Advertisement

Journal of Structural Chemistry

, Volume 7, Issue 2, pp 283–320 | Cite as

Steric hindrance and conformation in aromatic molecules

  • R. L. Avoyan
  • Yu. T. Struchkov
  • V. G. Dashevskii
Reviews

Keywords

Physical Chemistry Inorganic Chemistry Steric Hindrance Aromatic Molecule 
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.

Literature cited

  1. 1.
    M. Born and J. R. Oppenheimer, Ann. Phys. (Lpz.),84, 457 (1927).Google Scholar
  2. 2.
    A. I. Kitaigorodskii, Organic Crystal Chemistry [in Russian], Izd. AN SSSR, Moscow (1955).Google Scholar
  3. 3.
    A. I. Kitaigorodskii, Dokl. AN SSSR,137, 116 (1961); Tetrahedron,9, 183 (1960).Google Scholar
  4. 4.
    F. Bell and D. H. Waring, J. Chem. Soc., 2689 (1949).Google Scholar
  5. 5.
    L. Pauling, Nature of the Chemical Bond, Cornell University Press, 3rd Edition (1960).Google Scholar
  6. 6.
    A. I. Kitaigorodskii,X-ray Structure Analysis [in Russian], Gostekhizdat, Moscow (1950).Google Scholar
  7. 7.
    G. Briegleb, Fortschr. Chem. Forsch.,1, 642 (1950).Google Scholar
  8. 8.
    Tables of Interatomic Distances and Configuration in Molecules and Ions, Edited by L. E. Sutton, London (1958).Google Scholar
  9. 9.
    I. Dostrovsky, E. D. Hughes, and C. K. Ingold, J. Chem. Soc., 173 (1946).Google Scholar
  10. 10.
    T. L. Khotsyanova, A. I. Kitaigorodskii, and Yu. T. Struchkov,Zh. Fiz. Khimii,27, 781, 1341 (1953).Google Scholar
  11. 11.
    I. N. Strel'tsova and Yu. T. Struchkov, Zh. Strukt. Khim.,2, 312 (1961).Google Scholar
  12. 12.
    I. N. Strel'tsova and Yu. T. Struchkov, Izv. AN SSSR, OKhN,2, 250 (1961).Google Scholar
  13. 13.
    G. Gafner and F. H. Herbstein, Acta Crystallogr.,13, 702 (1960).Google Scholar
  14. 14.
    A. Tulinsky and J. G. White, Acta Crystallogr.,11, 7 (1958).Google Scholar
  15. 15.
    W. Bolton, Nature,201, 987 (1964).Google Scholar
  16. 16.
    J. Hirschfelder, C. Curtiss, and R. Bird, Molecular Theory of Gases and Liquids [Russian translation], IL, Moscow (1961).Google Scholar
  17. 17.
    T. L. Hill, J. Chem. Phys.,16, 399 (1948).Google Scholar
  18. 18.
    L. S. Bartell, J. Chem. Phys.,32, 827 (1960).Google Scholar
  19. 19.
    Ph. Coppens, J. Chem. Phys.,36, 2523 (1962).Google Scholar
  20. 20.
    S. Weisbaum, I. Beers, and G. Herrman, J. Chem. Phys.,23, 1601 (1955).Google Scholar
  21. 21.
    K. Lonsdale, H. J. Milledge, and K. V. K. Rao, Proc. Roy. Soc.,A255, 82 (1960).Google Scholar
  22. 22.
    C. L. Coulter and K. N. Trueblood, Acta Crystallogr.,16, 667 (1963).Google Scholar
  23. 23.
    A. O. McIntosh, J. M. Robertson, and V. Vand, J. Chem. Soc., 1661 (1954).Google Scholar
  24. 24.
    G. Gafner and F. H. Herbstein, Nature,200, 130 (1963).Google Scholar
