-
4
-
-
0000045352
-
-
+ estimated to be at least 0.8 V. See Elofson, R. M.; Gadallah, F. F. J. Org, Chem. 1969, 34, 854.
-
(1969)
J. Org, Chem.
, vol.34
, pp. 854
-
-
Elofson, R.M.1
Gadallah, F.F.2
-
5
-
-
85033127432
-
-
p = 1.91
-
p = 1.91.
-
-
-
-
8
-
-
0006088262
-
-
(b) Colter, A. K.; Dack, M. R. J., Mol. Complex. 1973, 1, 301; 1974, 2, 1.
-
(1973)
Mol. Complex.
, vol.1
, pp. 301
-
-
Colter, A.K.1
Dack, M.R.J.2
-
9
-
-
1542746883
-
-
(b) Colter, A. K.; Dack, M. R. J., Mol. Complex. 1973, 1, 301; 1974, 2, 1.
-
(1974)
Mol. Complex.
, vol.2
, pp. 1
-
-
-
12
-
-
0542371080
-
-
A is the perspective view of the EDA complex of p-methoxybenzenediazonium tetrafluoroborate and 21- crown-7. (The p-methoxy group is deleted for clarity). Groth, P. Acta Chem. Scand. 1981, A35, 541.
-
(1981)
Acta Chem. Scand.
, vol.A35
, pp. 541
-
-
Groth, P.1
-
13
-
-
0001185652
-
-
Cygler, M.; Przybylska, M.; Elofson, R. M. Can. J. Chem. 1982, 60, 2852.
-
(1982)
Can. J. Chem.
, vol.60
, pp. 2852
-
-
Cygler, M.1
Przybylska, M.2
Elofson, R.M.3
-
16
-
-
0005988533
-
-
(b) Kim, G. C. Y.; Batchelor, F. J.; Yan, X.; Einstein, F. W. B.; Sutton, D. Inorg. Chem. 1995, 34, 6163.
-
(1995)
Inorg. Chem.
, vol.34
, pp. 6163
-
-
Kim, G.C.Y.1
Batchelor, F.J.2
Yan, X.3
Einstein, F.W.B.4
Sutton, D.5
-
18
-
-
84987592645
-
-
For a discussion of which nitrogen is the center of cationic charge, see Wallis, J. D.; Easton, R. J. C.; Dunitz, J. D. Helv. Chim. Acta 1993, 76, 1411.
-
(1993)
Helv. Chim. Acta
, vol.76
, pp. 1411
-
-
Wallis, J.D.1
Easton, R.J.C.2
Dunitz, J.D.3
-
20
-
-
1542536677
-
-
Kampar, V. E.; Kokars, V. R.; Neiland, O. Ya. Zhur. Obs. Khim. [Engl. Trans]. 1977, 47, 784.
-
(1977)
Zhur. Obs. Khim. [Engl. Trans].
, vol.47
, pp. 784
-
-
Kampar, V.E.1
Kokars, V.R.2
Neiland, O.Ya.3
-
21
-
-
0347197590
-
-
+ with anionic donors, see Becker, H. G. O.; Schukat, G.; Kuzmin, M. G. J. Prakt. Chem. 1975, 317, 229. Jirksky, J.; Fojtik, A.; Becker, H. G. O. Coll. Czech. Chem. Commun. 1981, 46, 1560. Becker, H. G. O.; Pfeifer, D.; Radeglia, R. Z. Naturforsch. 1983, 386, 1591.
-
(1975)
J. Prakt. Chem.
, vol.317
, pp. 229
-
-
Becker, H.G.O.1
Schukat, G.2
Kuzmin, M.G.3
-
22
-
-
0000624931
-
-
+ with anionic donors, see Becker, H. G. O.; Schukat, G.; Kuzmin, M. G. J. Prakt. Chem. 1975, 317, 229. Jirksky, J.; Fojtik, A.; Becker, H. G. O. Coll. Czech. Chem. Commun. 1981, 46, 1560. Becker, H. G. O.; Pfeifer, D.; Radeglia, R. Z. Naturforsch. 1983, 386, 1591.
