McClelland, R. A.ibid. 1977,55, 536.

    CAS  Google Scholar 

  61. Breitmaier, E.; Haas, G.; Voelter, W.Atlas of Carbon-13 NMR Data; Heyden: London, 1979.

    Google Scholar 

  62. Primary literature citations for aromatic compounds in this compendium are Lauterbur, P. C.J. Am. Chem. Soc. 1961,83, 1838;

    CAS  Google Scholar 

  63. The Atlas itself;

  64. Alger, T. D.; Grant, D. M.; Paul, E. G.J. Am. Chem. Soc. 1966,88, 5397;

    Article  CAS  Google Scholar 

  65. D. Lauer, Motell, E. L.; Traficante, D. D.; Maciel, G. E.ibid. 1972,94, 5335;

    Article  CAS  Google Scholar 

  66. Dhami, K. S.; Strothers, J. B.Can. J. Chem. 1965,43, 510;

    CAS  Google Scholar 

  67. Spiesecke, H.; Schneider, W. G.J. Phys. Chem. 1961,35, 731;

    CAS  Google Scholar 

  68. Tarpley, A. R.; Goldstein, J. H.ibid. 1972,76, 515;

    Article  CAS  Google Scholar 

  69. Dhami, K. S.; Strothers, J. B.Can. J. Chem. 1965,43, 479;

    CAS  Google Scholar 

  70. Idem, ibid. 1967,45, 233;

    CAS  Google Scholar 

  71. Buchanan, G. W.; Montaudo, G.; Finocchiard, P.Can. J. Chem. 1974,52, 3196;

    CAS  Google Scholar 

  72. Radeglia, R.; Jackowski, K.; Jessen, H.-J.Z. Chem. 1975,15, 311;

    CAS  Google Scholar 

  73. Voelter, W.; Fuchs, S.; Seuffer, R. H.; Zech, K.Monatsh. Chem. 1974,105, 1110;

    CAS  Google Scholar 

  74. Buchanan, G. W.; Montaudo, G.; Finocchiard, P.Can. J. Chem. 1974,52, 767;

    CAS  Google Scholar 

  75. Hawkes, G. E.; Herwig, K.; Roberts, J. D.J. Org. Chem. 1974,39, 1017;

    CAS  Google Scholar 

  76. Junghans, P.; Sprinz, H.Z. Chem. 1975,15, 153;

    CAS  Google Scholar 

  77. Hollstein, U.; Breitmaier, E.; Jung, G.J. Am. Chem. Soc. 1974,96, 8036;

    Article  CAS  Google Scholar 

  78. Ewers, U.; Guenther, H.; Jaenicke, L.Chem. Ber. 1973,106, 3951;

    CAS  Google Scholar 

  79. Buchanan, G. W.; Reyes-Zamora, G.; Clark, D. E.Can. J. Chem. 1974,52, 3895;

    CAS  Google Scholar 

  80. Hunter, D. H.; Strothers, J. B.ibid. 1973,51, 2884.

    CAS  Google Scholar 

  81. Hamer, G. K.; Peat, I. R.; Reynolds, W. F.Can. J. Chem. 1973,51, 915.

    CAS  Google Scholar 

  82. Dana, G.; Convert, O.; Girault, J.-P.; Mulliez, E.ibid. 1976,54, 1827.

    CAS  Google Scholar 

  83. Sol'aniová, E.; Toma, S.; Gronowitz, S.Org. Magn. Reson. 1976,8, 439.

    Google Scholar 

  84. Adcock, W.; Kitching, W.; Alberts, V.; Wickham, G.; Barron, P.; Doddrell, D.ibid. 1977,10, 47.

    Article  CAS  Google Scholar 

  85. Gronowitz, S.; Johnson, L.; Maholanyiova, A.; Toma, S.; Solcániová, E.ibid. 1975,7, 372.

    Article  CAS  Google Scholar 

  86. Levy, G. C.; White, D. M.; Cargoli, J. D.J. Magn. Reson. 1972,8, 280.

    CAS  Google Scholar 

  87. Buchanan, G. W.; Dawson, B. A.Can. J. Chem. 1975,54, 790.

    Google Scholar 

  88. Lynch, B. M.ibid. 1977,55, 541.

    CAS  Google Scholar 

  89. Leibfritz, D.Chem. Ber. 1975,108, 3014.

    CAS  Google Scholar 

  90. Inamoto, N.; Kushida, K.; Masuda, S.; Ohta, H.; Satoh, S.; Tamura, Y.; Tokumoru, K.; Tori, K.; Yoshida, M.Tetrahedron Lett. 1974, 3617.

