메뉴 건너뛰기




Volumn 36, Issue 24, 1997, Pages 2761-2764

Theoretical Studies of the Structure, Aromaticity, and Magnetic Properties of o-Benzyne

Author keywords

1,2 didehydrobenzene; Aromaticity; Density functional calculations; NMR spectroscopy; Strained molecules

Indexed keywords


EID: 33750314789     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199727611     Document Type: Article
Times cited : (92)

References (70)
  • 8
    • 0000666476 scopus 로고
    • UV spectrum: J. G. G. Simon, N. Münzel, A. Schweig, Chem. Phys. Lett. 1990, 170, 187-192; microwave spectrum: R. D. Brown, P. D. Godfrey, M. J. Rodler, J. Am. Chem. Soc. 1986, 108, 1296-1297.
    • (1990) Chem. Phys. Lett. , vol.170 , pp. 187-192
    • Simon, J.G.G.1    Münzel, N.2    Schweig, A.3
  • 9
    • 33845375996 scopus 로고
    • UV spectrum: J. G. G. Simon, N. Münzel, A. Schweig, Chem. Phys. Lett. 1990, 170, 187-192; microwave spectrum: R. D. Brown, P. D. Godfrey, M. J. Rodler, J. Am. Chem. Soc. 1986, 108, 1296-1297.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 1296-1297
    • Brown, R.D.1    Godfrey, P.D.2    Rodler, M.J.3
  • 10
    • 33845279034 scopus 로고
    • IR spectrum: a) C. Wentrup, R. Blanch, H. Briel, G. Gross, J. Am. Chem. Soc. 1988, 110, 1874-1880; b) O. L. Chapman, C. C. Chang, J. Kolc, N. R. Rosenquist, H. Tomioka, ibid. 1975, 97, 6586-6588; c) O. L. Chapman, K. Mattes, C. L. McIntosh, J. Pacansky, G. V. Calder, G. Orr, ibid. 1973, 95, 6134-6135; d) J. G. Radziszewski, B. A. Hess, Jr., R. Zahradnik, ibid. 1992, 114, 52-51.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 1874-1880
    • Wentrup, C.1    Blanch, R.2    Briel, H.3    Gross, G.4
  • 11
    • 0000137480 scopus 로고
    • IR spectrum: a) C. Wentrup, R. Blanch, H. Briel, G. Gross, J. Am. Chem. Soc. 1988, 110, 1874-1880; b) O. L. Chapman, C. C. Chang, J. Kolc, N. R. Rosenquist, H. Tomioka, ibid. 1975, 97, 6586-6588; c) O. L. Chapman, K. Mattes, C. L. McIntosh, J. Pacansky, G. V. Calder, G. Orr, ibid. 1973, 95, 6134-6135; d) J. G. Radziszewski, B. A. Hess, Jr., R. Zahradnik, ibid. 1992, 114, 52-51.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 6586-6588
    • Chapman, O.L.1    Chang, C.C.2    Kolc, J.3    Rosenquist, N.R.4    Tomioka, H.5
  • 12
    • 0000856466 scopus 로고
    • IR spectrum: a) C. Wentrup, R. Blanch, H. Briel, G. Gross, J. Am. Chem. Soc. 1988, 110, 1874-1880; b) O. L. Chapman, C. C. Chang, J. Kolc, N. R. Rosenquist, H. Tomioka, ibid. 1975, 97, 6586-6588; c) O. L. Chapman, K. Mattes, C. L. McIntosh, J. Pacansky, G. V. Calder, G. Orr, ibid. 1973, 95, 6134-6135; d) J. G. Radziszewski, B. A. Hess, Jr., R. Zahradnik, ibid. 1992, 114, 52-51.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 6134-6135
    • Chapman, O.L.1    Mattes, K.2    McIntosh, C.L.3    Pacansky, J.4    Calder, G.V.5    Orr, G.6
  • 13
    • 0001815234 scopus 로고
    • IR spectrum: a) C. Wentrup, R. Blanch, H. Briel, G. Gross, J. Am. Chem. Soc. 1988, 110, 1874-1880; b) O. L. Chapman, C. C. Chang, J. Kolc, N. R. Rosenquist, H. Tomioka, ibid. 1975, 97, 6586-6588; c) O. L. Chapman, K. Mattes, C. L. McIntosh, J. Pacansky, G. V. Calder, G. Orr, ibid. 1973, 95, 6134-6135; d) J. G. Radziszewski, B. A. Hess, Jr., R. Zahradnik, ibid. 1992, 114, 52-51.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 52-151
    • Radziszewski, J.G.1    Hess Jr., B.A.2    Zahradnik, R.3
  • 30
    • 0000304399 scopus 로고
    • o) E. Kraka, D. Cremer, Chem. Phys. Lett. 1993, 216, 333-340; we thank Prof. Dr. D. Cremer for providing the CCSD(T)/6-31G** o-benzyne geometry;
