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CRC Press: Boca Raton, Chapter 4
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(b) Balaban, A. T.; Banciu, M.; Ciorba, V. Annulenes, Benzo-, Hetero-, Homo-Derivatives, and their Valence Isomers; CRC Press: Boca Raton, 1987; Vol. I, Chapter 4.
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Masamune, S.1
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(d) Hernando, J. M.; Enríquez, F.; Quirante, J. J. J. Mol. Struct. (THEOCHEM) 1993, 287, 131.
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(d) Sulzbach, H. M.; Schaefer, H. F.; Klopper, W.; Lüthi, H. P. J. Am. Chem. Soc. 1996, 118, 3519.
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0033601062
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(e) King, R. A.; Crawford, T. D.; Stanton, J. F.; Schaefer, H. F. J. Am. Chem. Soc. 1999, 121, 10788.
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4644338165
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Wannere, C. S.; Sattelmeyer, K. W.; Schaefer, H. F.; Schleyer, P. v. R. Angew. Chem. Int. Ed. 2004, 43, 4200.
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20
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33645772575
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note
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5e This suggests that CCSD(T)//B3LYP relative energies for 3 and 5 would also be comparable to CCSD(T)//CCSD(T) relative energies.
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21
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33645792021
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note
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5e), it nevertheless does reasonably well at estimating the degree of delocalization in these systems (e.g., as manifested in Δr). For this reason, BH&HLYP is more reliable than B3LYP when the geometries obtained are to be evaluated for magnetic properties and aromaticity.
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23
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0038596731
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(b) Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200.
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Miehlich, B.1
Savin, A.2
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Preuss, H.4
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26
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0006244148
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(b) Raghavachari, K.; Trucks, G. W.; Pople, J. A.; Head-Gordon, M. Chem. Phys. Lett. 1989, 157, 479.
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Chem. Phys. Lett.
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Trucks, G.W.2
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29
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33947315480
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Dauben, H. J.; Wilson, J. D.; Laity, J. L. J. Am. Chem. Soc. 1968, 90, 811.
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Dauben, H.J.1
Wilson, J.D.2
Laity, J.L.3
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30
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33645758130
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note
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17b was complicated in the very nonplanar species, primarily because of local effects involving nearby π bonds, and in other species (e.g., 2, 4, and 5) because of extreme proximity of the inner hydrogen nuclei to the ring centroid. These effects rendered this method less attractive than MSE.
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31
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0011190497
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(b) Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. J. R. v. E. J. Am. Chem. Soc. 1996, 118, 6317.
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Schleyer, P.V.R.1
Maerker, C.2
Dransfeld, A.3
Jiao, H.4
Hommes, N.J.R.V.E.5
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34
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0345491105
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(b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
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Phys. Rev. B
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Lee, C.1
Yang, W.2
Parr, R.G.3
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40
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22144476163
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Castro, C.; Karney, W. L.; Valencia, M. A.; Vu, C. M. H.; Pemberton, R. P. J. Am. Chem. Soc. 2005, 127, 9704.
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Castro, C.1
Karney, W.L.2
Valencia, M.A.3
Vu, C.M.H.4
Pemberton, R.P.5
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41
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12044257767
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See, for example, the comparison of ring inversion and nonplanar bond shifting in cyclooctatetraene: Paquette, L. A. Acc. Chem. Res. 1993, 26, 57.
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Acc. Chem. Res.
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Paquette, L.A.1
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42
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27144509804
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For a recent example of two-twist topology in [14]annulene, see: Rzepa, H. Org. Lett. 2005, 7, 4637.
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Org. Lett.
, vol.7
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Rzepa, H.1
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43
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0035938229
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Scott, L. T.; Sumpter, C. A.; Gantzel, P. K.; Maverick, E.; Trueblood, K. N. Tetrahedron 2001, 57, 3795.
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Tetrahedron
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Scott, L.T.1
Sumpter, C.A.2
Gantzel, P.K.3
Maverick, E.4
Trueblood, K.N.5
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44
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33645757426
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note
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NICS computed at the CSGT-B3LYP/6-311+G**//BH&HLYP/6- 311+G** level.
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45
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33645793648
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note
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-1).
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46
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33645778909
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note
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3b
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47
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33645754361
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note
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For a detailed discussion of this type of analysis on other annulenes, see ref 23.
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48
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33645780299
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note
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See also ref 24 for other highly aromatic bond-shifting transition states with large torsion angles.
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