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Volumn 5, Issue 6, 1999, Pages 1917-1930

Theoretical models and experimental data for reactions between water and protonated alcohols: Substitution and elimination mechanisms

(2) Uggerud, Einar a Bache Andreassen, Lihn a

a UNIVERSITY OF OSLO (Norway)

Author keywords

Ab initio calculations; Cluster compounds; Eliminations; Mass spectrometry; Nucleophilic substitutions

Indexed keywords

ALCOHOL; METHYL GROUP; WATER;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; FOURIER ANALYSIS; HYDROGEN BOND; MODEL; PROTON TRANSPORT; QUANTUM CHEMISTRY; STRUCTURE ANALYSIS;

EID: 0032977078 PISSN: 09476539 EISSN: None Source Type: Journal
DOI: 10.1002/(SICI)1521-3765(19990604)5:6<1917::AID-CHEM1917>3.0.CO;2-R Document Type: Article

Times cited : (45)

References (70)

1
- 0004181494
- Wiley, New York
- W. H. Saunders, Jr., A. F. Cockerill, Mechanisms of Elimination Reactions, Wiley, New York, 1973.
- (1973) Mechanisms of Elimination Reactions
- Saunders W.H., Jr.¹ Cockerill, A.F.²

2
- 0003887404
- Harper and Row, New York
- T. H. Lowry, K. S. Richardson, Mechanism and Theory in Organic Chemistry, Harper and Row, New York, 1981.
- (1981) Mechanism and Theory in Organic Chemistry
- Lowry, T.H.¹ Richardson, K.S.²

3
- 0003992011
- Elsevier, Amsterdam
- F. Ruff, I. G. Csizmadia, Organic Reactions. Equilibria, Kinetics and Mechanism, Elsevier, Amsterdam, 1994.
- (1994) Organic Reactions. Equilibria, Kinetics and Mechanism
- Ruff, F.¹ Csizmadia, I.G.²

4
- 0004105856
- Longman Scientific and Technical, Burnt Mill, Harlow, Essex
- N. Isaacs, Physical Organic Chemistry, Longman Scientific and Technical, Burnt Mill, Harlow, Essex, 1995.
- (1995) Physical Organic Chemistry
- Isaacs, N.¹

5
- 37049151007
- W. A. Cowdrey, E. D. Hughes, C. K. Ingold, S. Masterman, A. D. Scott, J. Chem. Soc. 1937, 1252.
- (1937) J. Chem. Soc. , pp. 1252
- Cowdrey, W.A.¹ Hughes, E.D.² Ingold, C.K.³ Masterman, S.⁴ Scott, A.D.⁵

6
- 0000088379
- J. Dale, J. Chem. Educ. 1998, 75, 1482.
- (1998) J. Chem. Educ. , vol.75 , pp. 1482
- Dale, J.¹

7
- 33947468159
- S. Winstein, E. Clippinger, A. H. Fainberg, R. Heck, G. C. Robinson, J. Am. Chem. Soc. 1956, 78, 328.
- (1956) J. Am. Chem. Soc. , vol.78 , pp. 328
- Winstein, S.¹ Clippinger, E.² Fainberg, A.H.³ Heck, R.⁴ Robinson, G.C.⁵

8
- 0003467672
- Wiley, New York
- J. March, Advanced Organic Chemistry, Wiley, New York, 1985.
- (1985) Advanced Organic Chemistry
- March, J.¹

9
- 33845557174
- T. W. Bentley, C. T. Bowen, D. H. Morten, P. von R. Schleyer, J. Am. Chem. Soc. 1981, 103, 5466.
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 5466
- Bentley, T.W.¹ Bowen, C.T.² Morten, D.H.³ Schleyer, P.V.R.⁴

10
- 33646098132
- T. W. Bentley, C. T. Bowen, J. Chem. Soc. Perkin Trans. II 1978, 557.
- (1978) J. Chem. Soc. Perkin Trans. II , pp. 557
- Bentley, T.W.¹ Bowen, C.T.²

11
- 37049099359
- W. P. Jencks, Chem. Soc. Rev. 1982, 10, 345.
- (1982) Chem. Soc. Rev. , vol.10 , pp. 345
- Jencks, W.P.¹