-
(1981)
Coll. Czech. Chem. Commun.
, vol.46
, pp. 1560
-
-
Jirksky, J.1
Fojtik, A.2
Becker, H.G.O.3
-
23
-
-
84912757478
-
-
+ with anionic donors, see Becker, H. G. O.; Schukat, G.; Kuzmin, M. G. J. Prakt. Chem. 1975, 317, 229. Jirksky, J.; Fojtik, A.; Becker, H. G. O. Coll. Czech. Chem. Commun. 1981, 46, 1560. Becker, H. G. O.; Pfeifer, D.; Radeglia, R. Z. Naturforsch. 1983, 386, 1591.
-
(1983)
Z. Naturforsch.
, vol.386
, pp. 1591
-
-
Becker, H.G.O.1
Pfeifer, D.2
Radeglia, R.3
-
25
-
-
85033145116
-
-
in ref 1, p 232 ff
-
For reviews, see Niemeyer, H. M. in ref 1, p 232 ff and Lewis, E. S. in ref 1, p 506.
-
-
-
Niemeyer, H.M.1
-
26
-
-
85033158536
-
-
in ref 1, p 506
-
For reviews, see Niemeyer, H. M. in ref 1, p 232 ff and Lewis, E. S. in ref 1, p 506.
-
-
-
Lewis, E.S.1
-
28
-
-
85033148776
-
-
in ref 1, p 645
-
Shank, K. in ref 1, p 645.
-
-
-
Shank, K.1
-
29
-
-
85033137773
-
-
in ref 3, p 671
-
March, J. in ref 3, p 671.
-
-
-
March, J.1
-
31
-
-
0004033856
-
-
Halsted Press: New York
-
(b) Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki T.; Iwata, S. Handbook of HeI Photoelectron Spectra of Fundamental Organic Molecules; Halsted Press: New York, 1981.
-
(1981)
Handbook of HeI Photoelectron Spectra of Fundamental Organic Molecules
-
-
Kimura, K.1
Katsumata, S.2
Achiba, Y.3
Yamazaki, T.4
Iwata, S.5
-
33
-
-
0021456218
-
-
See also Howell, J. O.; Goncalves, J. M.; Amatore, C.; Klasinc, L.; Wightman, R. M.; Kochi, J. K. J. Am. Chem. Soc. 1984, 106, 3968.
-
(1984)
J. Am. Chem. Soc.
, vol.106
, pp. 3968
-
-
Howell, J.O.1
Goncalves, J.M.2
Amatore, C.3
Klasinc, L.4
Wightman, R.M.5
Kochi, J.K.6
-
36
-
-
0004079376
-
-
Foster, R., Ed.; Crane, Russak: New York, p 2 ff.
-
Hanna, M. W.; Lippert, J. L. In Molecular Complexes; Foster, R., Ed.; Crane, Russak: New York, 1973; Vol. 1, p 2 ff.
-
(1973)
Molecular Complexes
, vol.1
-
-
Hanna, M.W.1
Lippert, J.L.2
-
37
-
-
85033147129
-
-
note
-
.+ For a recent summary of the experimental verification of charge transfer activation by time-resolved spectroscopy, see ref 7.
-
-
-
-
43
-
-
85033158125
-
-
note
-
EDA is insufficient to establish structural relationships with certainty.
-
-
-
-
44
-
-
85033157278
-
-
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.
-
-
-
-
45
-
-
85033131277
-
-
note
-
+ allowed their ready resolution from those of ArH, sufficient to clearly establish the molecular ratios extant in the crystalline EDA complexes.
-
-
-
-
46
-
-
85033151696
-
-
note
-
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.
-
-
-
-
47
-
-
85033143431
-
-
in ref 45b
-
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.
-
-
-
Lindeman, S.V.1
-
48
-
-
85033147581
-
-
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.
