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Volumn 62, Issue 17, 1997, Pages 5811-5820

Isolation and Structure Elucidation of Transient (Colored) Complexes of Arenediazonium with Aromatic Hydrocarbons as Intermediates in Arylations and Azo Couplings

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EID: 0000762877     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970540n     Document Type: Article
Times cited : (29)

References (96)
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    • .+ For a recent summary of the experimental verification of charge transfer activation by time-resolved spectroscopy, see ref 7.
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    • The crystallization problem is exacerbated by the grossly dissimilar solubilities of the components, such as the hydrophilic diazonium salt in strong contrast to hydrophobic (uncharged) aromatic donor
    • The crystallization problem is exacerbated by the grossly dissimilar solubilities of the components, such as the hydrophilic diazonium salt in strong contrast to hydrophobic (uncharged) aromatic donor.
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    • + allowed their ready resolution from those of ArH, sufficient to clearly establish the molecular ratios extant in the crystalline EDA complexes.
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    • For the exception, see the CT crystal of p-xylene/p-carbethoxybenzenediazonium hexafluorophosphate in which crystallization in the presence of excess p-xylene led to the 2A·D complex, whereas crystallization with a tenfold excess of diazonium salt led to the 4A·D stoichiometry.
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    • Crystalline complexes were not observed with this acceptor and either benzene or mesitylene. For the crystallographic explanation of the phenomenon, see Lindeman, S. V. in ref 45b.
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    • m-Nitrobenzenediazonium also formed crystalline complexes with p-dimethoxybenzene, but they were not analyzed further
    • m-Nitrobenzenediazonium also formed crystalline complexes with p-dimethoxybenzene, but they were not analyzed further.
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    • University Chemical Lab, Lensfield Rd, Cambridge CB2 1EW, United Kingdom
    • University Chemical Lab, Lensfield Rd, Cambridge CB2 1EW, United Kingdom.
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    • Such deformations are common to all diazonium cations whose structures have been crystallographically determined. See: (a) Sorriso, S. in ref 1, p 95. (b) Ball, R. G.; Elofson, R. M. Can. J. Chem. 1985, 63, 332. (c) Barnes, J. C.; Butler, A.; Anderson, L. Acta Crystallogr. 1990, C46, 945, (d) Horan, C. J.; Barnes, C. L.; Glaser, R. Acta Crystallogr. 1993, C49, 507. (e) Alcock, N. W.; Greenhough, T. J.; Hirst, D. M.; Kemp, T. J.; Payne, D. R. J. Chem. Soc., Perkin Trans. 2 1980, 8. (f) Sasvari, K.; Hess, H.; Schwarz, W. Cryst. Struct, Commun. 1982, 11, 781. (g) Cygler, M. et al. in ref 9.
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    • Such deformations are common to all diazonium cations whose structures have been crystallographically determined. See: (a) Sorriso, S. in ref 1, p 95. (b) Ball, R. G.; Elofson, R. M. Can. J. Chem. 1985, 63, 332. (c) Barnes, J. C.; Butler, A.; Anderson, L. Acta Crystallogr. 1990, C46, 945, (d) Horan, C. J.; Barnes, C. L.; Glaser, R. Acta Crystallogr. 1993, C49, 507. (e) Alcock, N. W.; Greenhough, T. J.; Hirst, D. M.; Kemp, T. J.; Payne, D. R. J. Chem. Soc., Perkin Trans. 2 1980, 8. (f) Sasvari, K.; Hess, H.; Schwarz, W. Cryst. Struct, Commun. 1982, 11, 781. (g) Cygler, M. et al. in ref 9.
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    • Such deformations are common to all diazonium cations whose structures have been crystallographically determined. See: (a) Sorriso, S. in ref 1, p 95. (b) Ball, R. G.; Elofson, R. M. Can. J. Chem. 1985, 63, 332. (c) Barnes, J. C.; Butler, A.; Anderson, L. Acta Crystallogr. 1990, C46, 945, (d) Horan, C. J.; Barnes, C. L.; Glaser, R. Acta Crystallogr. 1993, C49, 507. (e) Alcock, N. W.; Greenhough, T. J.; Hirst, D. M.; Kemp, T. J.; Payne, D. R. J. Chem. Soc., Perkin Trans. 2 1980, 8. (f) Sasvari, K.; Hess, H.; Schwarz, W. Cryst. Struct, Commun. 1982, 11, 781. (g) Cygler, M. et al. in ref 9.
