Advertisement

X=Y Bonds Other than Carbonyl vS=O, N=O, P=O, P=S, C=S and C=Se Vibrations

Chapter

Abstract

The SO bond in sulphoxides differs from the double bond of the carbonyl group in that it is made up of a strong σ S—O link strengthened by two relatively weak bonds at right angles to each other. These are formed through the overlap of the p orbitals of the oxygen atom with the d Orbitals of the sulphur. One result of this is that the oxygen atom, although polar, is rather less basic than would be expected, because the p character of the oxygen lone pair is reduced. This link also differs from the carbonyl group in that any double bonds attached to the sulphur atom do not lie in the SO plane, and conjugation effects are thereby much reduced. The vibrational frequencies of the SO link in various chemical environments are well characterized and are summarized in Table 6.1 (p. 200).

Keywords

Sulphur Atom Complex Molecule Thionyl Chloride Phosphine Oxide Conjugation Effect 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Bibliography

  1. 1.
    Cairns, Eglinton and Gibson, Spectrochim. Acta, 1964, 20, 31.Google Scholar
  2. 2.
    Cairns and Eglinton, Spectrochim. Acta, 1964, 20, 159.Google Scholar
  3. 3.
    Tamres and Searles, J. Amer. Chem. Soc., 1959, 81, 2100.Google Scholar
  4. 4.
    Gramstad, Spectrochim. Acta, 1963, 19, 829.Google Scholar
  5. 5.
    Otting and Neugebauer, Chem. Ber., 1962, 95, 540.Google Scholar
  6. 6.
    Foffani, Ghersetti and Montanori, Ric. Sci., 1960, 30, 1010.Google Scholar
  7. 7.
    Del La Mere, Milien, Tillett and Watson, J. Chem. Soc., 1963, 1619.Google Scholar
  8. 8.
    Pinchas, Samuel and Weiss Broday, J. Chem. Soc., 1962, 3968.Google Scholar
  9. 9.
    Ghersetti, Boll. Sci. Chim. Ind. Bologna, 1961, 19, 83.Google Scholar
  10. 10.
    Kresze, Ropte and Schrader, Spectrochim. Acta, 1965, 21, 1633.Google Scholar
  11. 11.
    Horrocks and Cotton, Spectrochim. Acta, 1961, 17, 134; 1960, 16, 358.Google Scholar
  12. 12.
    Ghersetti and Modena, Spectrochim. Acta, 1963, 19, 1809; Ann. Chim. Rome, 1963, 53, 1083.Google Scholar
  13. 13.
    Grisko and Gur’janova, J. Phys. Chem. Moscow, 1958, 32, 2725.Google Scholar
  14. 14.
    Detoni and Hadzi, Spectrochim. Acta, 1957, 14, 601.Google Scholar
  15. 15.
    Simon and Heintz, Chem. Ber., 1962, 95, 2333.Google Scholar
  16. 16.
    Glass and Pullin, Trans. Faraday Soc., 1961, 57, 546.Google Scholar
  17. 17.
    Kresze and Maschke, Chem. Ber., 1961, 94, 450.Google Scholar
  18. 18.
    Long and Bailey, Trans. Faraday Soc., 1963, 59, 792.Google Scholar
  19. 19.
    Gillespie and Robinson, Can. J. Chem., 1961, 39, 2171.Google Scholar
  20. 20.
    Daasch, Spectrochim. Acta, 1958, 13, 257.Google Scholar
  21. 21.
    Meyers, Lombardini and Bonoli, J. Amer. Chem. Soc., 1962, 84, 4603.Google Scholar
  22. 22.
    Leonard and Johnson. J. Amer. Chem. Soc., 1962, 84, 3701.Google Scholar
  23. 23.
    Cotton, Francis and Horrocks, J. Phys. Chem., 1960, 64, 1534.Google Scholar
  24. 24.
    Francis and Cotton, J. Chem. Soc., 1961, 2078.Google Scholar
  25. 25.
    Drago and Meek, J. Phys. Chem., 1961, 65, 1446.Google Scholar
  26. 26.