12
- 37049171389
- I. Dostrovsky, E. D. Hughes, C. K. Ingold, J. Chem. Soc. 1946, 173.
- (1946) J. Chem. Soc. , pp. 173
- Dostrovsky, I.¹ Hughes, E.D.² Ingold, C.K.³

13
- 0001563975
- T. W. Bentley, C. T. Bowen, W. Parker, C. I. F. Watt, J. Am. Chem. Soc. 1979, 101, 2486.
- (1979) J. Am. Chem. Soc. , vol.101 , pp. 2486
- Bentley, T.W.¹ Bowen, C.T.² Parker, W.³ Watt, C.I.F.⁴

14
- 0003792563
- Elsevier, Amsterdam
- P. Vogel, Carbocation Chemistry, Elsevier, Amsterdam, 1985.
- (1985) Carbocation Chemistry
- Vogel, P.¹

15
- 0346287682
- W. Klopper, W. Kutzelnigg, J. Phys. Chem. 1990, 94, 5652-5630.
- (1990) J. Phys. Chem. , vol.94 , pp. 5652-15630
- Klopper, W.¹ Kutzelnigg, W.²

16
- 0348178425
- J. E. Del-Bene, D. H. Aue, I. Shavitt, J. Am. Chem. Soc. 1992, 114, 1631.
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 1631
- Del-Bene, J.E.¹ Aue, D.H.² Shavitt, I.³

17
- 0000497409
- G. Olah, Angew. Chem. 1995, 107, 1519; Angew. Chem. Int. Ed. Engl. 1995, 34, 1393.
- (1995) Angew. Chem. , vol.107 , pp. 1519
- Olah, G.¹

18
- 33748220638
- G. Olah, Angew. Chem. 1995, 107, 1519; Angew. Chem. Int. Ed. Engl. 1995, 34, 1393.
- (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 1393

19
- 0004105855
- Wiley New York
- N2 Reaction, Wiley New York, 1992.
- (1992) N2 Reaction
- Shaik, S.S.¹ Schlegel, H.B.² Wolfe, S.³

20
- 0004143523
- Springer, Berlin
- V. I. Minkin, B. Y. Simkin, R. M. Minyaev, Quantum Chemistry of Organic Compounds, Springer, Berlin, 1990.
- (1990) Quantum Chemistry of Organic Compounds
- Minkin, V.I.¹ Simkin, B.Y.² Minyaev, R.M.³

21
- 0001004129
- L. J. de Koning, N. M. M. Nibbering, S. L. van Orden, F. H. Laukien, Int. J. Mass Spectrom. Ion Proc. 1997, 165/166, 209.
- (1997) Int. J. Mass Spectrom. Ion Proc. , vol.165-166 , pp. 209
- De Koning, L.J.¹ Nibbering, N.M.M.² Van Orden, S.L.³ Laukien, F.H.⁴

22
- 0003592354
- Maruzen, Tokyo
- Y. Ikezoe, S. Matsuoka, M. Takebe, A. Viggiano, Gas Phase Ion-Molecule Reaction Rate Constants Through 1986, Maruzen, Tokyo, 1987.
- (1987) Gas Phase Ion-Molecule Reaction Rate Constants Through 1986
- Ikezoe, Y.¹ Matsuoka, S.² Takebe, M.³ Viggiano, A.⁴

23
- 84871008794
- Gaussian, Pittsburgh, PA
- M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. A. Keith, G. A. Peterson, J. A. Mongomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Reploge, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. J. P. Stewart, M. Head-Gordon, C. Gonzalez, J. A. Pople, GAUSSIAN 94, Gaussian, Pittsburgh, PA, 1994.
- (1994) GAUSSIAN 94
- Frisch, M.J.¹ Trucks, G.W.² Schlegel, H.B.³ Gill, P.M.W.⁴ Johnson, B.G.⁵ Robb, M.A.⁶ Cheeseman, J.R.⁷ Keith, T.A.⁸ Peterson, G.A.⁹ Mongomery, J.A.¹⁰ Raghavachari, K.¹¹ Al-Laham, M.A.¹² Zakrzewski, V.G.¹³ Ortiz, J.V.¹⁴ Foresman, J.B.¹⁵ Cioslowski, J.¹⁶ Stefanov, B.B.¹⁷ Nanayakkara, A.¹⁸ Challacombe, M.¹⁹ Peng, C.Y.²⁰ more..

