Skip to main content
SpringerLink
Log in

Effects of the Medium

  • Chapter
Quantum Chemistry of Organic Compounds

Abstract

Most organic reactions occur in solution and, naturally, any comprehensive analysis of the mechanism, kinetics, and thermodynamics of a given reaction must take account of effects of the medium, in other words, of the solvent effects. The number of publications is very great devoted to experimental research into the multifarious effects a solvent has on the rate and mechanism of organic reactions which were first detected about one hundred years ago by Menshutkin. How essential the effect of a solvent can be shows, for example, a comparison between the reaction of alkali hydrolysis of alkylhalogenides and esters in water and in the gas phase. The rate of the gas-phase reaction is by 20 orders of magnitude faster than in solution (see Sect. 5.1.1.4).

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Takashima K, Riveroc JM (1978) J ACS 100: 6128

    Article  CAS  Google Scholar 

  2. Menger FM (1983) Tetrahedron 39: 1013

    Article  CAS  Google Scholar 

  3. Kurtz AL (1964) Zh Vsesoyuzn Khim Obszh im DI Mendeleeva 29: 530

    Google Scholar 

  4. Thea S, Williams A (1985) Chem Soc Rev 15: 125

    Article  Google Scholar 

  5. Reichardt C (1979) Solvent effects in organic chemistry. VCH, New York

    Google Scholar 

  6. Entelis SG, Tiger RP (1973) The kinetic of reactions in liquid phase. Khimia, Moskow (in Russian)

    Google Scholar 

  7. Moelwyn-Hughes EA (1971) The chemical statics and kinetics of solutions. Academic Press, New York

    Google Scholar 

  8. Simkin BYa, Sheykhet II (1983) J Mol Liquids 27: 79

    Article  CAS  Google Scholar 

  9. Simkin BYa, Scheykhet II (1983) in: Kolotyrkin YaM (ed) Physical chemistry. Current problems. Khimia, Moskow (in Russian), p 148

    Google Scholar 

  10. Simkin BYa, Sheykhet II (1989) The quantum chemical and statistical theories of solutions. The calculational methods and their applications. Khimia, Moskow (in Russian)

