-
1
-
-
32144434172
-
-
ASAP, DOI: 10.1021/jo051746o
-
A. Stanger, J. Org. Chem. 2005, ASAP, DOI: 10.1021/jo051746o.
-
(2005)
J. Org. Chem.
-
-
Stanger, A.1
-
2
-
-
0011190497
-
-
Nucleus-independent chemical shift, see: P. von R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. van Eikema Hommes, J. Am. Chem. Soc. 1996, 118, 6317.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 6317
-
-
Von Schleyer, P.R.1
Maerker, C.2
Dransfeld, A.3
Jiao, H.4
Van Eikema Hommes, N.J.R.5
-
3
-
-
33645284511
-
-
note
-
The probe for the NICS calculations is a ghost atom which is called "bq" in the Gaussian package after Banquo, the ghost that hunts Macbeth. This naming will be used throughout the paper.
-
-
-
-
4
-
-
0042888578
-
-
For criticism of the RCM (ring current model), see: a) P. von R. Schleyer, M. Manoharan, Z.-X. Wang, B. Kiran, H. Jiao, R. Puchta, N. J. R. van Eikema Hommes, Org. Lett. 2001, 3, 2465.
-
(2001)
Org. Lett.
, vol.3
, pp. 2465
-
-
Von Schleyer, P.R.1
Manoharan, M.2
Wang, Z.-X.3
Kiran, B.4
Jiao, H.5
Puchta, R.6
Van Eikema Hommes, N.J.R.7
-
5
-
-
3142716769
-
-
For support of the RCM model (and criticism of the above-mentioned paper), see: b) R. G. Viglione, R. Zanasi, Org. Lett. 2004, 6, 2265.
-
(2004)
Org. Lett.
, vol.6
, pp. 2265
-
-
Viglione, R.G.1
Zanasi, R.2
-
6
-
-
33645327216
-
-
Chemical shifts taken from the SDBS (Spectral Database for Organic Compounds)
-
Chemical shifts taken from the SDBS (Spectral Database for Organic Compounds): http://www.aist.go.jp/RIODB/SDBS/menu-e.html.
-
-
-
-
9
-
-
0142043050
-
-
See, for example: S. J. Getty, D. A. Hrovat, J. Dong Xu, S. A. Barker. W. T. Borden, J. Chem. Soc. Faraday Trans. 1994, 90, 1689.
-
(1994)
J. Chem. Soc. Faraday Trans.
, vol.90
, pp. 1689
-
-
Getty, S.J.1
Hrovat, D.A.2
Dong Xu, J.3
Barker, S.A.4
Borden, W.T.5
-
10
-
-
33645291587
-
-
note
-
NICS(1) is the Isotropic nucleus-independent chemical-shift value (ppm) which is calculated 1 Å above the center of the molecular plane.
-
-
-
-
12
-
-
33645321933
-
-
note
-
3Sn, δ = 6.50 ppm;
-
-
-
-
13
-
-
2942735220
-
-
3Si, δ = 6.56 ppm, see: J. Čermák, L. Št'astná, J. Sýkora, J. Kvičala, Organometallics 2004, 23, 2850;
-
(2004)
Organometallics
, vol.23
, pp. 2850
-
-
Čermák, J.1
Št'Astná, L.2
Sýkora, J.3
Kvičala, J.4
-
14
-
-
0012220945
-
-
3Si, δ = 6.53-6.58 ppm, see: A. Klipp, S. H. A. Petri, B. Neumann, H.-G. Stammler, P. Jutzi, J. Organomet. Chem. 2001, 620, 20;
-
(2001)