  91. Shapiro, M. J.Tetrahedron 1977,33, 1091.

    Article  CAS  Google Scholar 

  92. Hansen, P. E.; Poulsen, O. K.; Berg, A.Org. Magn. Reson. 1977,9, 649.

    Article  CAS  Google Scholar 

  93. FrØyen, P.; Morris, D. G.Acta Chem. Scand. B 1976,30, 435.

    Google Scholar 

  94. Scott, K. N.J. Am. Chem. Soc. 1972,94, 8564.

    CAS  Google Scholar 

  95. Matsubayashi, G.; Tanaka, T.Spectrochim. Acta 1974,30A, 869.

    CAS  Google Scholar 

  96. Schaeffer, C. D.; Zuckerman, J. J.J. Organometal. Chem. 1973,55, 97.

    Article  CAS  Google Scholar 

  97. Radeglia, R.; Storek, W.; Engelhardt, G.; Ritschl, F.; Lippmaa, E.; Pehk, T.; Mägi, M.; Martin, D.Org. Magn. Reson. 1973,5, 419.

    Article  CAS  Google Scholar 

  98. Newmark, R. A.; Hill, J. R.J. Magn. Reson. 1976,21, 1.

    CAS  Google Scholar 

  99. Buchanan, G. W.; Montaudo, G.; Finocchiaro, P.Can. J. Chem. 1974,52, 767.

    CAS  Google Scholar 

  100. Stephany, R. W.; de Bie M. J. A.; Drenth, W.Org. Magn. Reson. 1974,6, 45.

    Article  CAS  Google Scholar 

  101. Buchanan, G. W.; Reyes-Zamora, C.; Clarke, D. E.Can. J. Chem. 1974,52, 3895.

    CAS  Google Scholar 

  102. Wilson, N. K.; Zehr, R. D.; Ellis, P. D.J. Magn. Reson. 1976,21, 437.

    CAS  Google Scholar 

  103. Lepoivre, I. A.; Dommisse, R. A.; Alderweireldt, F. C.Org. Magn. Reson. 1975,7, 422.

    Article  CAS  Google Scholar 

  104. Kalinowski, H.-O.; Kessler, H.ibid. 1974,6, 305.

    Article  CAS  Google Scholar 

  105. Fivolt, F. J.; Sojka, S. A.; Wolfe, R. A.J. Org. Chem. 1982,47, 148.

    Google Scholar 

  106. Kresze, G.; Berger, M.; Claus, P. K.; Rieder, W.Org. Magn. Reson. 1976,8, 170.

    Article  CAS  Google Scholar 

  107. Schraml, J.; Chvalovský, V.; Jancke, H.; Engelhardt, G.ibid. 1977,9, 237.

    Article  CAS  Google Scholar 

  108. Ernst, L.Tetrahedron Lett. 1974,35, 3079.

    Google Scholar 

  109. Schraml, J.; Chvalovský, V.; Mägi, M.; Lippmaa, E.; Calas, R.; Dunoguès, J.; Bourgeois, P.;J. Organometal. Chem. 1976,120, 41.