    Lappert and Smith, J. Chem. Soc., 1961, 3224.Google Scholar
  27. 27.
    Selbin, Bull and Holmes, J. Inorganic and Nuclear Chem., 1960, 16, 219.Google Scholar
  28. 28.
    Bellamy, Conduit, Pace and Williams, Trans. Faraday Soc., 1959, 35, 1677.Google Scholar
  29. 29.
    Biscarini and Ghersetti, Gazz. Chim. Ital., 1962, 92, 61.Google Scholar
  30. 30.
    Bellamy and Williams, J. Chem. Soc., 1957, 863.Google Scholar
  31. 31.
    Looney, Philips and Reilly, J. Amer. Chem. Soc., 1957, 79, 6136.Google Scholar
  32. 32.
    Williams, Pace and Jeacock, Spectrochim. Acta, 1964, 20, 225.Google Scholar
  33. 33.
    Owen and Sheppard, Proc Chem. Soc., 1963, 264.Google Scholar
  34. 34.
    Califano, Moccia, Scarpati and Speroni, J. Chem. Phys., 1957, 26, 1777.Google Scholar
  35. 35.
    Gowenlock, Spedding, Trotman and Whiffen, J. Chem. Soc., 1957, 3927.Google Scholar
  36. 36.
    Devlin and Hisatsune, Spectrochim. Acta, 1961, 17, 206.Google Scholar
  37. 37.
    Phillippe and Moore, Spectrochim. Acta, 1961, 17, 1004.Google Scholar
  38. 38.
    Shindo, Chem. and Pharm. Bull. Japan, 1958, 6, 117; 1959, 7, 791.Google Scholar
  39. 39.
    Katritzky, Beard and Coates, J. Chem. Soc., 1959, 3680.Google Scholar
  40. 40.
    Mirone, Atti. Accad. Naz. Lincei. Rend. Classe Sci. fis. mat. nat., 1963, 35, 530.Google Scholar
  41. 41.
    Tsoucaris, J. Chim. Phys., 1961, 58, 619.Google Scholar
  42. 42.
    Katritzky, Rec. Trav. Chim. Pays Bas., 1959, 78, 995.Google Scholar
  43. 43.
    Quagliano, Fujita, Franz, Phillips, Walmsley and Tyree, J. Amer. Chem. Soc., 1961, 83, 3770.Google Scholar
  44. 44.
    Shindo, Chem. and Pharm. Bull. Japan, 1960, 8, 33.Google Scholar
  45. 45.
    Klein and Berkowitz, J. Amer. Chem. Soc., 1959, 81, 5160.Google Scholar
  46. 46.
    Thomas and Chittenden, Chem. and Ind., 1961, 1913.Google Scholar
  47. 47.
    Thomas and Chittenden, Spectrochim. Acta, 1964, 20, 467.Google Scholar
  48. 48.
    Maiantz, Popov and Kabacnik, Optics and Spectroscopy, 1959, 7, 108.Google Scholar
  49. 49.
    Gersmann, Physich Chemische Metingen aan organische phosphor Verbindung, Thesis, Amsterdam 1956.Google Scholar
  50. 50.
    Dobbie and Straughan, Spectrochim. Acta, 1971, 27A, 255.Google Scholar
  51. 51.
    Ketelaar and Gersmann, Rec. Trav. Chim. Pays Bas., 1959, 78, 190.Google Scholar
  52. 52.
    Popov, Kabacnik and Majac, Adv. Chem. Moscow, 1961, 30, 846.Google Scholar
  53. 53.
    Mathis Noel, Boisdon, Vives and Mathis, Compt. Rendu. Acad. Sci. France, 1963, 257, 404.Google Scholar
  54. 54.
    Wolf, Mathis-Noel and Mathis, Bull. Soc. Chim. France, 1960, 124.Google Scholar
  55. 55.
    Wolf, Miquel and Mathis, Bull. Soc. Chim. France, 1963, 825.Google Scholar
  56. 56.
    Goncalves, Mathis and Wolf, Bull. Soc. Chim. France, 1961, 1595.Google Scholar
  57. 57.
    Jones and Katritzky, J. Chem. Soc., 1960, 4376.Google Scholar
  58. 58.
    Arnold and Bourseaux, Angew. Chem., 1958, 70, 539.Google Scholar
  59. 59.
    Haring, Helv. Chim. Acta, 1960, 43, 1826.Google Scholar
  60. 60.
    Miller, Miller and Rogers, J. Amer. Chem. Soc., 1958, 80, 1562.Google Scholar
  61. 61.
    Coe, Perry and Brown, J. Chem. Soc., 1957, 3604.Google Scholar
  62. 62.