24
- 33748545144
- P. C. Hariharan, J. A. Pople, Theoret. Chim. Acta 1973, 28, 213.
- (1973) Theoret. Chim. Acta , vol.28 , pp. 213
- Hariharan, P.C.¹ Pople, J.A.²

25
- 36549091139
- M. J. Frisch, J. A. Pople, J. S. Binkley, J. Chem. Phys. 1984, 80, 3265.
- (1984) J. Chem. Phys. , vol.80 , pp. 3265
- Frisch, M.J.¹ Pople, J.A.² Binkley, J.S.³

26
- 2342430094
- C. C. J. Roothan, Rev. Mod. Phys. 1951, 23, 69.
- (1951) Rev. Mod. Phys. , vol.23 , pp. 69
- Roothan, C.C.J.¹

27
- 6944251055
- C. Møller, M. S. Plesset, Phys. Rev. 1934, 46, 618.
- (1934) Phys. Rev. , vol.46 , pp. 618
- Møller, C.¹ Plesset, M.S.²

28
- 0000189651
- A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
- (1993) J. Chem. Phys. , vol.98 , pp. 5648
- Becke, A.D.¹

29
- 0011083273
- A. P. Scott, L. Radom, J. Phys. Chem. 1996, 100, 16502.
- (1996) J. Phys. Chem. , vol.100 , pp. 16502
- Scott, A.P.¹ Radom, L.²

30
- 0003768228
- Blackwell Scientific, Oxford
- R. G. Gilbert, S. C. Smith, Theory of Unimolecular and Recombination Reactions, Blackwell Scientific, Oxford, 1990.
- (1990) Theory of Unimolecular and Recombination Reactions
- Gilbert, R.G.¹ Smith, S.C.²

31
- 0004176618
- Wiley-Interscience, New York
- W. Forst, Theory of Unimolecular Reactions, Wiley-Interscience, New York, 1973.
- (1973) Theory of Unimolecular Reactions
- Forst, W.¹

32
- 0000880057
- B. D. Wladkowski, K. F. Lim, W. D. Allen, J. I. Brauman, J. Am. Chem. Soc. 1992, 114, 9136.
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 9136
- Wladkowski, B.D.¹ Lim, K.F.² Allen, W.D.³ Brauman, J.I.⁴

33
- 33847089629
- K. Hiraoka, P. Kebarle, J. Am. Chem. Soc. 1977, 99, 360.
- (1977) J. Am. Chem. Soc. , vol.99 , pp. 360
- Hiraoka, K.¹ Kebarle, P.²

34
- 33845375179
- K. Hiraoka, H. Takimoto, K. Morise, J. Am. Chem. Soc. 1985, 108, 5683.
- (1985) J. Am. Chem. Soc. , vol.108 , pp. 5683
- Hiraoka, K.¹ Takimoto, H.² Morise, K.³

35
- 33845470658
- K. Raghavachari, J. Chandrasekhar, R. C. Burnier, J. Am. Chem. Soc. 1984, 106, 3124.
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 3124
- Raghavachari, K.¹ Chandrasekhar, J.² Burnier, R.C.³

36
- 0001998551
- S. G. Lias, J. E. Bartmess, J. F. Liebman, J. H. Holmes, R. D. Levin, W. G. Mallard, J. Phys. Chem. Ref. Data 1988, 17, 1.
- (1988) J. Phys. Chem. Ref. Data , vol.17 , pp. 1
- Lias, S.G.¹ Bartmess, J.E.² Liebman, J.F.³ Holmes, J.H.⁴ Levin, R.D.⁵ Mallard, W.G.⁶

37
- 0141917879
- S. G. Lias, H. M. Rosenstock, K. Deard, B. W. Steiner, J. T. Herron, J. H. Holmes, R. D. Levin, J. F. Liebman, S. A. Kafafi, J. E. Bartmess, E. F. Hunter, NIST Chemistry Webbook (http://webbook.nist.goc/ chemistry), 1997.
- (1997) NIST Chemistry Webbook
- Lias, S.G.¹ Rosenstock, H.M.² Deard, K.³ Steiner, B.W.⁴ Herron, J.T.⁵ Holmes, J.H.⁶ Levin, R.D.⁷ Liebman, J.F.⁸ Kafafi, S.A.⁹ Bartmess, J.E.¹⁰ Hunter, E.F.¹¹