  25. 25.
    E. Harnik and G. M. J. Schmidt, J. Chem. Soc., 3295 (1954).Google Scholar
  26. 26.
    P. J. Wheatley, J. Chem. Soc., 4936 (1961).Google Scholar
  27. 27.
    K. S. Pitzer and W. E. Donath, J. Amer. Chem. Soc.,81, 3212 (1959).Google Scholar
  28. 28.
    Steric Effect in Organic Chemistry, Edited by M. S. Newman [Russian translation], IL, Moscow (1960).Google Scholar
  29. 29.
    E. B. Wilson, Jr., Adv. Chem. Phys.,2, 367 (1959).Google Scholar
  30. 30.
    J. B. Hendrickson, J. Amer. Chem. Soc.,83, 4537 (1961).Google Scholar
  31. 31.
    S. Mizyshima, Structure of Molecules and Internal Rotation [Russian translation], IL, Moscow (1957).Google Scholar
  32. 32.
    J. D. Dunitz and V. Prelog, Ang. Chem.,72, 896 (1960).Google Scholar
  33. 33.
    O. Bastiansen and O. Hassel, Acta Chem. Scand.,1, 489 (1947).Google Scholar
  34. 34.
    H. de Laszlo, J. Chem. Phys.,2, 892 (1934).Google Scholar
  35. 35.
    T. Sakurai, M. Sundaralingam, and G. A. Jeffrey, Acta Crystallogr.,16, 354 (1963).Google Scholar
  36. 36.
    G. Gafner and F. H. Herbstein, Acta Crystallogr.,13, 706 (1960).Google Scholar
  37. 37.
    C. Dean, M. Pollak, B. M. Graven, and G. A. Jeffrey, Acta Crystallogr.,11, 710 (1958).Google Scholar
  38. 38.
    J. M. Robertson, Pro. Roy. Soc.,A142, 659 (1941).Google Scholar
  39. 39.
    A. Kossiakoff and H. D. Springall, J. Amer. Chem. Soc.,63, 2223 (1941).Google Scholar
  40. 40.
    A. K. Pant, Acta Crystallogr.,19, 440 (1965).Google Scholar
  41. 41.
    G. Charbonneau, et al., Bull. Soc. Franc. Minéral et Crystallogr.,88, 147 (1965).Google Scholar
  42. 42.
    G. Gafner and F. H. Herbstein, J. Chem. Soc., 5290 (1964).Google Scholar
  43. 43.
    T. A. Babushkina, T. L. Khotsyanova, and G. K. Semin, Zh. Strukt. Khim.,6, 307 (1965).Google Scholar
  44. 44.
    A. Almenningen, O. Bastiansen,et al., Acta Chem. Scand.,18, 2115 (1964).Google Scholar
  45. 45.
    E. E. Ferguson, R. L. Hudson, J. R. Nielsen, and D. C. Smith, J. Chem. Phys.,21, 1464 (1954).Google Scholar
  46. 46.
    L. Delbouille, J. Chem. Phys.,25, 182 (1956).Google Scholar
  47. 47.
    K. Lonsdale, Proc. Roy. Soc.,A133, 536 (1931).Google Scholar
  48. 48.
    T. Sakurai, Acta Crystallogr.,15, 1164 (1962).Google Scholar
  49. 49.
    S. C. Chu, G. A. Jeffrey, and T. Sakurai, Acta Crystallogr.,15, 661 (1962).Google Scholar
  50. 50.
    L. L. Barricelli and O. Bastiansen, Tidsskr. Kjemi Bergv.,9, 3 (1949).Google Scholar
  51. 51.
    T. Sakurai, Acta Crystallogr.,15, 445 (1962).Google Scholar
  52. 52.
    D. Rabinovich and G. M. J. Schmidt, J. Chem. Soc., 2030 (1964); Acta Crystallogr.,16, 13, A57 (1963).Google Scholar
  53. 53.
    G. Ferguson and G. A. Sim, Acta Crystallogr.,14, 1262 (1961).Google Scholar
  54. 54.
    G. Ferguson and G. A. Sim, Acta Crystallogr.,15, 346 (1962); Proc. Chem. Soc., 162 (1961).Google Scholar
  55. 55.
    W. M. Macintyre and M. Zirakzadeh, Acta Crystallogr.,17, 1305 (1964).Google Scholar
  56. 56.
    I. Okaya and R. Pepinsky, Acta Crystallogr.,10, 324 (1957).Google Scholar
  57. 57.
    S. F. Darlow, Acta Crystallogr.,14, 159 (1961).Google Scholar
  58. 58.
    W. Cochran, Acta Crystallogr.,6, 260 (1953); M. Sundaralingam and L. H. Jensen, Acta Crystallogr.,18, 1053 (1965).Google Scholar
  59. 59.
    J. M. Brown and R. E. March, Acta Crystallogr.,16, 191 (1963).Google Scholar
  60. 60.
    P. J. Wheatley, J. Chem. Soc., Suppl.,2, 6036 (1964).Google Scholar
  61. 61.
    M. Sax, P. Beurskens, and S. Chu, Acta Crystallogr.,18, 252 (1965).Google Scholar
  62. 62.
    Ph. Coppens and G. M. J. Schmidt, Acta Crystallogr.,17, 222 (1964).Google Scholar
  63. 63.
    Ph. Coppens, Acta Crystallogr.,15, 573 (1964).Google Scholar
  64. 64.
    Yu. T. Struchkov and T. L. Khotsyanova, Izv. AN SSSR, OKhN,8, 1369 (1960).Google Scholar
  65. 65.
    J. Donohue and K. N. Trueblood, Acta Crystallogr.,9, 960 (1956).Google Scholar
  66. 66.
    G. S. Zhdanov and G. A. Gol'der, Zh. Fiz. Khimii,29, 1248 (1955).Google Scholar
  67. 67.
    J. Trotter, Acta Crystallogr.,12, 605 (1959).Google Scholar
  68. 68.
    G. A. Gol'der, G. S. Zhdanov, and M. M. Umanskii, DAN SSSR,92, 311 (1953).Google Scholar
  69. 69.
    G. Huse and H. M. Powell, J. Chem. Soc., 1398 (1941).Google Scholar
  70. 70.
    E. Grison, Acta Crystallogr.,2, 410 (1949).Google Scholar
  71. 71.
    G. B. Jensen, Acta Crystallogr.,17, 243 (1964).Google Scholar
  72. 72.
    H. H. Cody and A. C. Larson, Acta Crystallogr.,18, 485 (1965).Google Scholar
  73. 73.
    W. C. Hamilton and C. J. La Placa, J. Amer. Chem. Soc.,86, 2289 (1964).Google Scholar
  74. 74.
    A. T. McPhail and G. A. Sim, J. Chem. Soc., 227 (1965).Google Scholar
  75. 75.
    G. Ferguson and G. A. Sim, J. Chem. Soc., 1767 (1962).Google Scholar
  76. 76.
    J. Trotter, Acta Crystallogr.,14, 244 (1961).Google Scholar
  77. 77.
    K. J. Watson, Nature,188, 1102 (1960).Google Scholar
  78. 78.
    M. P. Marson, Acta Crystallogr.,18, 851 (1965).Google Scholar
  79. 79.
    M. A. Viswamitra and S. N. Vaidga, Z. Kristallogr.,121, 472 (1965).Google Scholar
  80. 80.
    A. Almenningen and O. Bastiansen, Kgl. Norske Vid.Selsk. Skr., 4 (1958).Google Scholar
  81. 81.
    M. J. Dewar and H. N. Schmeising, Tetrahedron,5, 166 (1959).Google Scholar
  82. 82.
    J. Trotter, Acta Crystallogr.,14, 1135 (1961).Google Scholar
  83. 83.
    E. G. Boonstra, Acta Crystallogr.,16, 816, (1963).Google Scholar
  84. 84.
