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(b) Klevens, H. B.; Platt, J. R. J. Chem. Phys. 1949, 17, 470. Platt, J. R. Ann. Rev. Phys. Chem. 1959, 10, 354. The band designations given herein are those of Clar. Platt has proposed a different and more systematic naming system.
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8
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85033130490
-
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[n]Phenacenes with n up to 11 have been prepared (ref 4) and are remarkably stable
-
[n]Phenacenes with n up to 11 have been prepared (ref 4) and are remarkably stable.
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10
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Peck, R. C.; Schulman, J. M.; Disch, R. L. J. Phys. Chem. 1990, 94, 6637.
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Cioslowski, J.; Liu, G.; Martinov, M.; Piskorz, P.; Moncrieff, D. J. Am. Chem. Soc. 1996, 118, 5261. They state that the calculations were carried out at the B3LYP/6-311G** level, but the energies reported suggest that B3LYP/6-311G* was used.
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14
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33947299900
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Cf. Dewar, M. J. S.; de Llano, C. J. Am. Chem. Soc. 1969, 91, 789. Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1971, 93, 305, 2413. Herndon, W. C. J. Am. Chem. Soc. 1973, 95, 2404. Herndon, W. C.; Ellzey, M. L. J. Am. Chem. Soc. 1974, 96, 6631. Aihara, J. J. Am. Chem. Soc. 1976, 98, 2750; 1977, 99, 2048. Chestnut, D. B.; Davis, K. M. J. Comput. Chem. 1997, 18, 584.
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Cf. Dewar, M. J. S.; de Llano, C. J. Am. Chem. Soc. 1969, 91, 789. Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1971, 93, 305, 2413. Herndon, W. C. J. Am. Chem. Soc. 1973, 95, 2404. Herndon, W. C.; Ellzey, M. L. J. Am. Chem. Soc. 1974, 96, 6631. Aihara, J. J. Am. Chem. Soc. 1976, 98, 2750; 1977, 99, 2048. Chestnut, D. B.; Davis, K. M. J. Comput. Chem. 1997, 18, 584.
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16
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Cf. Dewar, M. J. S.; de Llano, C. J. Am. Chem. Soc. 1969, 91, 789. Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1971, 93, 305, 2413. Herndon, W. C. J. Am. Chem. Soc. 1973, 95, 2404. Herndon, W. C.; Ellzey, M. L. J. Am. Chem. Soc. 1974, 96, 6631. Aihara, J. J. Am. Chem. Soc. 1976, 98, 2750; 1977, 99, 2048. Chestnut, D. B.; Davis, K. M. J. Comput. Chem. 1997, 18, 584.
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Cf. Dewar, M. J. S.; de Llano, C. J. Am. Chem. Soc. 1969, 91, 789. Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1971, 93, 305, 2413. Herndon, W. C. J. Am. Chem. Soc. 1973, 95, 2404. Herndon, W. C.; Ellzey, M. L. J. Am. Chem. Soc. 1974, 96, 6631. Aihara, J. J. Am. Chem. Soc. 1976, 98, 2750; 1977, 99, 2048. Chestnut, D. B.; Davis, K. M. J. Comput. Chem. 1997, 18, 584.
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20
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Cf. Minkin, V. I.; Glukhovtsev, M. N.; Simkin, B. Y. Aromaticity and Antiaromaticity; Wiley: New York, 1994; pp 36-37. They recommend the HSE method which gives a resonance energy for naphthalene of 57 kcal/mol if benzene is taken as 36 kcal/mol. The HRE method would lead to a somewhat larger value of 66 kcal/mol. Wheland [Wheland, G. W. Resonance in Organic Chemistry, Wiley: New York, 1955] derived a resonance energy for naphthalene of 61 kcal/mol from thermochemical data. A value of 60 appears to be a reasonable average.
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0004238394
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Cf. Minkin, V. I.; Glukhovtsev, M. N.; Simkin, B. Y. Aromaticity and Antiaromaticity; Wiley: New York, 1994; pp 36-37. They recommend the HSE method which gives a resonance energy for naphthalene of 57 kcal/mol if benzene is taken as 36 kcal/mol. The HRE method would lead to a somewhat larger value of 66 kcal/mol. Wheland [Wheland, G. W. Resonance in Organic Chemistry, Wiley: New York, 1955] derived a resonance energy for naphthalene of 61 kcal/mol from thermochemical data. A value of 60 appears to be a reasonable average.
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(1955)
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Wheland, G.W.1
-
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-
-
85033157600
-
-
note
-
This is equivalent to using -38.708 53 per CH and -38.110 54 per C in defining the unstabilized counterparts. It represents a simple scaling scheme for extrapolating the thermochemical delocalization energies starting with those for benzene and naphthalene.
-
-
-
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25
-
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33751499022
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Cf. Goodman, L. , Ozkabak, A. G.; Thakur, S. N. J. Phys. Chem. 1991, 95, 9044.
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26
-
-
85033153040
-
-
note
-
2-hybridized carbons are 1.33 and 1.50 Å, respectively, for a difference of 0.17 Å.
-
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-
-
27
-
-
0002348678
-
-
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