메뉴 건너뛰기




Volumn , Issue 22, 2007, Pages 3491-3496

1,3-Dipolarophile character of an extremely bulky phosphaalkyne Mes*C≡P (Mes* = 2,4,6-tBu3C6H 2) leading to the formation of 1,2,4-diazaphospholes with unique hydrogen bonding properties

Author keywords

Cycloaddition; DFT calculations; Heterocycles; Hydrogen bonds; Phosphaalkynes; X ray crystallography

Indexed keywords

CRYSTAL STRUCTURE; SPECTROSCOPIC ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 34547805273     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200700180     Document Type: Article
Times cited : (6)

References (55)
  • 6
    • 85163244582 scopus 로고    scopus 로고
    • Recent reports on P-heterocycles prepared from t-BuC≡P: a F. G. N. Cloke, J. C. Green, N. Hazari, P. B. Hitchcock, P. Mountfold, J. F. Nixon, D. J. Wilson, Organometallics 2006, 25, 3688;
    • Recent reports on P-heterocycles prepared from t-BuC≡P: a) F. G. N. Cloke, J. C. Green, N. Hazari, P. B. Hitchcock, P. Mountfold, J. F. Nixon, D. J. Wilson, Organometallics 2006, 25, 3688;
  • 11
    • 85163247045 scopus 로고    scopus 로고
    • 2) is reported to react with dienes to give [2+4] adducts: A. Mack, E. Pierron, T. Allspach, U. Bergsträ≡er, M. Regitz, Synthesis 1998, 1305.
    • 2) is reported to react with dienes to give [2+4] adducts: A. Mack, E. Pierron, T. Allspach, U. Bergsträ≡er, M. Regitz, Synthesis 1998, 1305.
  • 30
    • 85163249403 scopus 로고    scopus 로고
    • Previous theoretical studies on diazaphospholes: L. Nyulászi, P. Várnai, W. Eisfeld, M. Regitz, J. Comput. Chem. 1997, 18, 609.
    • Previous theoretical studies on diazaphospholes: L. Nyulászi, P. Várnai, W. Eisfeld, M. Regitz, J. Comput. Chem. 1997, 18, 609.
  • 31
    • 85163248625 scopus 로고    scopus 로고
    • Previous theoretical studies on silyl migration: T. J. Barton, J. Lin, S. Ijadi-Maghsoodi, M. D. Power, X. Zhang, Z. Ma, H. Shimizu, M. S. Gordon, J. Am. Chem. Soc. 1995, 117, 11695.
    • Previous theoretical studies on silyl migration: T. J. Barton, J. Lin, S. Ijadi-Maghsoodi, M. D. Power, X. Zhang, Z. Ma, H. Shimizu, M. S. Gordon, J. Am. Chem. Soc. 1995, 117, 11695.
  • 32
    • 85163246554 scopus 로고    scopus 로고
    • 3- and H-migration, respectively [B3LYP/6-31+G(d) level]. The total energy of 3-silyl-1H-1,2, 4-diazaphosphole is close to that of 5-silyl-1H-1,2,4-diazaphosphole. See Supporting Information.
    • 3- and H-migration, respectively [B3LYP/6-31+G(d) level]. The total energy of 3-silyl-1H-1,2, 4-diazaphosphole is close to that of 5-silyl-1H-1,2,4-diazaphosphole. See Supporting Information.
  • 33
    • 85163244348 scopus 로고    scopus 로고
    • -1 at the B3LYP/6-31+G(d) level of calculation because of the steric repulsion between methyl and trimethylsilyl groups.
    • -1 at the B3LYP/6-31+G(d) level of calculation because of the steric repulsion between methyl and trimethylsilyl groups.
  • 34
    • 85163247496 scopus 로고    scopus 로고
    • -1 at the B3LYP/6-31+G(d) level. See Supporting Information.
    • -1 at the B3LYP/6-31+G(d) level. See Supporting Information.
  • 35
    • 85163247046 scopus 로고    scopus 로고
    • In the previous studies on symmetrically 3,5-disubstituted 1H-1,2,4-diazaphospholes, the C-3 position was assigned on the basis of the slightly smaller 1JPC constant: R. M. Claramunt, C. López, A. Schmidpeter, A. Willhalm, J. Elguero, I. Alkorta, Spectroscopy 2001, 15, 27
    • PC constant: R. M. Claramunt, C. López, A. Schmidpeter, A. Willhalm, J. Elguero, I. Alkorta, Spectroscopy 2001, 15, 27.
  • 37
    • 85163246580 scopus 로고    scopus 로고
    • Compound 10 was alternatively obtained from 1 and diazomethane in 79% yield: Y. Kawai, Dissertation, Tohoku University, 1990.
    • Compound 10 was alternatively obtained from 1 and diazomethane in 79% yield: Y. Kawai, Dissertation, Tohoku University, 1990.
  • 42
    • 85163246425 scopus 로고    scopus 로고
    • In the structures of pyrazoles, molecular aggregation for the sake of hydrogen bonds and C-H⋯π interactions has been observed: a A. Haghiri, H.-W. Lerner, M. Wagner, J. W. Bats, Acta Crystallogr, Sect. E 2002, 58, o1378;
    • In the structures of pyrazoles, molecular aggregation for the sake of hydrogen bonds and C-H⋯π interactions has been observed: a) A. Haghiri, H.-W. Lerner, M. Wagner, J. W. Bats, Acta Crystallogr., Sect. E 2002, 58, o1378;
  • 45
    • 85163248455 scopus 로고    scopus 로고
    • [21].
    • [21].
  • 49
    • 85163244089 scopus 로고    scopus 로고
    • Bond lengths of 1.33280 and 1.35033 Å were theoretically determined for the two C=N bonds of 9xx at the B3LYP/6-31+G(d) level.
    • Bond lengths of 1.33280 and 1.35033 Å were theoretically determined for the two C=N bonds of 9xx at the B3LYP/6-31+G(d) level.
  • 54
    • 85163244637 scopus 로고    scopus 로고
    • Crystal Structure Analysis Package, Molecular Structure Corporation, The Woodlands, TX, 1985 and 1999.
    • Crystal Structure Analysis Package, Molecular Structure Corporation, The Woodlands, TX, 1985 and 1999.
  • 55
    • 85163247796 scopus 로고    scopus 로고
    • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, N. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. M
    • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, N. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. M. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision D.01, Gaussian Inc., Wallingford CT, 2004.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.