J. Organomet. Chem.
, vol.620
, pp. 20
-
-
Klipp, A.1
Petri, S.H.A.2
Neumann, B.3
Stammler, H.-G.4
Jutzi, P.5
-
15
-
-
33645316172
-
-
note
-
3, δ = 5.94 ppm;
-
-
-
-
16
-
-
33645286578
-
-
note
-
2SiOMe, δ = 6.5 ppm;
-
-
-
-
17
-
-
0000470281
-
-
2SiCl, δ = 6.75 ppm, see: P. Jutzi, M. Schneider, H.-G. Stammler, B. Neumann, Organometallics 1997, 16, 5377;
-
(1997)
Organometallics
, vol.16
, pp. 5377
-
-
Jutzi, P.1
Schneider, M.2
Stammler, H.-G.3
Neumann, B.4
-
18
-
-
33645280417
-
-
note
-
3Ge, δ = 6.35 ppm;
-
-
-
-
19
-
-
33645319542
-
-
note
-
3Si, δ = 6.65 ppm;
-
-
-
-
20
-
-
0345987237
-
-
2GeCl, δ = 6.15, see: J. M. Rozell, Jr., P. R. Jones, Organometallics 1985, 4, 2206;
-
(1985)
Organometallics
, vol.4
, pp. 2206
-
-
Rozell Jr., J.M.1
Jones, P.R.2
-
21
-
-
33645300161
-
-
note
-
3Si, δ = 6.3 ppm;
-
-
-
-
22
-
-
0007941032
-
-
3Si, δ = 6.4 ppm, see: P. R. Jones, J. M. Rozell, Jr., B. M. Campbell, Organometallics 1985, 4, 1321.
-
(1985)
Organometallics
, vol.4
, pp. 1321
-
-
Jones, P.R.1
Rozell Jr., J.M.2
Campbell, B.M.3
-
23
-
-
6344261884
-
-
Recently, there have been reports about the NICS being inconsistent with other indices of aromaticity. See, for example: a) J. Poater, M. Solá, R. G. Viglione, R. Zanasi, J. Org. Chem. 2004, 69, 7537;
-
(2004)
J. Org. Chem.
, vol.69
, pp. 7537
-
-
Poater, J.1
Solá, M.2
Viglione, R.G.3
Zanasi, R.4
-
24
-
-
23944454338
-
-
b) F. Faglioni, A. Ligabue, S. Pelloni, A. Soncini, R. G. Viglione, M. B. Ferraro, R. Zanasi, P. Lazzeretti, Org. Lett. 2005, 7, 3457;
-
(2005)
Org. Lett.
, vol.7
, pp. 3457
-
-
Faglioni, F.1
Ligabue, A.2
Pelloni, S.3
Soncini, A.4
Viglione, R.G.5
Ferraro, M.B.6
Zanasi, R.7
Lazzeretti, P.8
-
27
-
-
33645276093
-
-
See also ref. [1]
-
e) See also ref. [1].
-
-
-
-
28
-
-
11244282931
-
-
Gaussian, Inc., Wallingford CT
-
Gaussian 03, Revision B.05 and C.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma. G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford CT, 2004.
-
(2004)
Gaussian 03, Revision B.05 and C.02
-
-
Frisch, M.J.1
Trucks, G.W.2
Schlegel, H.B.3
Scuseria, G.E.4
Robb, M.A.5
Cheeseman, J.R.6
Montgomery Jr., J.A.7
Vreven, T.8
Kudin, K.N.9
Burant, J.C.10
Millam, J.M.11
Iyengar, S.S.12
Tomasi, J.13
Barone, V.14
Mennucci, B.15
Cossi, M.16
Scalmani, G.17
Rega, N.18
Petersson, G.A.19
Nakatsuji, H.20
Hada, M.21
Ehara, M.22
Toyota, K.23
Fukuda, R.24
Hasegawa, J.25
Ishida, M.26
Nakajima, T.27
Honda, Y.28
Kitao, O.29
Nakai, H.30
Klene, M.31
Li, X.32
Knox, J.E.33
Hratchian, H.P.34
Cross, J.B.35
Bakken, V.36
Adamo, C.37
Jaramillo, J.38
Gomperts, R.39
Stratmann, R.E.40
Yazyev, O.41
Austin, A.J.42
Cammi, R.43
Pomelli, C.44
Ochterski, J.W.45
Ayala, P.Y.46
Morokuma, K.47
Voth, G.A.48
Salvador, P.49
Dannenberg, J.J.50
Zakrzewski, V.G.51
Dapprich, S.52
Daniels, A.D.53
Strain, M.C.54
Farkas, O.55
Malick, D.K.56
Rabuck, A.D.57
Raghavachari, K.58
Foresman, J.B.59
Ortiz, J.V.60
Cui, Q.61
Baboul, A.G.62
Clifford, S.63
Cioslowski, J.64
Stefanov, B.B.65
Liu, G.66
Liashenko, A.67
Piskorz, P.68
Komaromi, I.69
Martin, R.L.70
Fox, D.J.71
Keith, T.72
Al-Laham, M.A.73
Peng, C.Y.74
Nanayakkara, A.75
Challacombe, M.76
Gill, P.M.W.77
Johnson, B.78
Chen, W.79
Wong, M.W.80
Gonzalez, C.81
Pople, J.A.82
more..
