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Volumn 111, Issue 6, 1989, Pages 1968-1973

The Gas-Phase Acidities of the Alkanes

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EID: 0001013904     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00188a003     Document Type: Article
Times cited : (173)

References (25)
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    • Comprehensive Carbanion Chemistry
    • Part A; Buncel, E., Durst, T., Eds.; Elsevier: Amsterdam Chapter 7. (b) Streitwieser, A., Jr.; Taylor, D. R. J. Chem. Soc., Chem. Commun. 1970, 1248. (c) Dessy, R. E.; Kitching, W.; Psarras, T.; Salinger, R.; Chen, A.; Chivers, T. J. Am. Chem. Soc. 1966, 88, 460. (d) Applequist, D. E.; O'Brien, P. F. J. Am. Chem. Soc. 1963, 85, 743
    • (a) Streitwieser, A., Jr.; Juaristi, E.; Nebenzahl, L. L. In Comprehensive Carbanion Chemistry, Part A; Buncel, E., Durst, T., Eds.; Elsevier: Amsterdam, 1980; Chapter 7. (b) Streitwieser, A., Jr.; Taylor, D. R. J. Chem. Soc., Chem. Commun. 1970, 1248. (c) Dessy, R. E.; Kitching, W.; Psarras, T.; Salinger, R.; Chen, A.; Chivers, T. J. Am. Chem. Soc. 1966, 88, 460. (d) Applequist, D. E.; O'Brien, P. F. J. Am. Chem. Soc. 1963, 85, 743.
    • (1980)
    • Streitwieser, A.1    Juaristi, E.2    Nebenzahl, L.L.3
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    • (b) Schleyer, P. v. R.; Spitznagel, G. W.; Chandrasekhar, J. Tetrahedron Lett. 1986, 27, 4411. (c) Siggel, M. R.; Thomas, T. D.; Saethre, L. J. J. Am. Chem. Soc. 1988, 110, 91. (d) Jorgensen, W. L.; Briggs, J. M.; Gao, J. J. Am. Chem. Soc. 1987, 109, 6857
    • (a) Kollmar, H. J. Am. Chem. Soc. 1978, 100, 2665. (b) Schleyer, P. v. R.; Spitznagel, G. W.; Chandrasekhar, J. Tetrahedron Lett. 1986, 27, 4411. (c) Siggel, M. R.; Thomas, T. D.; Saethre, L. J. J. Am. Chem. Soc. 1988, 110, 91. (d) Jorgensen, W. L.; Briggs, J. M.; Gao, J. J. Am. Chem. Soc. 1987, 109, 6857.
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    • Kollmar, H.1
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    • A general treatment of both the computational and experimental aspects of siliconate formation has recently been published. Damrauer, R.; Burggraf, L. W.; Davis, L. P.; Gordon, M. S. J. Am. Chem. Soc. 1988, 110, 6601
    • DePuy, C. H.; Bierbaum, V. M.; Flippin, L. A.; Grabowski, J. J.; King, G. K.; Schmitt, R. J.; Sullivan, S. A. J. Am. Chem. Soc. 1980, 102, 5012. A general treatment of both the computational and experimental aspects of siliconate formation has recently been published. Damrauer, R.; Burggraf, L. W.; Davis, L. P.; Gordon, M. S. J. Am. Chem. Soc. 1988, 110, 6601.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 5012
    • DePuy, C.H.1    Bierbaum, V.M.2    Flippin, L.A.3    Grabowski, J.J.4    King, G.K.5    Schmitt, R.J.6    Sullivan, S.A.7
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    • The ease of silane cleavage with base in solution correlates with the basicity of the carbanion being expelled; see
    • The ease of silane cleavage with base in solution correlates with the basicity of the carbanion being expelled; see: Eaborn, C.; Walton, D. R. M. J. Chem. Soc., Chem. Commun. 1975, 937.
    • (1975) J. Chem. Soc., Chem. Commun. , pp. 937
    • Eaborn, C.1    Walton, D.R.M.2
  • 15
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    • This method of determining the relative basicities of ions is similar, in principle, to the method of Cooks and co-workers in which cluster ions are given internal energy by collisions in a mass spectrometer
    • This method of determining the relative basicities of ions is similar, in principle, to the method of Cooks and co-workers in which cluster ions are given internal energy by collisions in a mass spectrometer: Wright, L. G.; McLuckey, S. A.; Cooks, R. G.; Wood, K. V. Int. J. Mass Spectrom. Ion Phys. 1982, 42, 115.
    • (1982) Int. J. Mass Spectrom. Ion Phys. , vol.42 , pp. 115
    • Wright, L.G.1    McLuckey, S.A.2    Cooks, R.G.3    Wood, K.V.4
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    • University of Colorado at Boulder
    • Van Doren, J. M. Ph.D. Thesis, University of Colorado at Boulder, 1987.
    • (1987) Ph.D. Thesis
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    • University of Colorado at Boulder
    • Grabowski, J. J. Ph.D. Thesis, University of Colorado at Boulder, 1983.
    • (1983) Ph.D. Thesis
    • Grabowski, J.J.1
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    • We have carried out MM2 force field calculations on tert-butyltrimethylsilane using the recently published parameters that have been extended to silicon (Frierson, M. R.; Imam, M. R.; Zalkow, V. B.; Allinger, N. L. J. Org. Chem. 1988, 53, 5248). We found that tert-butyltrimethylsilane is strain free
    • Ouellette, R. J.; Baron, D.; Stolfo, J.; Rosenblum, A.; Weber, P. Tetrahedron 1972, 28, 2163. We have carried out MM2 force field calculations on tert-butyltrimethylsilane using the recently published parameters that have been extended to silicon (Frierson, M. R.; Imam, M. R.; Zalkow, V. B.; Allinger, N. L. J. Org. Chem. 1988, 53, 5248). We found that tert-butyltrimethylsilane is strain free.
    • (1972) Tetrahedron , vol.28 , pp. 2163
    • Ouellette, R.J.1    Baron, D.2    Stolfo, J.3    Rosenblum, A.4    Weber, P.5
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    • in press For other recent studies of bond dissociation energies see: Russell, J. J.; Seetula, J. A.; Gutman, D. J. Am. Chem. Soc. 1988, 110, 3092. Russell, J. J.; Seetula, J. A.; Timonen, R. S.; Gutman, D.; Nava, D. F. J. Am. Chem. Soc. 1988, 110, 3084
    • Griller, D.; Kanabus-Kaminska, J. M.; Maccoll, A. J. Mol. Struct., in press. For other recent studies of bond dissociation energies see: Russell, J. J.; Seetula, J. A.; Gutman, D. J. Am. Chem. Soc. 1988, 110, 3092. Russell, J. J.; Seetula, J. A.; Timonen, R. S.; Gutman, D.; Nava, D. F. J. Am. Chem. Soc. 1988, 110, 3084.
    • J. Mol. Struct.
    • Griller, D.1    Kanabus-Kaminska, J.M.2    Maccoll, A.3


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