    Lazarev and Akselrod, Optics and Spectroscopy, 1960, 9, 326.Google Scholar
  63. 63.
    Peppard, Ferraro and Mason, J. Inorganic and Nuclear Chem., 1958, 7, 231.Google Scholar
  64. 64.
    Peppard and Ferraro, J. Inorganic and Nuclear Chem., 1959, 10, 275.Google Scholar
  65. 65.
    Peppard, Feraro and Mason, J. Inorganic and Nuclear Chem., 1959, 12, 60.Google Scholar
  66. 66.
    Peppard, Ferraro and Mason, J. Inorganic and Nuclear Chem., 1961, 16, 246.Google Scholar
  67. 67.
    Ferraro and Andrejasich, J. Inorganic Nuclear Chem., 1964, 26, 377.Google Scholar
  68. 68.
    Thomas and Clark, Nature, 1963, 198, 855.Google Scholar
  69. 69.
    Smith, J. Inorganic and Nuclear Chem., 1960, 15, 95.Google Scholar
  70. 70.
    Braunholtz, Hall, Mann and Sheppard, J. Chem. Soc., 1959, 868.Google Scholar
  71. 71.
    Slovochotova, Anisimov, Kunickaja and Kolobova, Bull. Acad. Sci. U.R.S.S. Ser. Chim., 1961,71.Google Scholar
  72. 72.
    Gramstad, Acta Chem. Scand., 1961, 15, 1337.Google Scholar
  73. 73.
    Steger, Zeit. Electrochem., 1957, 61, 1004.Google Scholar
  74. 74.
    Mcivor and Hubley, Can. J. Chem., 1959, 37, 869.Google Scholar
  75. 75.
    Greckin and Sagidullin, Bull. Acad. Sci. U.R.S.S., 1960, 2135.Google Scholar
  76. 76.
    Sagidullin, Bull. Acad. Sci. U.R.S.S., phys. ser., 1958, 22, 1079.Google Scholar
  77. 77.
    Kabacnik, Giljarov and Cvetkov, Bull. Acad. Sci. U.R.S.S., 1959, 2135.Google Scholar
  78. 78.
    Griffen, Chem. and Ind., 1960, 1058.Google Scholar
  79. 79.
    Hanson and Bouck, J. Amer. Chem. Soc., 1957, 79, 5631.Google Scholar
  80. 80.
    Gramstad, Spectrochim. Acta, 1964, 20, 729.Google Scholar
  81. 81.
    Blindheim and Gramstad, Spectrochim. Acta, 1965, 21, 1073.Google Scholar
  82. 82.
    Cotton and Goodgame, J. Amer. Chem. Soc., 1960, 82, 5774.Google Scholar
  83. 83.
    Chittenden and Thomas, Spectrochim. Acta, 1964, 20, 1679.Google Scholar
  84. 84.
    Hoodge and Christen, Rec. Trav. Chim. Pays Bas, 1958, 77, 911.Google Scholar
  85. 85.
    Popov, Mastrjukova, Rodinova and Kabacnik, J. Gen. Chem. Moscow, 1959, 29(91), 1998.Google Scholar
  86. 86.
    Rockett, Applied Spectroscopy, 1962, 16, 39.Google Scholar
  87. 87.
    Vasil’Ev, Zhur. Obshchei Khim., 1963, 33, 874.Google Scholar
  88. 88.
    Tridot and Tudo, Bull. Soc. Chim. France, 1960, 1231.Google Scholar
  89. 89.
    Quinchon, Le Sech and Gryszkiewicz-Trochimowski, Bull. Soc. Chim. France, 1961, 735, 739; 1962, 169.Google Scholar
  90. 90.
    Zingaro and Hedges, J. Phys. Chem., 1961, 65, 1132.Google Scholar
  91. 91.
    Rao and Venkataraghavan, Spectrochim. Acta, 1962, 18, 541.Google Scholar
  92. 92.
    Lozach and Guillouzo, Bull. Soc. Chim. France, 1957, 1221.Google Scholar
  93. 93.
    Rao and Venkataraghavan, Can. J. Chem., 1961, 39, 1757.Google Scholar
  94. 94.
    Katritzky and Jones, Spectrochim. Acta, 1961, 17, 64.Google Scholar
  95. 95.
    Katritzky and Jones, J. Chem. Soc., 1960, 2947.Google Scholar
  96. 96.
    Bak, Hansen Nygaard and Pedersen, Acta Chem. Scand., 1958, 12, 1451.Google Scholar
  97. 97.
    Bellamy and Rogasch, J. Chem. Soc., 1960, 2218.Google Scholar
  98. 98.
    Pearson and Stasiak, Applied Spectroscopy, 1958, 12, 116.Google Scholar