    Article  CAS  Google Scholar 

  110. Ernst, L.Org. Magn. Reson. 1977,9, 35.

    Article  CAS  Google Scholar 

  111. Bullpitt, M.; Kitching, W.; Adcock, W.; Doddrell, D.J. Organometal. Chem. 1976,116, 161.

    CAS  Google Scholar 

  112. Idem, ibid. 1976,116, 187.

    CAS  Google Scholar 

  113. Netzel, D. A.Org. Magn. Reson. 1978,11, 58.

    Article  CAS  Google Scholar 

  114. Calvert, D.; de La Mare P. B. D.; Isaacs, N. S.J. Chem. Res (S)1978, 156, (M)1978, 2001–2037.

    Google Scholar 

  115. Jones, R. G.; Partington, P.J. Chem. Soc., Faraday Trans. 1972,68, 2087.

    CAS  Google Scholar 

  116. Kalinowski, H.-O.; Berger, S.; Braun, S.13 C-NMR Spektroskopie; Verlag Chemie: New York, 1984.

    Google Scholar 

  117. Ilczyszyn, M.; Latajka, Z.; Ratajczak, H.Org. Magn. Reson. 1980,13, 132.

    Article  Google Scholar 

  118. Sterk, H.; Fabian, W.Ibid. 1975,7, 274.

    Article  CAS  Google Scholar 

  119. Belstel, D. W.; Edwards, W. D.J. Phys. Chem. 1976,80, 2023.

    Google Scholar 

  120. Kosugi, Y.; Furuya, Y.Tetrahedron 1980,36, 2741.

    Article  CAS  Google Scholar 

  121. Edlund, U.; Norström, A.Org. Magn. Reson. 1977,9, 196.

    CAS  Google Scholar 

  122. Jha, H. C.; Zilliken, F.; Offermann, W.; Breitmaier, F.Can. J. Chem. 1981,59, 2266.

    CAS  Google Scholar 

  123. Mullen, G. P.; Luthra, N. P.; Dunlap, R. B.; Odom, J. D.J. Org. Chem. 1985,50, 811.

    CAS  Google Scholar 

  124. Kusuyama, Y.; Dyllick-Brenzinger, C.; Roberst, J. D.Org. Magn. Reson. 1980,13, 372.

    Article  CAS  Google Scholar 

  125. Abraham, R. J.; Wileman, D. F.; Bedford, G. R.; Greatbanks, D.J. Chem. Soc., Perkin Trans. II1972, 1733.

    Google Scholar 

  126. Butler, R. N.; McEvoy, T. M.ibid. 1978, 1087.

    Google Scholar 

  127. Chrisope, D. R.; Keel, R. A.; Baumstark, A. L.; Boykin, D. W.J. Heterocycl. Chem. 1981,18, 795.

    CAS  Google Scholar 

  128. Bromilow, J.; Brownlee, R. T. C.; Craik, D. J.; Sadek, M.Mag. Reson. Chem. 1986,24, 862.

    CAS  Google Scholar 

  129. Klasinc, L.; Knop, J. V.; Meiners, H.-J.; Zeil, W.Z. Naturforsch 1972,27a, 1772.

    Google Scholar 

  130. Llabres, G.; Baiwir, M.; Christiaens, L.; Denoel, J.; Laitem, L.; Piette, J.-L.Can. J. Chem. 1978,56, 2008.

    CAS  Google Scholar 

  131. Briggs, J. M.; Randall, E. W.J. Chem. Soc., Perkin Trans. II1973, 1789.

    Google Scholar 

  132. Sopchik, A. E.; Kingsbury, C. A.J. Chem. Soc., Perkin Trans. II1979, 1058.

    Google Scholar 

  133. Newmark, R. A.; Hill, J. R.Org. Magn. Reson. 1980,13, 40.

    Article  CAS  Google Scholar 

  134. Agrawal, P. K.; Schneider, H. J.; Malik, M. S.; Rastogi, S. N.ibid. 1983,21, 146.

    CAS  Google Scholar 

  135. Miyajima, G.; Akiyama, H.; Nishimoto, K.ibid. 1972,4, 811.

    Article  CAS  Google Scholar 

  136. Hinton, J. F.; Layton, B.ibid. 1972,4, 353.

    Article  CAS  Google Scholar 

  137. Nakai, Y.; Yamada, F.ibid. 1978,11, 607.

    Article  CAS  Google Scholar 

  138. Dhami, K. S.; Strothers, J. B.Can. J. Chem. 1966,44, 2855.

    CAS  Google Scholar 

  139. Jones, A. J.; Grant, D. M.; Russell, J. G.; Fraenkel, G.J. Phys. Chem. 1969,73, 1624.

    CAS  Google Scholar 

  140. Adcock, W.; Gupta, B. D.; Khor, T. C.; Doddrell, D.; Jordan, D.; Kitching, W.J. Am. Chem. Soc. 1974,96, 1595.

    CAS  Google Scholar 

  141. Wong, C. W.; Lincoln, S. F.; Williams, E. H.Aust. J. Chem. 1978,31, 2623.

    Google Scholar 

  142. Idem, ibid. 1978,31, 2615.

    Google Scholar 

  143. Nakai, Y.; Takabayashi, T.; Yamada, F.Org. Magn. Reson. 1980,13, 95.

    Article  Google Scholar 

  144. Llinares, J.; Galy, J. P.; Faure, R.; Vincent, E. J.; Elguero, J.Can. J. Chem. 1979,57, 937.

    CAS  Google Scholar 

  145. Pretsch, E.; Fürst, A.; Robien, W.Anal. Chim. Acta 1991,248, 415 and references therein.

    Article  CAS  Google Scholar 

  146. Mahaffy, C. A. L.; Nanney, J. R.J. Fluorine Chem. 1994,67, 67;

    CAS  Google Scholar 

  147. Nanney, J. R.; Mahaffy, C. A. L.ibid. 1994,68, 181.

    CAS  Google Scholar 

  148. Pouchert, C. J.; Behnke, J.The Aldrich Library of 13 C and 1 H FT NMR Spectra, Edition 1; The Aldrich Chemical Company: Wisconsin, 1993.

    Google Scholar 

  149. Nanney, J. R.; Traylor, A. K.; Mahaffy, C. A. L.J. Fluorine Chem. 1993,64, 217.

    CAS  Google Scholar 

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  1. Department of Mathematics, Auburn Univerity at Montgomery, Montgomery, Alabama

    R. E. Jetton & J. R. Nanney

  2. Department of Chemistry, Auburn University at Montgomery, 36117, Montgomery, Alabama

    C. A. L. Mahaffy & C. C. Price

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  1. R. E. Jetton
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Jetton, R.E., Nanney, J.R., Mahaffy, C.A.L. et al. The statistical generation of SCS values and interaction factors for the13C NMR spectra of arenes. Struct Chem 6, 301–315 (1995). https://doi.org/10.1007/BF02293124

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