    • (1993) Chem. Phys. Lett. , vol.216 , pp. 333-340
    • Kraka, E.1    Cremer, D.2
  • 32
    • 0030590163 scopus 로고    scopus 로고
    • q) R. Lindh, M. Schütz, Chem. Phys. Lett. 1996, 258, 409-415; the experimental and theoretical thermochemical data are summarized in this paper: see also ref. [3b,d].
    • (1996) Chem. Phys. Lett. , vol.258 , pp. 409-415
    • Lindh, R.1    Schütz, M.2
  • 36
    • 0000661478 scopus 로고    scopus 로고
    • R. Warmuth, Angew. Chem. 1997, 109, 1406-1409; Angew. Chem. Int. Ed. Engl. 1997, 36, 1347-1350.
    • (1997) Angew. Chem. , vol.109 , pp. 1406-1409
    • Warmuth, R.1
  • 37
    • 0030803420 scopus 로고    scopus 로고
    • R. Warmuth, Angew. Chem. 1997, 109, 1406-1409; Angew. Chem. Int. Ed. Engl. 1997, 36, 1347-1350.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 1347-1350
  • 49
    • 0001450708 scopus 로고    scopus 로고
    • b) H. Jiao, P. von R. Schleyer, Angew. Chem. 1996, 108, 2548-2551; Angew. Chem. Int. Ed. Engl. 1996, 35, 2383-2386;
    • (1996) Angew. Chem. , vol.108 , pp. 2548-2551
    • Jiao, H.1    Schleyer, P.V.R.2
  • 50
    • 0030445094 scopus 로고    scopus 로고
    • b) H. Jiao, P. von R. Schleyer, Angew. Chem. 1996, 108, 2548-2551; Angew. Chem. Int. Ed. Engl. 1996, 35, 2383-2386;
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 2383-2386
  • 52
    • 0030457576 scopus 로고    scopus 로고
    • c) G. Subramanian, P. von R. Schleyer, H. Jiao, ibid. 1996, 108, 2824-2827 and 1996, 35, 2638-2641;
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 2638-2641
  • 59
    • 0000814728 scopus 로고
    • For the calculation of chemical shifts, see V. G. Malkin, O. L. Malkina, M. E. Casida, D. R. Salahub, J. Am. Chem. Soc. 1994, 116, 5898-5908; for the calculation of coupling constants, see V. G. Malkin, O. L. Malkina, D. R. Salahub, Chem. Phys. Lett. 1994, 221, 91-99.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 5898-5908
    • Malkin, V.G.1    Malkina, O.L.2    Casida, M.E.3    Salahub, D.R.4
  • 60
    • 43949161745 scopus 로고
    • For the calculation of chemical shifts, see V. G. Malkin, O. L. Malkina, M. E. Casida, D. R. Salahub, J. Am. Chem. Soc. 1994, 116, 5898-5908; for the calculation of coupling constants, see V. G. Malkin, O. L. Malkina, D. R. Salahub, Chem. Phys. Lett. 1994, 221, 91-99.
    • (1994) Chem. Phys. Lett. , vol.221 , pp. 91-99
    • Malkin, V.G.1    Malkina, O.L.2    Salahub, D.R.3
  • 63
    • 33748247829 scopus 로고
    • a) P. von R. Schleyer, P. K. Freeman, H. Jiao, B. Goldfuß, Angew. Chem. 1995, 107, 332-335; Angew. Chem. Int. Ed. Engl. 1995, 34, 337-340;
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 337-340
  • 68
    • 0642285104 scopus 로고    scopus 로고
    • note
    • -1 based on the homodesmotic equation: 3 × (transbutadiene - ethylene) = benzene (see ref. [22c]).
  • 69
    • 0642346444 scopus 로고    scopus 로고
    • note
    • x (Becke3LYP/6-311 + G**).
  • 70
    • 0003780688 scopus 로고
    • Chapman and Hall, London
    • -1 for trans-butadiene; see J. B. Pedley, R. D. Naylor, S. P. Kirby, Thermochemical Data of Organic Compounds, 2nd ed., Chapman and Hall, London, 1986. The Becke3LYP/6-311 + G** total energies including thermal correction at 298 K are -230.89237 for 1, -157.16078 for trans-2-butene, - 232.20578 for benzene, and -155.95047 for trans-butadiene.
    • (1986) Thermochemical Data of Organic Compounds, 2nd Ed.
    • Pedley, J.B.1    Naylor, R.D.2    Kirby, S.P.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.