  99. 99.
    Little, Poling and Leja, Can. J. Chem., 1961, 39, 745.Google Scholar
  100. 100.
    Shankarenaryana and Patel, Can. J. Chem., 1961, 39, 1633.Google Scholar
  101. 101.
    Spinner, J. Chem. Soc., 1960, 1237.Google Scholar
  102. 102.
    Susuki, Bull. Chem. Soc. Japan, 1962, 35, 1286; 1449, 1456.Google Scholar
  103. 103.
    Davies and Jones, J. Chem. Soc., 1958, 955.Google Scholar
  104. 104.
    Spinner, Spectrochim. Acta, 1959, 15, 95.Google Scholar
  105. 105.
    Kutzelnigg and Mecke, Spectrochim. Acta, 1961, 17, 530.Google Scholar
  106. 106.
    Scott and Wagner, J. Chem. Phys., 1959, 30, 465.Google Scholar
  107. 107.
    Milligan, Spinner and Swan, J. Chem. Soc., 1961, 1919.Google Scholar
  108. 108.
    Thorn, Can. J. Chem., 1960, 38, 1439, 2349.Google Scholar
  109. 109.
    Elmore, J. Chem. Soc., 1958, 3489.Google Scholar
  110. 110.
    Suresh, Ramachandran and Rao, J. Sci. Ind. Research (India), 1961, 20B, 203.Google Scholar
  111. 111.
    Sadler, J. Chem. Soc., 1961, 957.Google Scholar
  112. 112.
    Yamada, Omar and Hino, Chem. and Pharm. Bull. Japan, 1964, 12, 244.Google Scholar
  113. 113.
    Becher and Griffel, Chem. Ber., 1958, 91, 2025.Google Scholar
  114. 114.
    Collard-Charon and Renson, Bull. Soc. Chim. Beiges, 1963, 72, 149, 291, 304.Google Scholar
  115. 115.
    Spinner, J. Org. Chem., 1958, 23, 2037.Google Scholar
  116. 116.
    Jensen, Acta, Chem. Scand., 1963, 17, 551.Google Scholar
  117. 117.
    Cibisov and Pentin, J. Gen. Chem. Moscow, 1961, 31, 11.Google Scholar
  118. 118.
    Cotton, Barnes and Bannister, J. Chem. Soc., 1960, 2199.Google Scholar
  119. 119.
    Cotton and Goodgame, J. Chem. Soc., 1960, 5267; 1961, 2298, 3735.Google Scholar
  120. 120.
    Ghersetti and Pallotti, Gazz. Chim. Rome, 1963, 93, 1000.Google Scholar
  121. 121.
    Nyquist and Muelder, Spectrochim. Acta, 1966, 22, 1563.Google Scholar
  122. 122.
    Figueroa, Roig and Szmant, Spectrochim. Acta, 1966, 22, 1107.Google Scholar
  123. 123.
    Chen. Acta. Chim. Sin., 1965, 31, 29.Google Scholar
  124. 124.
    Husebye, Acta. Chem. Scand., 1965, 19, 774.Google Scholar
  125. 125.
    Korver, Veenland and De Boer, Rec Trav. Chim. Pays Bas, 1965, 84, 310.Google Scholar
  126. 126.
    Gingras, Supunchuk and Bayley, Can. J. Chem., 1965, 43, 1650.Google Scholar
  127. 127.
    Lumbroso and Montaudo, Bull. Chem. Soc. France, 1964, 2119.Google Scholar
  128. 128.
    Vazquez and Castrillon, Spectrochim. Acta, 1974, 30A, 2021.Google Scholar
  129. 129.
    Steudel Zeit. Naturforsch 1970, 25B, 156.Google Scholar
  130. 130.
    Dorris, Appl. Spectrosc, 1970, 24, 492.Google Scholar
  131. 131.
    Cazaux, Bastide, Chassaing and Maroni, Spectrochim. Acta, 1979, 35A, 15.Google Scholar
  132. 132.
    Green and Hellier, J. Chem. Soc. Perkin, 11, 1972, 458.Google Scholar
  133. 133.
    Cazaux and Maroni, Tetrahedron Letters, 1969, 3667.Google Scholar
  134. 134.
    Smith and Wu, Appl. Spectrosc, 1968, 22, 346.Google Scholar
  135. 135.
    Keat, Ross and Sharp, Spectrochim. Acta, 1971, 27A, 2219.Google Scholar
  136. 136.
    Raevsky, Verestichagin, Mumzhieva, Zyablikova, Alexandrova and Arbuzov. J. Mol. Structure, 1977, 36, 299.Google Scholar