-
-
-
-
49
-
-
85033135846
-
-
University Chemical Lab, Lensfield Rd, Cambridge CB2 1EW, United Kingdom
-
University Chemical Lab, Lensfield Rd, Cambridge CB2 1EW, United Kingdom.
-
-
-
-
50
-
-
85033133971
-
-
note
-
45b
-
-
-
-
51
-
-
85033142797
-
-
in ref 1, p 95
-
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.
-
-
-
Sorriso, S.1
-
52
-
-
1542536660
-
-
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.
-
(1985)
Can. J. Chem.
, vol.63
, pp. 332
-
-
Ball, R.G.1
Elofson, R.M.2
-
53
-
-
0005681193
-
-
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.
-
(1990)
Acta Crystallogr.
, vol.C46
, pp. 945
-
-
Barnes, J.C.1
Butler, A.2
Anderson, L.3
-
54
-
-
84983168521
-
-
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.
-
(1993)
Acta Crystallogr.
, vol.C49
, pp. 507
-
-
Horan, C.J.1
Barnes, C.L.2
Glaser, R.3
-
55
-
-
37049104872
-
-
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.
-
(1980)
J. Chem. Soc., Perkin Trans. 2
, pp. 8
-
-
Alcock, N.W.1
Greenhough, T.J.2
Hirst, D.M.3
Kemp, T.J.4
Payne, D.R.5
-
56
-
-
0005733738
-
-
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.
-
(1982)
Cryst. Struct, Commun.
, vol.11
, pp. 781
-
-
Sasvari, K.1
Hess, H.2
Schwarz, W.3
-
57
-
-
85033139316
-
-
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.
-
-
-
Cygler, M.1
-
60
-
-
0002089940
-
-
(a) Bacon, G. E.; Curry, N. A.; Wilson, S. A. Proc. Roy. Soc. London, Ser. A 1964, 279, 98.
-
(1964)
Proc. Roy. Soc. London, Ser. A
, vol.279
, pp. 98
-
-
Bacon, G.E.1
Curry, N.A.2
Wilson, S.A.3
-
62
-
-
0002990550
-
-
Allen, F. H.; Kinnard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. G. J. Chem. Soc., Perkin Trans. 2 1987, 51.
-
(1987)
J. Chem. Soc., Perkin Trans. 2
, pp. 51
-
-
Allen, F.H.1
Kinnard, O.2
Watson, D.G.3
Brammer, L.4
Orpen, A.G.5
Taylor, R.G.6
-
64
-
-
0000088996
-
-
See also ref 41b
-
(b) Iball, J.; Low, J. N. Acta Cryst. 1974, B30, 2203. See also ref 41b.
-
(1974)
Acta Cryst.
, vol.B30
, pp. 2203
-
-
Iball, J.1
Low, J.N.2
-
65
-
-
0346453860
-
-
(a) Gerzain, M.; Buchanan, G. W.; Driega, A. B.; Facey, G. A.; Enright, G.; Kirby, R. A. J. Chem. Soc., Perkin Trans. 2 1996, 2687.
-
(1996)
J. Chem. Soc., Perkin Trans. 2
, pp. 2687
-
-
Gerzain, M.1
Buchanan, G.W.2
Driega, A.B.3
Facey, G.A.4
Enright, G.5
Kirby, R.A.6
-
67
-
-
85033158593
-
-
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.
-
-
-
-
69
-
-
0001692003
-
-
Takahashi, Y.; Sankararaman, S.; Kochi, J. K. J. Am. Chem. Soc. 1989, 111, 2954.
-
(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 2954
-
-
Takahashi, Y.1
Sankararaman, S.2
Kochi, J.K.3
-
70
-
-
85033152906
-
-
note
-
- network,
-
-
-
-
71
-
-
85033153495
-
-
manuscript to be submitted
-
(b) Lindeman, S. V., manuscript to be submitted.