    Google Scholar 

  11. Pierotti RA (1976) Chem Rev 76: 717

    Article  CAS  Google Scholar 

  12. Sinanoglu O (1974) Theor Chim Acta 33: 279

    Article  CAS  Google Scholar 

  13. Krebs C, Hoffman HJ, Weiss C (1981) Z Chem 227

    Google Scholar 

  14. Gesten JT, Spsae AM (1985) J ACS 107: 3786

    Article  Google Scholar 

  15. Tapia O (1982) in: Ratajczak H, Orville-Thomas WJ (eds) Molecular interactions. Wiley, New York, p 47

    Google Scholar 

  16. Under B (1967) Advan Chem Phys 12: 283

    Article  Google Scholar 

  17. McGreery JH, Chrystoffersen RE, Hall GG (1976) J ACS 98: 7191

    Article  Google Scholar 

  18. Rivail J-L, Rinaldi D (1976) Chem Phys 18: 233

    Article  CAS  Google Scholar 

  19. Klopman G (1967) Chem Phys Lett 1: 200

    Article  CAS  Google Scholar 

  20. Hoijtink GJ (1956) Ree Trav Chim Pays Bas 75: 487

    Article  CAS  Google Scholar 

  21. Tapia O, Goscinski O (1975) Mol Phys 29: 1653

    Article  CAS  Google Scholar 

  22. Constanciel R, Tapia O (1978) Theor Chim Acta 48: 75

    Article  CAS  Google Scholar 

  23. Simkin BYa (1978) Khim Geterocycl Soed N1 (without volume): 94

    Google Scholar 

  24. Simkin BYa, Minkin VI, Kosobutski VA, Zhdanov YuA J. Mol. structure (1975) 24: 237

    Article  Google Scholar 

  25. Gorb LG, Arbonin IA, Kharchevnikova NV (1984) Zh Phys Khim 58: 9

    CAS  Google Scholar 

  26. Pinsent BRW, Pearson L, Roughton FIW (1956) Trans Farad Soc 52: 1512

    Article  CAS  Google Scholar 

  27. Jonsson B, Karlstrom G. Wennerstrom H (1978) J ACS 100: 1658

    Article  CAS  Google Scholar 

  28. Miertus S, Kysel O, Krajcik K (1981) Chem Zvesti 35: 3

    CAS  Google Scholar 

  29. Miertus S, Bartos J (1980) Coll Czech Chem Comm 45: 2308

    CAS  Google Scholar 

  30. Constanciel R (1980) Theor Chim Acta 54: 123

    CAS  Google Scholar 

  31. Constanciel R (1986) Theor Chim Acta 69: 505

    Article  CAS  Google Scholar 

  32. Tapia O, Silvi B (1980) J Phys Chem 84: 2646

    Article  CAS  Google Scholar 

  33. Tapia O, Johannin G (1981) J Chem Phys 75: 3624

    Article  CAS  Google Scholar 

  34. Sanhueza JE, Tapia O (1982) THEOCHEM 89: 131

    Article  Google Scholar 

  35. Tapia O, Sussman F, Poulain E (1978) J Theor Biol 71: 49

    Article  CAS  Google Scholar 

  36. Karelson MM (1980) React Sposopbn Org Soed 17: 363

    Google Scholar 

  37. Miertus S, Scrocco E, Tomasi J (1981) Chem Phys 55: 177

    Article  Google Scholar 

  38. Bonaccorsi R, Cimiraglia R, Tomasi J (1983) J Comput Chem 4: 567

    Article  CAS  Google Scholar 

  39. Sheykhet II, Edelstein LL, Levchuk VN, Simkin BYa (1989) Khim Phys (in press)

    Google Scholar 

  40. Bonaccorsi R, Cimiraglia R, Miertus S, Tomasi J (1983) THEOCHEM 94: 11

    Article  Google Scholar 

  41. Abronin IA, Burstein KYa, Zhidomirov GM (1980) Zh Struct Khim 21: 145

    CAS  Google Scholar 

  42. Warshel A, Levitt M (1976) J Mol Biol 103: 227

    Article  CAS  Google Scholar 

  43. Noell JO, Morokuma K (1976) J Phys Chem 80: 2675

    Article  CAS  Google Scholar 

  44. Noell JO, Morokuma K (1977) J Phys Chem 81: 2295

    Article  CAS  Google Scholar 

  45. Simkin BYa, Sheykhet II, Levchuk VN (1984) Zh Struct Khim 25: 55

    CAS  Google Scholar 

  46. Warshel A (1979) J Phys Chem 83: 1640

    Article  CAS  Google Scholar 

  47. Levchuk VN, Sheykhet II, Simkin BYa (1988) J Mol Liquids 38: 35

    Article  CAS  Google Scholar 

  48. Burshtein KYa (1987) THEOCHEM 153: 195

    Article  Google Scholar 

  49. Warshel A (1981) Acc Chem Res 14: 284

    Article  CAS  Google Scholar 

  50. Warshel A, Russell ST (1984) Quart Rev Biophys 17: 283

    Article  CAS  Google Scholar 

  51. Burshtein KYa (1987) THEOCHEM 153: 203

    Article  Google Scholar 

  52. Burshtein KYa (1987) THEOCHEM 153: 209

    Article  Google Scholar 

  53. Politzer P, Truhlar DC (eds) (1981) Chemical applications of atomic and molecular electrostatic potentials, Plenum Press, New York

    Google Scholar 

  54. Tornasi J (1979) in: Daudel R (ed) Quantum theory of chemical reactions. Reidel, Amsterdam, p 191 (v 1)

    Google Scholar 

  55. Pullman A (1980) in: Daudel R (ed) Quantum theory of chemical reactions. Reidel, Amsterdam, p 1 (v 2)

    Google Scholar 

  56. Demontis P, Ercoli R, ES (1981) Thoer Chim Acta 58: 97

    Article  CAS  Google Scholar 

  57. Pullman A Perahia D (1978) Theor Chim Acta 48: 29

    Article  CAS  Google Scholar 

  58. Pullman A, Miertus S, Perahia D (1979) Theor Chim Acta 50: 317

    Article  CAS  Google Scholar 

  59. Williams IH (1987) J ACS 109: 6299

    Article  CAS  Google Scholar 

  60. Bertran J, Lledos A (1985) THEOCHEM 123: 211

    Article  Google Scholar 

  61. Zielinski ThJ, Poirier RA, Peterson MR, Csizmadia IG (1983) J Comput Chem 4: 419

    Article  CAS  Google Scholar 

  62. Ventura ON, Lledos A, Bonaccorsi R, Bertran J, Tomsai J (1987) Theor Chim Acta 72: 175

    Article  CAS  Google Scholar 

  63. Field MJ, Hiller IH (1987) J Chem Soc Perkin Trans 11: 617

    Google Scholar 

  64. Kochanski E (1981) in: Pullman B (ed) Intermolecular forces. The Jerusalem symposium on quantum chemistry and biochemistry. Reidel, Amsterdam, p 15 (v 14)

    Google Scholar 

  65. Pullman A (1976) in: Pullman B, Parr R (eds) The new world of quantum chemistry. Proceedings of the second international congress of quantum chemistry. Reidel, Amsterdam, p 149

    Google Scholar 

  66. Sheikhet II, Simkin BYa (1988) Zh Struct Khim 29: 84

    CAS  Google Scholar 

  67. Fresier BC, Jolly DL, Nordholm S (1983) Chem Phys 82: 369

    Article  Google Scholar 

  68. Chandrasekhar J, Smith SF, Jorgensen WL (1985) J ACS 107: 154

    Article  CAS  Google Scholar 

  69. Evanseck JD, Blake JF, Jorgensen WL (1987) J ACS 109: 2349

    Article  CAS  Google Scholar 

  70. Levchuk VN, Sheykhet II, Simkin BYa, Dorogan IV (1989) Zh Struct Khim (in press)

    Google Scholar 

  71. van der Zwan G, Hunes JT (1983) J Chem Phys 78: 4174

    Article  Google Scholar 

  72. van der Zwan G, Hynes JT (1984) Chem Phys 90: 21

    Article  Google Scholar 

  73. Bergsma JP, Gertner BJ, Wilson KR, Hynes JT (1987) J Chem Phys 86: 1356

    Article  CAS  Google Scholar 

  74. Gertner BJ, Bergsma JP, Wilson KR, Lee S, Hynes JT (1987) J Chem Phys 86: 1377

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Physical and Organic Chemistry, Rostov University, 344711, Rostov on Don, USSR

    Professor Vladimir I. Minkin, Professor Boris Ya. Simkin & Dr. Ruslan M. Minyaev

Authors
  1. Professor Vladimir I. Minkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Professor Boris Ya. Simkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Dr. Ruslan M. Minyaev
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

Copyright information

© 1990 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Minkin, V.I., Simkin, B.Y., Minyaev, R.M. (1990). Effects of the Medium. In: Quantum Chemistry of Organic Compounds. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-75679-5_3

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-75679-5_3

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-75681-8

  • Online ISBN: 978-3-642-75679-5

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation