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Volumn 62, Issue 17, 1997, Pages 5720-5727

Properties of Some Condensed Aromatic Systems

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EID: 0000540373     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961831j     Document Type: Article
Times cited : (141)

References (59)
  • 3
    • 36849137462 scopus 로고
    • (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.
    • (1949) J. Chem. Phys. , vol.17 , pp. 470
    • Klevens, H.B.1    Platt, J.R.2
  • 4
    • 36849137462 scopus 로고
    • (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.
    • (1959) Ann. Rev. Phys. Chem. , vol.10 , pp. 354
    • Platt, J.R.1
  • 5
    • 67949099684 scopus 로고
    • Clar, E. Chem Ber. 1939, 72, 1817.
    • (1939) Chem Ber. , vol.72 , pp. 1817
    • Clar, E.1
  • 7
  • 8
    • 85033130490 scopus 로고    scopus 로고
    • [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.
  • 14
    • 33947299900 scopus 로고
    • 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.
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 789
    • Dewar, M.J.S.1    De Llano, C.2
  • 15
    • 33947293579 scopus 로고
    • 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.
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 305
    • Hess, B.A.1    Schaad, L.J.2
  • 16
    • 33947085335 scopus 로고
    • 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.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 2404
    • Herndon, W.C.1
  • 17
    • 33847803218 scopus 로고
    • 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.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 6631
    • Herndon, W.C.1    Ellzey, M.L.2
  • 18
    • 0000109325 scopus 로고
    • 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.
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 2750
    • Aihara, J.1
  • 19
    • 0011708818 scopus 로고
    • 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.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 2048
  • 20
    • 33748509713 scopus 로고    scopus 로고
    • 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.
    • (1997) J. Comput. Chem. , vol.18 , pp. 584
    • Chestnut, D.B.1    Davis, K.M.2
  • 21
    • 0004024319 scopus 로고
    • Wiley: New York
    • 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.
    • (1994) Aromaticity and Antiaromaticity , pp. 36-37
    • Minkin, V.I.1    Glukhovtsev, M.N.2    Simkin, B.Y.3
  • 22
    • 0004238394 scopus 로고
    • Wiley: New York
    • 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.
    • (1955) Resonance in Organic Chemistry
    • Wheland, G.W.1
  • 23
    • 85033157600 scopus 로고    scopus 로고
    • 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.
  • 26
    • 85033153040 scopus 로고    scopus 로고
    • note
    • 2-hybridized carbons are 1.33 and 1.50 Å, respectively, for a difference of 0.17 Å.
  • 27
    • 0002348678 scopus 로고
    • Berry, R. S. J. Chem. Phys. 1961, 35, 29. Shaik, S. S.; Bar, R. Nouv. J. Chim. 1984, 8, 411. Hiberty, P. C.; Shaik, S. S.; Lefour, J.-M.; Ohanessian, G. J. Org. Chem. 1985, 50, 4657. Shaik, S. S.; Hiberty, P. C.; Lefour, J.-M.; Ohanessian, G. J. Am. Chem. Soc. 1987, 109, 363. Shaik, S. S.; Hiberty, P. C.; Lefour, J.-M.; Ohanessian, G. J. Phys. Chem. 1988, 92, 5086. Hiberty, P. C. In Topics in Current Chemistry; Gutman, I., Cyrin, S. J., Eds., Springer: New York, 1990; Vol. 153, p 27. Jug, K.; Koster, A. M. J. Am. Chem. Soc. 1990, 112, 6772.
    • (1961) J. Chem. Phys. , vol.35 , pp. 29
    • Berry, R.S.1
  • 28
    • 0000695013 scopus 로고
    • Berry, R. S. J. Chem. Phys. 1961, 35, 29. Shaik, S. S.; Bar, R. Nouv. J. Chim. 1984, 8, 411. Hiberty, P. C.; Shaik, S. S.; Lefour, J.-M.; Ohanessian, G. J. Org. Chem. 1985, 50, 4657. Shaik, S. S.; Hiberty, P. C.; Lefour, J.-M.; Ohanessian, G. J. Am. Chem. Soc. 1987, 109, 363. Shaik, S. S.; Hiberty, P. C.; Lefour, J.-M.; Ohanessian, G. J. Phys. Chem. 1988, 92, 5086. Hiberty, P. C. In Topics in Current Chemistry; Gutman, I., Cyrin, S. J., Eds., Springer: New York, 1990; Vol. 153, p 27. Jug, K.; Koster, A. M. J. Am. Chem. Soc. 1990, 112, 6772.
    • (1984) Nouv. J. Chim. , vol.8 , pp. 411
    • Shaik, S.S.1    Bar, R.2
  • 29
    • 0011809412 scopus 로고
    • Berry, R. S. J. Chem. Phys. 1961, 35, 29. Shaik, S. S.; Bar, R. Nouv. J. Chim. 1984, 8, 411. Hiberty, P. C.; Shaik, S. S.; Lefour, J.-M.; Ohanessian, G. J. Org. Chem. 1985, 50, 4657. Shaik, S. S.; Hiberty, P. C.; Lefour, J.-M.; Ohanessian, G. J. Am. Chem. Soc. 1987, 109, 363. Shaik, S. S.; Hiberty, P. C.; Lefour, J.-M.; Ohanessian, G. J. Phys. Chem. 1988, 92, 5086. Hiberty, P. C. In Topics in Current Chemistry; Gutman, I., Cyrin, S. J., Eds., Springer: New York, 1990; Vol. 153, p 27. Jug, K.; Koster, A. M. J. Am. Chem. Soc. 1990, 112, 6772.
    • (1985) J. Org. Chem. , vol.50 , pp. 4657
    • Hiberty, P.C.1    Shaik, S.S.2    Lefour, J.-M.3    Ohanessian, G.4
  • 30
    • 33845283454 scopus 로고
    • Berry, R. S. J. Chem. Phys. 1961, 35, 29. Shaik, S. S.; Bar, R. Nouv. J. Chim. 1984, 8, 411. Hiberty, P. C.; Shaik, S. S.; Lefour, J.-M.; Ohanessian, G. J. Org. Chem. 1985, 50, 4657. Shaik, S. S.; Hiberty, P. C.; Lefour, J.-M.; Ohanessian, G. J. Am. Chem. Soc. 1987, 109, 363. Shaik, S. S.; Hiberty, P. C.; Lefour, J.-M.; Ohanessian, G. J. Phys. Chem. 1988, 92, 5086. Hiberty, P. C. In Topics in Current Chemistry; Gutman, I., Cyrin, S. J., Eds., Springer: New York, 1990; Vol. 153, p 27. Jug, K.; Koster, A. M. J. Am. Chem. Soc. 1990, 112, 6772.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 363
    • Shaik, S.S.1    Hiberty, P.C.2    Lefour, J.-M.3    Ohanessian, G.4
  • 31
    • 0000903479 scopus 로고
    • Berry, R. S. J. Chem. Phys. 1961, 35, 29. Shaik, S. S.; Bar, R. Nouv. J. Chim. 1984, 8, 411. Hiberty, P. C.; Shaik, S. S.; Lefour, J.-M.; Ohanessian, G. J. Org. Chem. 1985, 50, 4657. Shaik, S. S.; Hiberty, P. C.; Lefour, J.-M.; Ohanessian, G. J. Am. Chem. Soc. 1987, 109, 363. Shaik, S. S.; Hiberty, P. C.; Lefour, J.-M.; Ohanessian, G. J. Phys. Chem. 1988, 92, 5086. Hiberty, P. C. In Topics in Current Chemistry; Gutman, I., Cyrin, S. J., Eds., Springer: New York, 1990; Vol. 153, p 27. Jug, K.; Koster, A. M. J. Am. Chem. Soc. 1990, 112, 6772.
    • (1988) J. Phys. Chem. , vol.92 , pp. 5086
    • Shaik, S.S.1    Hiberty, P.C.2    Lefour, J.-M.3    Ohanessian, G.4
  • 32
    • 0001891134 scopus 로고
    • Gutman, I., Cyrin, S. J., Eds., Springer: New York
    • Berry, R. S. J. Chem. Phys. 1961, 35, 29. Shaik, S. S.; Bar, R. Nouv. J. Chim. 1984, 8, 411. Hiberty, P. C.; Shaik, S. S.; Lefour, J.-M.; Ohanessian, G. J. Org. Chem. 1985, 50, 4657. Shaik, S. S.; Hiberty, P. C.; Lefour, J.-M.; Ohanessian, G. J. Am. Chem. Soc. 1987, 109, 363. Shaik, S. S.; Hiberty, P. C.; Lefour, J.-M.; Ohanessian, G. J. Phys. Chem. 1988, 92, 5086. Hiberty, P. C. In Topics in Current Chemistry; Gutman, I., Cyrin, S. J., Eds., Springer: New York, 1990; Vol. 153, p 27. Jug, K.; Koster, A. M. J. Am. Chem. Soc. 1990, 112, 6772.
    • (1990) Topics in Current Chemistry , vol.153 , pp. 27
    • Hiberty, P.C.1
  • 33
    • 0000698646 scopus 로고
    • Berry, R. S. J. Chem. Phys. 1961, 35, 29. Shaik, S. S.; Bar, R. Nouv. J. Chim. 1984, 8, 411. Hiberty, P. C.; Shaik, S. S.; Lefour, J.-M.; Ohanessian, G. J. Org. Chem. 1985, 50, 4657. Shaik, S. S.; Hiberty, P. C.; Lefour, J.-M.; Ohanessian, G. J. Am. Chem. Soc. 1987, 109, 363. Shaik, S. S.; Hiberty, P. C.; Lefour, J.-M.; Ohanessian, G. J. Phys. Chem. 1988, 92, 5086. Hiberty, P. C. In Topics in Current Chemistry; Gutman, I., Cyrin, S. J., Eds., Springer: New York, 1990; Vol. 153, p 27. Jug, K.; Koster, A. M. J. Am. Chem. Soc. 1990, 112, 6772.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 6772
    • Jug, K.1    Koster, A.M.2
  • 38
    • 0001463441 scopus 로고
    • Fulton, R. L. J. Phys. Chem. 1993, 97, 7516. Fulton, R. L.; Mixon, S. T. J. Phys. Chem. 1993, 97, 7530.
    • (1993) J. Phys. Chem. , vol.97 , pp. 7516
    • Fulton, R.L.1
  • 42
    • 0040963619 scopus 로고
    • Clark, P. A.; Brogli, F.; Heilbronner, E. Helv. Chim. Acta 1972, 55, 1415. Biemann, D.; Schmidt, W. J. Am. Chem. Soc. 1980, 102, 3163.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 3163
    • Biemann, D.1    Schmidt, W.2
  • 45
    • 1542537472 scopus 로고
    • McClure, D. S. J. Chem. Phys. 1954, 22, 1256, 1668. Sidman, J. W. J. Chem. Phys. 1956, 25, 115, 122.
    • (1954) J. Chem. Phys. , vol.22 , pp. 1256
    • McClure, D.S.1
  • 46
    • 0037993739 scopus 로고
    • McClure, D. S. J. Chem. Phys. 1954, 22, 1256, 1668. Sidman, J. W. J. Chem. Phys. 1956, 25, 115, 122.
    • (1956) J. Chem. Phys. , vol.25 , pp. 115
    • Sidman, J.W.1
  • 48
    • 0343390578 scopus 로고
    • Pariser, R.; Parr, R. G. J. Chem. Phys. 1953, 21, 466, 767. Parr, R. G.; Pariser, R. J. Chem. Phys. 1955, 23, 711. Pariser, R. J. Chem. Phys. 1956, 25, 1112. Pople, J. A. Trans. Faraday Soc. 1953, 49, 1375; Proc. Phys. Soc. 1955, 68A, 81.
    • (1953) J. Chem. Phys. , vol.21 , pp. 466
    • Pariser, R.1    Parr, R.G.2
  • 49
    • 0042253626 scopus 로고
    • Pariser, R.; Parr, R. G. J. Chem. Phys. 1953, 21, 466, 767. Parr, R. G.; Pariser, R. J. Chem. Phys. 1955, 23, 711. Pariser, R. J. Chem. Phys. 1956, 25, 1112. Pople, J. A. Trans. Faraday Soc. 1953, 49, 1375; Proc. Phys. Soc. 1955, 68A, 81.
    • (1955) J. Chem. Phys. , vol.23 , pp. 711
    • Parr, R.G.1    Pariser, R.2
  • 50
    • 0007721510 scopus 로고
    • Pariser, R.; Parr, R. G. J. Chem. Phys. 1953, 21, 466, 767. Parr, R. G.; Pariser, R. J. Chem. Phys. 1955, 23, 711. Pariser, R. J. Chem. Phys. 1956, 25, 1112. Pople, J. A. Trans. Faraday Soc. 1953, 49, 1375; Proc. Phys. Soc. 1955, 68A, 81.
    • (1956) J. Chem. Phys. , vol.25 , pp. 1112
    • Pariser, R.1
  • 51
    • 34748873709 scopus 로고
    • Pariser, R.; Parr, R. G. J. Chem. Phys. 1953, 21, 466, 767. Parr, R. G.; Pariser, R. J. Chem. Phys. 1955, 23, 711. Pariser, R. J. Chem. Phys. 1956, 25, 1112. Pople, J. A. Trans. Faraday Soc. 1953, 49, 1375; Proc. Phys. Soc. 1955, 68A, 81.
    • (1953) Trans. Faraday Soc. , vol.49 , pp. 1375
    • Pople, J.A.1
  • 52
    • 0343390578 scopus 로고
    • Pariser, R.; Parr, R. G. J. Chem. Phys. 1953, 21, 466, 767. Parr, R. G.; Pariser, R. J. Chem. Phys. 1955, 23, 711. Pariser, R. J. Chem. Phys. 1956, 25, 1112. Pople, J. A. Trans. Faraday Soc. 1953, 49, 1375; Proc. Phys. Soc. 1955, 68A, 81.
    • (1955) Proc. Phys. Soc. , vol.68 A , pp. 81
  • 54
    • 0001074825 scopus 로고
    • Pauling, L.; Brockway, L. O.; Beach, J. Y. J. Am. Chem. Soc. 1935, 57, 2705. Pauling, L.; Brockway, L. O. J. Am. Chem. Soc. 1937, 59, 1223.
    • (1937) J. Am. Chem. Soc. , vol.59 , pp. 1223
    • Pauling, L.1    Brockway, L.O.2
  • 56
    • 85033142632 scopus 로고    scopus 로고
    • Yale University
    • Keith, T. A., Yale University. This is based on PROAIM: Biegler-König, F. W.; Bader, R. F. W.; Tang, T.-H. J. Comput. Chem. 1982, 3, 317.
    • Keith, T.A.1


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