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Volumn 36, Issue 12, 2007, Pages 1438-1439

Synthesis and structure of a carbon compound bearing a sterically rigid 1,8-dioxythioxanthylium (or thioxanthene) skeleton

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EID: 38149028330     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2007.1438     Document Type: Article
Times cited : (3)

References (20)
  • 6
    • 0004204702 scopus 로고    scopus 로고
    • 3rd ed, Oxford University Press
    • J. Emsley, The Elements, 3rd ed., Oxford University Press, 1998.
    • (1998) The Elements
    • Emsley, J.1
  • 12
    • 38149113318 scopus 로고    scopus 로고
    • When 1 equiv. of the oxidant was used, the reaction afforded the mixture of 6 and 7, which did not show the ESR signals. The results indicate this reaction proceeds by two-electron oxidation.
    • When 1 equiv. of the oxidant was used, the reaction afforded the mixture of 6 and 7, which did not show the ESR signals. The results indicate this reaction proceeds by two-electron oxidation.
  • 13
    • 38149080318 scopus 로고    scopus 로고
    • 3J = 8 Hz).
    • 3J = 8 Hz).
  • 14
    • 38149115144 scopus 로고    scopus 로고
    • Data for 4: Mp 198-199°C. 1HNMR (400 MHz, CDCl 3) δ 2.08 (s, 6H, 6.41 (d, 1H, 3J, 9Hz, 6.55 (d, 1H, 3J, 7 Hz, 6.71 (d, 1H, 3J, 8 Hz, 6.91 (d, 1H, 3J, 8 Hz, 7.20 (dd, 1H, 3J, 9Hz, 3J, 7 Hz, 7.51 (t, 1H, 3J, 8 Hz, 13CNMR (100MHz, CDCl3) δ 21.7 (CH3, 99.5 (C, 106.2 (CH, 110.5 (CH, 114.4 (CH, 120.1 (C, 120.5 (C, 124.4 (CH, 135.9 (C, 137.5 (CH, 137.6 (CH, 138.3 (C, 164.7 (C, 168.7 (C, 183.0 (C, UV-vis (CH2Cl2) λmax (log ε, 272 (4.22, 337 (4.14, 448 (3.88, 615 3.71
    • max (log ε): 272 (4.22), 337 (4.14), 448 (3.88), 615 (3.71).
  • 15
    • 38149076968 scopus 로고    scopus 로고
    • Crystal data for 4: C16H12O2S, fw 268.32, orthorhombic, Pbca (No. 61, a, 12.1950(3, b, 13.6590(4, c, 15.0020(3) Å, V, 2498.91(11) Å3, Z, 8, Dcalcd, 1.426 g/cm3, R, 0.0586 (I > 2σ(I, Rw, 0.1861 (all data, GOF =1.185 for 2972 reflections and 200 parameters. The data were collected at 173 K using a Mac Science DIP 2030 imaging plate equipped with graphite-monochromated Mo Kα radiation (λ, 0.71073Å, In the X-ray structure of 4, O1, O2, and C14 are disordered and the proportion of the major structure is 81, The structure of the remaining 19% is similar to the major one (01′-C14′, 2.96(3) Å, O2̊-C14′, 1.48(3) Å, CCDC-663067
    • w = 0.1861 (all data), GOF =1.185 for 2972 reflections and 200 parameters. The data were collected at 173 K using a Mac Science DIP 2030 imaging plate equipped with graphite-monochromated Mo Kα radiation (λ = 0.71073Å). In the X-ray structure of 4, O1, O2, and C14 are disordered and the proportion of the major structure is 81%. The structure of the remaining 19% is similar to the major one (01′-C14′ = 2.96(3) Å, O2̊-C14′ = 1.48(3) Å) (CCDC-663067).
  • 16
    • 38149090022 scopus 로고    scopus 로고
    • The structure was optimized by the density functional theory (DFT) at the B3PW91/6-31G(d) level14 using the Gaussian 98 program, out at the same level
    • 15The AIM analysis was carried out at the same level.
    • 15The AIM analysis was carried
  • 20
    • 38149050341 scopus 로고    scopus 로고
    • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, Jr, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniel, S. K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98, revision A.5; Gaussian, Inc, Pittsburgh, PA, 1998
    • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, Jr., J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniel, S. K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98, revision A.5; Gaussian, Inc.: Pittsburgh, PA, 1998.


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