38
- 0021375586
- G. Caldwell, T. F. Magnera, P. Kebarle, J. Am. Chem. Soc. 1984, 106, 959.
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 959
- Caldwell, G.¹ Magnera, T.F.² Kebarle, P.³

39
- 0001343481
- C. DePuy, S. Gronert, A. Mullin, V. M. Bierbaum, J. Am. Chem. Soc. 1990, 112, 8650.
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 8650
- DePuy, C.¹ Gronert, S.² Mullin, A.³ Bierbaum, V.M.⁴

40
- 0000646874
- F. Jensen, Chem. Phys. Lett. 1992, 196, 368.
- (1992) Chem. Phys. Lett. , vol.196 , pp. 368
- Jensen, F.¹

41
- 0001768041
- S. Gronert, J. Am. Chem. Soc. 1993, 115, 652.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 652
- Gronert, S.¹

42
- 37049175995
- C. N. Hinshelwood, K. J. Laidler, E. W. Timm, J. Chem. Soc. 1938, 848.
- (1938) J. Chem. Soc. , vol.848
- Hinshelwood, C.N.¹ Laidler, K.J.² Timm, E.W.³

43
- 0348178420
- P. B. D. de la Mare, L. Fowden, E. D. Hughes, C. K. Ingold, J. D. H. Mackie, J. Chem. Soc. 1955, 3169.
- (1955) J. Chem. Soc. , pp. 3169
- De La Mare, P.B.D.¹ Fowden, L.² Hughes, E.D.³ Ingold, C.K.⁴ Mackie, J.D.H.⁵

44
- 0004159850
- McGraw-Hill, New York
- A. Streitwieser, Solvolytic Displacement Reactions, McGraw-Hill, New York, 1962.
- (1962) Solvolytic Displacement Reactions
- Streitwieser, A.¹

45
- 0346287676
- N. Ivanoff, M. Magat, J. Chim. Phys. 1950, 47, 914.
- (1950) J. Chim. Phys. , vol.47 , pp. 914
- Ivanoff, N.¹ Magat, M.²

46
- 0346917856
- E. Bauer, M. Magat, J. Chim. Phys. 1950, 47, 922.
- (1950) J. Chim. Phys. , vol.47 , pp. 922
- Bauer, E.¹ Magat, M.²

47
- 0006816363
- J. M. S. Henis, J. Am. Chem. Soc. 1968, 90, 844.
- (1968) J. Am. Chem. Soc. , vol.90 , pp. 844
- Henis, J.M.S.¹

48
- 0041332988
- J. L. Beauchamp, M. C. Caserio, J. Am. Chem. Soc. 1972, 94, 2638.
- (1972) J. Am. Chem. Soc. , vol.94 , pp. 2638
- Beauchamp, J.L.¹ Caserio, M.C.²

49
- 0000407032
- J. L. Beauchamp, M. C. Caserio, T. B. McMahon, J. Am. Chem. Soc. 1974, 96, 6243.
- (1974) J. Am. Chem. Soc. , vol.96 , pp. 6243
- Beauchamp, J.L.¹ Caserio, M.C.² McMahon, T.B.³

50
- 0001446848
- T. B. McMahon, J. L. Beauchamp, J. Phys. Chem. 1977, 81, 593.
- (1977) J. Phys. Chem. , vol.81 , pp. 593
- McMahon, T.B.¹ Beauchamp, J.L.²

51
- 0000864722
- Z. Karpas, M. Meot-Ner, J. Phys. Chem. 1989, 93, 1859.
- (1989) J. Phys. Chem. , vol.93 , pp. 1859
- Karpas, Z.¹ Meot-Ner, M.²

52
- 0020844876
- L. M. Bass, R. D. Cates, M. F. Jarrold, N. J. Kirchner, M. T. Bowers, J. Am. Chem. Soc. 1983, 105, 7024.
- (1983) J. Am. Chem. Soc. , vol.105 , pp. 7024
- Bass, L.M.¹ Cates, R.D.² Jarrold, M.F.³ Kirchner, N.J.⁴ Bowers, M.T.⁵

53
- 84989064963
- J. C. Kleingeld, N. N. M. Nibbering, Org. Mass Spectrom. 1982, 17, 136.
- (1982) Org. Mass Spectrom. , vol.17 , pp. 136
- Kleingeld, J.C.¹ Nibbering, N.N.M.²

54
- 37049067871
- J. C. Sheldon, G. J. Currie, J. H. Bowie, J. Chem. Soc. Perkin Trans. II 1986, 941.
- (1986) J. Chem. Soc. Perkin Trans. II , pp. 941
- Sheldon, J.C.¹ Currie, G.J.² Bowie, J.H.³

55
- 33845556977
- D. G. Hall, C. Gupta, T. H. Morton, J. Am. Chem. Soc. 1981, 103, 2416.
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 2416
- Hall, D.G.¹ Gupta, C.² Morton, T.H.³

56
- 0346287675
- T. H. Morton, Tetrahedron 1982, 38, 3213.
- (1982) Tetrahedron , vol.38 , pp. 3213
- Morton, T.H.¹

57
- 0001884616
- D. Berthomieu, H. Audier, Eur. Mass Spectrom. 1997, 3, 19.
- (1997) Eur. Mass Spectrom. , vol.3 , pp. 19
- Berthomieu, D.¹ Audier, H.²

58
- 84943914342
- R. G. Keese, A. W. Castleman, J. Phys. Chem. Ref. Data 1985, 15, 1011.
- (1985) J. Phys. Chem. Ref. Data , vol.15 , pp. 1011
- Keese, R.G.¹ Castleman, A.W.²

59
- 0004244010
- Oxford University Press, Oxford
- D. F. Shriver, P. W. Atkins, C. P. Langford, Inorganic Chemistry, Oxford University Press, Oxford, 1990.
- (1990) Inorganic Chemistry
- Shriver, D.F.¹ Atkins, P.W.² Langford, C.P.³

60
- 0001364768
- E. Uggerud, J. Am. Chem. Soc. 1994, 116, 6873.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 6873
- Uggerud, E.¹

61
- 0000127210
- G. Bouchoux, Y. Hoppilliard, J. Am. Chem. Soc. 1990, 112, 9110.
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 9110
- Bouchoux, G.¹ Hoppilliard, Y.²

62
- 84989012110
- D. J. Swanton, D. C. J. Marsden, L. Radom, Org. Mass Spectrom. 1991, 26, 227.
- (1991) Org. Mass Spectrom. , vol.26 , pp. 227
- Swanton, D.J.¹ Marsden, D.C.J.² Radom, L.³

63
- 0004258726
- Chapman and Hall, London
- R. P. Bell, The Proton in Chemistry, Chapman and Hall, London, 1973.
- (1973) The Proton in Chemistry
- Bell, R.P.¹

64
- 0008028137
- M. Meot-Ner, J. Am. Chem. Soc. 1984, 106, 1257.
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 1257
- Meot-Ner, M.¹

65
- 0001363625
- W. R. Davidson, J. Sunner, P. Kebarle, J. Am. Chem. Soc. 1979, 101, 1675.
- (1979) J. Am. Chem. Soc. , vol.101 , pp. 1675
- Davidson, W.R.¹ Sunner, J.² Kebarle, P.³

66
- 33947297370
- E. V. Waage, B. S. Rabinovitch, Chem. Rev. 1970, 70, 377.
- (1970) Chem. Rev. , vol.70 , pp. 377
- Waage, E.V.¹ Rabinovitch, B.S.²

67
- 0542382495
- M. W. Wong, M. J. Frisch, K. B. Wiberg, J. Am. Chem. Soc. 1991, 113, 4776.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 4776
- Wong, M.W.¹ Frisch, M.J.² Wiberg, K.B.³

68
- 37049170377
- I. Dostrovsky, F. S. Klein, J. Chem. Soc. 1955, 791.
- (1955) J. Chem. Soc. , pp. 791
- Dostrovsky, I.¹ Klein, F.S.²

69
- 0003698548
- (Ed.: M. T. Bowers), Academic Press, New York
- J. E. Bartmess, J. R. T. McIver, in Gas Phase Ion Chemistry, Vol. 2, (Ed.: M. T. Bowers), Academic Press, New York, 1979.
- (1979) Gas Phase Ion Chemistry, Vol. 2 , vol.2
- Bartmess, J.E.¹ McIver, J.R.T.²

70
- 33947294759
- J. L. Brauman, L. K. Blair, J. Am. Chem. Soc. 1970, 92, 5986.
- (1970) J. Am. Chem. Soc. , vol.92 , pp. 5986
- Brauman, J.L.¹ Blair, L.K.²

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