  137. 137.
    Raevsky, J. Mol. Structure, 1973, 19, 275.Google Scholar
  138. 138.
    James and Morris, Spectrochim. Acta, 1978, 34A, 577.Google Scholar
  139. 139.
    Reynolds, in Progress in Inorganic Chemistry ed Lippard Wiley New York, 1970, Vol 12, p. 1.Google Scholar
  140. 140.
    Burgard and Leroy, J. Mol Structure, 1974, 20, 153.Google Scholar
  141. 141.
    Meunier and Forel, Spectrochim. Acta, 1973, 29A, 487.Google Scholar
  142. 142.
    Joly and Nicolau, Spectrochim. Acta, 1979, 35A, 281.Google Scholar
  143. 143.
    Goubeau and Lentz, Spectrochim. Acta, 1971, 27A, 1703.Google Scholar
  144. 144.
    Goldwhite and Previdi, Spectrochim. Acta, 1970, 26A, 1403.Google Scholar
  145. 145.
    Gramstad and Storesund, Spectrochim. Acta, 1970, 26A, 426.Google Scholar
  146. 146.
    Gramstad and Mundheim, Spectrochim. Acta, 1972, 28A, 1405.Google Scholar
  147. 147.
    Dahl, Klaboe and Gramstad, Spectrochim. Acta, 1969, 25A, 207.Google Scholar
  148. 148.
    Deacon and Green, Spectrochim. Acta, 1969, 25A, 355.Google Scholar
  149. 149.
    Muller, Koniger, Cyvin and Fadini, Spectrochim. Acta, 1973, 29A, 219.Google Scholar
  150. 150.
    Cyvin, Vizi, Muller and Krebs, J. Mol. Structure, 1969, 3, 173.Google Scholar
  151. 151.
    Olie and Stufkens, Spectrochim. Acta, 1976, 32A, 469.Google Scholar
  152. 152.
    Rojhantalab, Nibler and Wilkins, Spectrochim. Acta, 1976, 32A, 519.Google Scholar
  153. 153.
    Cormier, Nakamoto, Christophliemk and Muller, Spectrochim. Acta, 1974, 30A, 1059.Google Scholar
  154. 154.
    Burke and Fackler, Inorganic Chem., 1972, 11, 2744.Google Scholar
  155. 155.
    Garrigou-Lagrange, Andrieu and Mollier, Spectrochim. Acta, 1976, 32A, 477.Google Scholar
  156. 156.
    Andrieu and Mollier, Spectrochim. Acta, 1972, 28A, 785.Google Scholar
  157. 157.
    Andrieu and Mollier, Tetrahedron Letters, 1971, 1573.Google Scholar
  158. 158.
    Andrieu and Mollier, Bull. Soc. Chim. France, 1969, 831.Google Scholar
  159. 159.
    Ray, Sathyanarayana, Prasad and Patel, Spectrochim. Acta, 1973, 29A, 1578.Google Scholar
  160. 160.
    Coucouvanis, Progress in Inorganic Chem., 1970, 11, 233.Google Scholar
  161. 161.
    Geetharani and Sathyanarayana, Spectrochim. Acta, 1974, 30A, 2165.Google Scholar
  162. 162.
    Walter and Staglich, Spectrochim. Acta, 1974, 30A, 1739.Google Scholar
  163. 163.
    Desseyn, Jacob and Herman, Spectrochim. Acta, 1969, 25A, 1685.Google Scholar
  164. 164.
    Chaturverdi and Rao, Spectrochim. Acta, 1971, 27A, 65.Google Scholar
  165. 165.
    Anthoni, Neilsen, Borch and Klaboe, Spectrochim. Acta, 1978, 34A, 955.Google Scholar
  166. 166.
    Antoni, Heindriksen, Nielsen, Borch and Klaboe, Spectrochim. Acta, 1974, 30A, 1351.Google Scholar
  167. 167.
    Gayathri Devi, Sathyanarayana, and Volka, Spectrochim. Acta, 1978, 34A, 1137.Google Scholar
  168. 168.
    Gruger and Le Calve, Spectrochim. Acta, 1975, 31A, 581.Google Scholar
  169. 169.
    Gruger and Le Calve, Spectrochim. Acta, 1975, 31A, 595.Google Scholar

Copyright information

© L. J. Bellamy 1980

Authors and Affiliations

There are no affiliations available

Personalised recommendations