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    • Such deformations are common to all diazonium cations whose structures have been crystallographically determined. See: (a) Sorriso, S. in ref 1, p 95. (b) Ball, R. G.; Elofson, R. M. Can. J. Chem. 1985, 63, 332. (c) Barnes, J. C.; Butler, A.; Anderson, L. Acta Crystallogr. 1990, C46, 945, (d) Horan, C. J.; Barnes, C. L.; Glaser, R. Acta Crystallogr. 1993, C49, 507. (e) Alcock, N. W.; Greenhough, T. J.; Hirst, D. M.; Kemp, T. J.; Payne, D. R. J. Chem. Soc., Perkin Trans. 2 1980, 8. (f) Sasvari, K.; Hess, H.; Schwarz, W. Cryst. Struct, Commun. 1982, 11, 781. (g) Cygler, M. et al. in ref 9.
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    • Such deformations are common to all diazonium cations whose structures have been crystallographically determined. See: (a) Sorriso, S. in ref 1, p 95. (b) Ball, R. G.; Elofson, R. M. Can. J. Chem. 1985, 63, 332. (c) Barnes, J. C.; Butler, A.; Anderson, L. Acta Crystallogr. 1990, C46, 945, (d) Horan, C. J.; Barnes, C. L.; Glaser, R. Acta Crystallogr. 1993, C49, 507. (e) Alcock, N. W.; Greenhough, T. J.; Hirst, D. M.; Kemp, T. J.; Payne, D. R. J. Chem. Soc., Perkin Trans. 2 1980, 8. (f) Sasvari, K.; Hess, H.; Schwarz, W. Cryst. Struct, Commun. 1982, 11, 781. (g) Cygler, M. et al. in ref 9.
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    • Such deformations are common to all diazonium cations whose structures have been crystallographically determined. See: (a) Sorriso, S. in ref 1, p 95. (b) Ball, R. G.; Elofson, R. M. Can. J. Chem. 1985, 63, 332. (c) Barnes, J. C.; Butler, A.; Anderson, L. Acta Crystallogr. 1990, C46, 945, (d) Horan, C. J.; Barnes, C. L.; Glaser, R. Acta Crystallogr. 1993, C49, 507. (e) Alcock, N. W.; Greenhough, T. J.; Hirst, D. M.; Kemp, T. J.; Payne, D. R. J. Chem. Soc., Perkin Trans. 2 1980, 8. (f) Sasvari, K.; Hess, H.; Schwarz, W. Cryst. Struct, Commun. 1982, 11, 781. (g) Cygler, M. et al. in ref 9.
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    • in ref 9
    • Such deformations are common to all diazonium cations whose structures have been crystallographically determined. See: (a) Sorriso, S. in ref 1, p 95. (b) Ball, R. G.; Elofson, R. M. Can. J. Chem. 1985, 63, 332. (c) Barnes, J. C.; Butler, A.; Anderson, L. Acta Crystallogr. 1990, C46, 945, (d) Horan, C. J.; Barnes, C. L.; Glaser, R. Acta Crystallogr. 1993, C49, 507. (e) Alcock, N. W.; Greenhough, T. J.; Hirst, D. M.; Kemp, T. J.; Payne, D. R. J. Chem. Soc., Perkin Trans. 2 1980, 8. (f) Sasvari, K.; Hess, H.; Schwarz, W. Cryst. Struct, Commun. 1982, 11, 781. (g) Cygler, M. et al. in ref 9.
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    • See also ref 41b
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    • note
    • Otherwise, the X-ray crystallography does not distinguish the donor-acceptor interactions extant in the carbethoxybenzenediazonium EDA complexes from those involving the strongest acceptor (i.e., the 3,5-dinitro analogue). However, we note that the aromatic donors are crystallographically disordered in the carbethoxydiazonium crystals whereas they are essentially not disordered in the dinitrodiazonium crystals. The latter suggests that the intermolecular forces are stronger in the CT crystals of the stronger acceptor.
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    • - network,
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    • manuscript to be submitted
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    • Small lateral displacements along the aromatic planes are not expected to be important factors in the charge-transfer transitions. See: (a) Staab, H. A.; Reibel, W. R. K.; Krieger, C. Chem. Ber. 1985, 118, 1230. (b) Volger, H.; Schanne, L.; Staab, H. A. Chem. Ber. 1985, 118, 1254.
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    • Small lateral displacements along the aromatic planes are not expected to be important factors in the charge-transfer transitions. See: (a) Staab, H. A.; Reibel, W. R. K.; Krieger, C. Chem. Ber. 1985, 118, 1230. (b) Volger, H.; Schanne, L.; Staab, H. A. Chem. Ber. 1985, 118, 1254.
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    • See: (a) Galli, C. Chem. Rev. 1988, 88, 765. (b) Via the rapid homolysis of the aryldiazenyl radical, see: Suehiro, T. Rev. Chem. Intermed. 1988, 20, 101.
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    • See: (a) Galli, C. Chem. Rev. 1988, 88, 765. (b) Via the rapid homolysis of the aryldiazenyl radical, see: Suehiro, T. Rev. Chem. Intermed. 1988, 20, 101.
    • (1988) Rev. Chem. Intermed. , vol.20 , pp. 101
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