    O. Bastiansen and L. Smedvik, Acta Chem. Scand.,8, 1593 (1954).Google Scholar
  85. 85.
    O. Bastiansen, Acta Chem. Scand.,4, 926 (1950).Google Scholar
  86. 86.
    O. Bastiansen, Acta Chem. Scand.,3, 408 (1949).Google Scholar
  87. 87.
    D. L. Smare, Acta Crystallogr.,1, 150 (1948).Google Scholar
  88. 88.
    F. Fowweather and A. Hargreaves, Acta Crystallogr.,3, 81 (1950).Google Scholar
  89. 89.
    F. Fowweather, Acta Crystallogr.,5, 820 (1952).Google Scholar
  90. 90.
    F. H. Westheimer and J. E. Mayer, J. Chem. Phys.,14, 733 (1946).Google Scholar
  91. 91.
    F. H. Westheimer, J. Chem. Phys.,15, 252 (1947).Google Scholar
  92. 92.
    M. Rieger and F. H. Westheimer, J. Amer. Chem. Soc.,72, 19 (1950).Google Scholar
  93. 93.
    L. W. Pickett, Proc. Roy. Soc.,142A, 333 (1933).Google Scholar
  94. 94.
    L. W. Pickett, J. Amer. Chem. Soc.,58, 2299 (1936).Google Scholar
  95. 95.
    O. Bastiansen, Acta Chem. Scand.,6, 205 (1952).Google Scholar
  96. 96.
    M. S. Farag, Acta Crystallogr.,7, 117 (1954).Google Scholar
  97. 97.
    A. Damiani, E. Giglio, and A. Ripamonti, Acta Crystallogr.,19, 161 (1965).Google Scholar
  98. 98.
    D. Belitskus and G. A. Jeffrey, Spectrochim. Acta,21, 1563 (1965).Google Scholar
  99. 99.
    K. Lonsdale, Z. Krist.,97, 91 (1937).Google Scholar
  100. 100.
    A. A. Almenningen, O. Bastiansen, and P. N. Skacke, Acta Chem. Scand.,12, 1215 (1958).Google Scholar
  101. 101.
    A. H. Gomes de Mesquita, C. H. Mac Gillavry, and K. Eriks, Acta Crystallogr.,18, 437 (1965).Google Scholar
  102. 102.
    P. Andersen and B. Klewe, Acta Chem. Scand.,19, 791 (1965).Google Scholar
  103. 103.
    P. Andersen and B. Klewe, Acta Chem. Scand.,16, 1817 (1962).Google Scholar
  104. 104.
    P. Andersen, Acta Chem. Scand.,19, 629 (1965).Google Scholar
  105. 105.
    M. Sundaralingram and L. H. Jensen, J. Amer. Chem. Soc.85, 3302 (1963).Google Scholar
  106. 106.
    G. C. Hampson and J. M. Robertson, J. Chem. Soc., 409 (1941).Google Scholar
  107. 107.
    C. P. Fenimore, J. Amer. Chem. Soc.,72, 3226 (1957).Google Scholar
  108. 108.
    S. C. Wallwork, Acta Crystallogr.,14, 375 (1961).Google Scholar
  109. 109.
    I. L. Karle and K. S. Dragonette, Acta Crystallogr.,19, 500 (1965).Google Scholar
  110. 110.
    T. L. Khotsyanova and Yu. T. Struchkov, Kristallografiya,1, 669 (1956).Google Scholar
  111. 111.
    T. L. Khotsyanova, Kristallografiya,1, 524 (1956);2, 51 (1957).Google Scholar
  112. 112.
    D. W. J. Cruickshank, Acta Crystallogr.,10, 504 (1957).Google Scholar
  113. 113.
    D. W. J. Cruickshank, Acta Crystallogr.,9, 915 (1956).Google Scholar
  114. 114.
    M. A. Davydova and Yu. T. Struchkov, Zh. Strukt. Khimii,2, 69 (1961);3, 184 (1962).Google Scholar