-
-
-
Lindeman, S.V.1
-
72
-
-
0000366992
-
-
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.
-
(1985)
Chem. Ber.
, vol.118
, pp. 1230
-
-
Staab, H.A.1
Reibel, W.R.K.2
Krieger, C.3
-
73
-
-
0345983856
-
-
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.
-
(1985)
Chem. Ber.
, vol.118
, pp. 1254
-
-
Volger, H.1
Schanne, L.2
Staab, H.A.3
-
74
-
-
33751154708
-
-
+ onto the aromatic moiety is in line with electron-density calculations. See: Glaser, R.; Horan, C. J. J. Org. Chem. 1995, 60, 7518.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 7518
-
-
Glaser, R.1
Horan, C.J.2
-
78
-
-
0001358527
-
-
(b) Cohen, T.; Lewarchik, R. J.; Tarino, J. Z. J. Am. Chem. Soc. 1974, 96, 7753. Rondestvedt, C. S. Org. React. 1960, 11, 189.
-
(1974)
J. Am. Chem. Soc.
, vol.96
, pp. 7753
-
-
Cohen, T.1
Lewarchik, R.J.2
Tarino, J.Z.3
-
79
-
-
0001358527
-
-
(b) Cohen, T.; Lewarchik, R. J.; Tarino, J. Z. J. Am. Chem. Soc. 1974, 96, 7753. Rondestvedt, C. S. Org. React. 1960, 11, 189.
-
(1960)
Org. React.
, vol.11
, pp. 189
-
-
Rondestvedt, C.S.1
-
85
-
-
2942545129
-
-
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)
Chem. Rev.
, vol.88
, pp. 765
-
-
Galli, C.1
-
86
-
-
53749104557
-
-
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
-
-
Suehiro, T.1
-
87
-
-
0031007139
-
-
Kosynkin, D.; Bockman, T. M.; Kochi, J. K. J. Am. Chem. Soc. 1997, 119, 4846.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 4846
-
-
Kosynkin, D.1
Bockman, T.M.2
Kochi, J.K.3
-
89
-
-
85033140705
-
-
note
-
45b
-
-
-
-
92
-
-
0001244181
-
-
Hoshida, Y.; Ishida, H.; Sekiguchi, S.; Matsui, K. Bull. Chem. Soc. Jpn. 1974, 47, 1224.
-
(1974)
Bull. Chem. Soc. Jpn.
, vol.47
, pp. 1224
-
-
Hoshida, Y.1
Ishida, H.2
Sekiguchi, S.3
Matsui, K.4
-
93
-
-
0001577133
-
-
Carlson, B. A.; Sheppard, W. A.; Webster, O. W. J. Am. Chem. Soc. 1975, 97, 5291.
-
(1975)
J. Am. Chem. Soc.
, vol.97
, pp. 5291
-
-
Carlson, B.A.1
Sheppard, W.A.2
Webster, O.W.3
-
94
-
-
0017226845
-
-
Boots, S. G.; Franklin, M. A.; Dunlavey, B.; Costello, J.; Lipsitz, C.; Boots, M. R.; Rogers, K. S. Proc. Soc. Exp. Biol. Med. 1976, 151, 316.
-
(1976)
Proc. Soc. Exp. Biol. Med.
, vol.151
, pp. 316
-
-
Boots, S.G.1
Franklin, M.A.2
Dunlavey, B.3
Costello, J.4
Lipsitz, C.5
Boots, M.R.6
Rogers, K.S.7
-
95
-
-
0020513843
-
-
Hermecz, I.; Breining, T.; Meszaros, Z.; Kokosi, J.; Meszaros, L.; Dessy, F.; De Vos, C. J. Med. Chem. 1983, 26, 1126.
-
(1983)
J. Med. Chem.
, vol.26
, pp. 1126
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Hermecz, I.1
Breining, T.2
Meszaros, Z.3
Kokosi, J.4
Meszaros, L.5
Dessy, F.6
De Vos, C.7
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