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0012580121
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note
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In analogy to the larger and fully conjugated nanotubes, and for simplicity.
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0001419644
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0012621052
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Despite torsion of the double bonds in the neutral compound, the electronic structure is mainly quìnoìd, rather than benzoid, and is slightly antiaromatic with 16 π electrons in the periphery. This is confirmed by the ACID method: R. Herges, A. Papafilippopoulos, Angew. Chem. 2001, 113, 4809; Angew. Chem. Int. Ed. 2001, 40, 4671; R. Herges, D. Geuenich, J. Phys. Chem. A 2001, 105, 3214.
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0035905530
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Despite torsion of the double bonds in the neutral compound, the electronic structure is mainly quìnoìd, rather than benzoid, and is slightly antiaromatic with 16 π electrons in the periphery. This is confirmed by the ACID method: R. Herges, A. Papafilippopoulos, Angew. Chem. 2001, 113, 4809; Angew. Chem. Int. Ed. 2001, 40, 4671; R. Herges, D. Geuenich, J. Phys. Chem. A 2001, 105, 3214.
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13
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0035810502
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Despite torsion of the double bonds in the neutral compound, the electronic structure is mainly quìnoìd, rather than benzoid, and is slightly antiaromatic with 16 π electrons in the periphery. This is confirmed by the ACID method: R. Herges, A. Papafilippopoulos, Angew. Chem. 2001, 113, 4809; Angew. Chem. Int. Ed. 2001, 40, 4671; R. Herges, D. Geuenich, J. Phys. Chem. A 2001, 105, 3214.
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Herges, R.1
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14
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0012588780
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note
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min = 5 Hz, in the neutral state.
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15
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0012581093
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note
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1H NMR spectroscopy detected the formation of the anions.
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16
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0004171599
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VCH-Wiley, Weinheim
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π. In our case, ∑Δδ = 524 ppm. For a review, see: a) S. Braun, H.-O. Kalinowski, S. Berger, 150 and More Basic NMR Experiments: A Practical Course, VCH-Wiley, Weinheim, 1998;
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150 and More Basic NMR Experiments: A Practical Course
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Braun, S.1
Kalinowski, H.-O.2
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21
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0000368996
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a) A. Ayalon, M. Rabinovitz, P.-C. Cheng, L. T. Scott, Angew. Chem. 1992, 104, 1691; Angew. Chem. Int. Ed. Engl. 1992, 31, 1636;
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Ayalon, A.1
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a) A. Ayalon, M. Rabinovitz, P.-C. Cheng, L. T. Scott, Angew. Chem. 1992, 104, 1691; Angew. Chem. Int. Ed. Engl. 1992, 31, 1636;
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24
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0012531746
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note
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All structures were optimized at the B3LYP/6-31G* level of DFT theory within the corresponding point group, and confirmed by harmonic frequency analysis to be either minima or transition states. NMR shifts were calculated using the GIAO method. An extensive investigation of the energy hypersurface using the semiempirical PM3 method preceded the DFT calculations.
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25
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0012616523
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note
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Using standard 2D NMR techniques, that is, COSY, NOESY, HSQCSI, and HMBC.
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26
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0012590434
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note
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Clear nOe signals pertaining to carbon pairs 4 and 5, as well as 1 and 8, dismissed the possibility that the alternation is in a neutral-negative-neutral-negative fashion. A structure of two neutral anthracene units alternating with two anthracene dianion units is also possible, which gives the same symmetry. However, DFT calculations confirm the proposed structure, rather than this possibility.
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27
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0012588783
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note
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Quotation marks indicate that the dynamic process still exists in the tetraanion, although it is too slow to observe.
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28
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0004065524
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Academic Press, London
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1), from NOESY spectrum at 325 K (maximum working temperature for THF). See, for example: J. Sandström, Dynamic NMR Spectroscopy, Academic Press, London, 1982, p. 96.
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0012621055
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a) A. J. Kos, E. D. Jemmis, P. von R. Schleyer, R. Gleiter, U. Fischbach, J. A. Pople, J. Am. Chem. Soc. 1981, 103, 4996; For further olefinic and aromatic lithium complexes, see for example:
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Kos, A.J.1
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0000905085
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0033523605
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0012533333
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(Eds.: W. J. Hehre, L. Radom, P. von R. Schleyer, J. A. Pople), Wiley-Interscience, New York
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Ab Initio Molecular Orbital Theory, (Eds.: W. J. Hehre, L. Radom, P. von R. Schleyer, J. A. Pople), Wiley-Interscience, New York, 1986, p. 450.
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Ab Initio Molecular Orbital Theory
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39
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0012581094
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note
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In reference to the original double bonds in the neutral compound.
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40
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0012612127
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note
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2 carbon atoms of as much as 45.6 ppm.
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41
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0012612128
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note
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2 symmetry would give rise to 16 proton and 28 carbon resonances.
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42
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0003831080
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Wiley, New York
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M. Szwarc, Carbanions, living polymers, and electron transfer processes, Wiley, New York, 1968.
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Szwarc, M.1
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0028100743
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+ cations appear is reported in: A. Ayalon, A. Sygula, P.-C. Cheng, M. Rabinovitz, P. W. Rabideau, L. T. Scott, Science 1994, 265, 1065.
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Ayalon, A.1
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Rabinovitz, M.4
Rabideau, P.W.5
Scott, L.T.6
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44
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0012580126
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note
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+ complex.
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