  115. 115.
    G. Gafner and F. H. Herbstein, Acta Crystallogr.,15, 1081 (1962).Google Scholar
  116. 116.
    M. A. Davydova and Yu. T. Struchkov, Zh. Strukt. Khimii,6, 113 (1965).Google Scholar
  117. 117.
    M. B. Jameson and B. R. Penfold, J. Chem. Soc., 528 (1965).Google Scholar
  118. 118.
    H. W. W. Whrlich, Acta Crystallogr.,10, 699 (1957).Google Scholar
  119. 119.
    R. L. Avoyan and Yu. T. Struchkov, Zh. Strukt. Khimii,2, 119 (1961).Google Scholar
  120. 120.
    R. L. Avoyan and Yu. T. Struchkov, Zh. Strukt. Khimii,5, 424 (1964).Google Scholar
  121. 121.
    D. M. Donaldson and J. M. Robertson, J. Chem. Soc., 17 (1953).Google Scholar
  122. 122.
    J. Beintema, Acta Crystallogr.,18, 647 (1965).Google Scholar
  123. 123.
    J. Gaultier and Chr. Hauw, Acta Crystallogr.,18, 179 (1965).Google Scholar
  124. 124.
    J. Gaultier and Chr. Hauw, Acta Crystallogr.,19, 585 (1965).Google Scholar
  125. 125.
    J. Gaultier and Chr. Hauw,C. r. Acad. Sci.,260, 2831 (1965).Google Scholar
  126. 126.
    M. Breton, C. r. Acad. Sci.,260, 5275 (1965).Google Scholar
  127. 127.
    J. Gaultier and Chr. Hauw, Acta Crystallogr.,19, 580 (1965).Google Scholar
  128. 128.
    J. Gaultier and Chr. Hauw, Acta Crystallogr.,18, 604 (1965).Google Scholar
  129. 129.
    J. C. Metras, Acta Crystallogr.,14, 153 (1961).Google Scholar
  130. 130.
    M. Breton, C. r. Acad. Sci.,258, 3489 (1964).Google Scholar
  131. 131.
    M. Bailey, Acta Crystallogr.,11, 103 (1958).Google Scholar
  132. 132.
    L. A. Chetkina and G. A. Gol'der, Kristallografiya,8, 582 (1963); L. A. Chetkina, Candidate Thesis, IK AN SSSR (1966).Google Scholar
  133. 133.
    Z. A. Akopyan and Yu. T. Struchkov, Zh. Strukt. Khimii,5, 511 (1964);6, 729 (1965).Google Scholar
  134. 134.
    J. Trotter, Acta Crystallogr.,13, 95 (1960).Google Scholar
  135. 135.
    J. Trotter, Acta Crystallogr.,13, 732 (1960).Google Scholar
  136. 136.
    J. Trotter, Acta Crystallogr.,12, 237 (1959).Google Scholar
  137. 137.
    J. Trotter, Acta Crystallogr.,12, 232 (1959).Google Scholar
  138. 138.
    J. Trotter, Acta Crystallogr.,12, 922 (1959).Google Scholar
  139. 139.
    W. A. C. Brown, J. Trotter, and J. M. Robertson, Proc. Chem. Soc., 115 (1961).Google Scholar
  140. 140.
    R. L. Avoyan, A. I. Kitaigorodskii, and Yu. T. Struchkov, Zh. Strukt. Khimii,5, 420 (1964).Google Scholar
  141. 141.
    D. A. Norton and J. M. Ohrt, Nature,197, 450 (1963).Google Scholar
  142. 142.
    F. L. Hirshfeld, J. Chem. Soc., 2126 (1963).Google Scholar
  143. 143.
    J. M. Robertson, V. C. Sinclair, and J. Trotter, Acta Crystallogr.,14, 705 (1961).Google Scholar
  144. 144.
    C. A. Coulson, Industrie Chimique Belge,2, 149 (1963).Google Scholar