-
29
-
-
33645318518
-
-
note
-
imag = 0).
-
-
-
-
30
-
-
84857628114
-
-
Gauge-independent atomic orbital, see; a) J. L. Dodds, R. McWeeny, A. J. Sadlej, Mol. Phys. 1980 41, 1419;
-
(1980)
Mol. Phys.
, vol.41
, pp. 1419
-
-
Dodds, J.L.1
McWeeny, R.2
Sadlej, A.J.3
-
31
-
-
11744305193
-
-
and references therein
-
b) K. Wolinski. J. F. Hilton, P. Pulay, J. Am. Chem. Soc. 1990, 112, 8251, and references therein.
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 8251
-
-
Wolinski, K.1
Hilton, J.F.2
Pulay, P.3
-
32
-
-
33645300446
-
-
note
-
[9] that could be studied within the same theoretical level.
-
-
-
-
33
-
-
0001041576
-
-
V. Gogonea, P. von R. Schleyer, P. R. Schreiner, Angew. Chem. 1998, 110, 2045;
-
(1998)
Angew. Chem.
, vol.110
, pp. 2045
-
-
Gogonea, V.1
Von Schleyer, P.R.2
Schreiner, P.R.3
-
35
-
-
33645284274
-
-
See, for example: a ref. [2]
-
See, for example: a) ref. [2].
-
-
-
-
36
-
-
33645305221
-
-
For statements concerning NICS(1) as a measure of aromaticity and antiaromaticity see, for example, ref. [4a]
-
b) For statements concerning NICS(1) as a measure of aromaticity and antiaromaticity see, for example, ref. [4a].
-
-
-
-
37
-
-
33645302447
-
-
note
-
The NICS scan of 4 is not indicative because the bq probe feels the effect of the hydrogen atoms of the trimethylsilyl groups. A similar effect (which, however, is remote enough and thus does not interfere with the shape close to the minima) can be observed in 3.
-
-
-
-
39
-
-
27744463786
-
-
b) D. Geuenich, K. Hess, F. Koehler, R. Herges, Chem. Rev. 2005, 105, 3758.
-
(2005)
Chem. Rev.
, vol.105
, pp. 3758
-
-
Geuenich, D.1
Hess, K.2
Koehler, F.3
Herges, R.4
-
40
-
-
5444255149
-
-
a) L. D. Shirtcliff, T. J. R. Weakley. M. M. Haley, F. Köhler, R. Herges, J. Org. Chem. 2004, 69, 6979;
-
(2004)
J. Org. Chem.
, vol.69
, pp. 6979
-
-
Shirtcliff, L.D.1
Weakley, T.J.R.2
Haley, M.M.3
Köhler, F.4
Herges, R.5
-
41
-
-
0037073157
-
-
b) D. B. Kimball, T. J. R. Weakley, R. Herges, M. M. Haley, J. Am. Chem. Soc. 2002, 124, 13463;
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 13463
-
-
Kimball, D.B.1
Weakley, T.J.R.2
Herges, R.3
Haley, M.M.4
-
42
-
-
18544396052
-
-
c) J. Rodriguez-Otero, E. M. Cabaleiro-Lago, J. M. Hermida-Ramon, A. Pena-Gallego, J. Org. Chem. 2003, 68, 8823.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 8823
-
-
Rodriguez-Otero, J.1
Cabaleiro-Lago, E.M.2
Hermida-Ramon, J.M.3
Pena-Gallego, A.4
-
43
-
-
33645327766
-
-
note
-
Please note that there are strong currents induced in the lone pairs of fluorine which, however, are isotropic.
-
-
-
|