  145. 145.
    J. F. D. Mills and S. C. Nyburg, J. Chem. Soc., 308 (1963).Google Scholar
  146. 146.
    S. C. Nyburg, Acta Crystallogr.,7, 779 (1954).Google Scholar
  147. 147.
    F. Bell, J. Chem. Soc., 5047 (1952).Google Scholar
  148. 148.
    H. Pandraud, Acta Crystallogr.,14, 901 (1961).Google Scholar
  149. 149.
    H. T. Hall and R. B. Turner, Chem. and Ind., 1177 (1953).Google Scholar
  150. 150.
    M. S. Newman, W. B. Lutz, and D. Lednicer, J. Amer. Chem. Soc.,77, 3420 (1955).Google Scholar
  151. 151.
    F. H. Herbstein and G. M. J. Schmidt, J. Chem. Soc., 3314 (1954).Google Scholar
  152. 152.
    F. H. Herbstein and G. M. J. Schmidt, J. Chem. Soc., 3302 (1954).Google Scholar
  153. 153.
    F. L. Hirshfeld, S. Sandler, and G. M. J. Schmidt, J. Chem. Soc., 2108 (1963).Google Scholar
  154. 154.
    E. D. Bergmann, E. H. Fischer, and B. Pullman, J. Chem. Phys.48, 356 (1951).Google Scholar
  155. 155.
    M. S. Newman and W. B. Wheatly, J. Amer. Chem. Soc.,70, 1913 (1948).Google Scholar
  156. 156.
    T. N. Margulis, Acta Crystallogr.,19, 857 (1965).Google Scholar
  157. 157.
    F. R. Ahmed and J. Trotter, Acta Crystallogr.,16, 503 (1963).Google Scholar
  158. 158.
    J. M. Robertson and J. Trotter, J. Chem. Soc., 2614 (1959).Google Scholar
  159. 159.
    M. G. Rossman, J. Chem. Soc., 2607 (1959).Google Scholar
  160. 160.
    R. P. Ferrier and I. Iball, Acta Crystallogr., 16, 269 (1963).Google Scholar
  161. 161.
    Progress in Stereochemistry, Edited by W. Klyne and P. de La Mare [Russian translation], Goskhimizdat, Moscow (1961), p. 81.Google Scholar
  162. 162.
    C. J. Brown, J. Chem. Soc., 3265 (1953).Google Scholar
  163. 163.
    B. Kamenar and C. K. Prout, J. Chem. Soc., 4838 (1965).Google Scholar
  164. 164.
    M. Liang, Proc. Chem. Soc., 343 (1964).Google Scholar
  165. 165.
    P. K. Gantzel and K. N. Trueblood, Acta Crystallogr.,18, 958 (1965).Google Scholar
  166. 166.
    D. H. Whiffen, Phil. Trans.,A248, 131 (1955).Google Scholar
  167. 167.
    R. H. Boyd, Abstr. 19th Annual Calorimetry Conf., Washington (1964).Google Scholar
  168. 168.
    C. J. Brown, J. Chem. Soc., 3278 (1953).Google Scholar
  169. 169.
    A. W. Hauson, Acta Crystallogr.,15, 956 (1962).Google Scholar
  170. 170.
    M. D. Laing and K. N. Trueblood, Acta Crystallogr.,19, 373 (1965).Google Scholar
  171. 171.
    N. D. Jones, R. E. Marsh, and J. H. Hichards, Acta Crystallogr.,19, 330 (1965).Google Scholar

Copyright information

© Consultants Bureau 1967

Authors and Affiliations

  • R. L. Avoyan
    • 1
  • Yu. T. Struchkov
    • 1
  • V. G. Dashevskii
    • 1
  1. 1.Institute of Heteroorganic CompoundsAcademy of SciencesUSSR

Personalised recommendations