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Volumn , Issue 34, 2007, Pages 5717-5725

A simple and intuitive description of C-H bond energies

Author keywords

C H bond dissociation energies; DFT calculations; Hybridization; NBO analysis

Indexed keywords


EID: 36848998796     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700419     Document Type: Article
Times cited : (10)

References (23)
  • 14
    • 36849037245 scopus 로고    scopus 로고
    • Gaussian 03, Revision B.05, 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, M. 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. N
    • Gaussian 03, Revision B.05, 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, M. 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. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc.; Wallingford CT, 2004.
  • 15
    • 0011083499 scopus 로고    scopus 로고
    • Gaussian NBO (Natural Bond Orbitals) Version 3.1 was used. See A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899 and references cited therein
    • Gaussian NBO (Natural Bond Orbitals) Version 3.1 was used. See A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899 and references cited therein.
  • 17
    • 36849014655 scopus 로고    scopus 로고
    • NBO charges, although different from Mulliken charges show the same trend. Thus, for the optimized propene, the 75 and 90 degrees bent propenes the charges of the CH2, CH and CH3 moieties are: -0.01797, 0.01238, 0.0056; -0.004535, 0.05528, 0.00992; -0.00065, 0.1559, 0.15656
    • 3 moieties are: -0.01797, +0.01238, +0.0056; -0.004535, +0.05528, -0.00992; -0.00065, -0.1559, +0.15656.
  • 18
    • 34250893847 scopus 로고    scopus 로고
    • Fluorine-containing compounds have been shown to be problematic for calculations (see, for example, H. Wei, D. A. Hrovat, W. R. Dolbier, B. E. Smart Jr, W. T. Borden, Angew. Chem. Int. Ed. 2007, 46, 2666 and references cited therein). Therefore, if fluorine containing compounds are well handled within a given approach it proves this approach to be more general.
    • Fluorine-containing compounds have been shown to be problematic for calculations (see, for example, H. Wei, D. A. Hrovat, W. R. Dolbier, B. E. Smart Jr, W. T. Borden, Angew. Chem. Int. Ed. 2007, 46, 2666 and references cited therein). Therefore, if fluorine containing compounds are well handled within a given approach it proves this approach to be more general.
  • 19
    • 32144434172 scopus 로고    scopus 로고
    • Usually NICS is used in conjugated cyclic systems. However, NICS scan (A. Stanger, J. Org. Chem. 2006, 71, 883) that measures ring currents can be used for observing these differences.
    • Usually NICS is used in conjugated cyclic systems. However, NICS scan (A. Stanger, J. Org. Chem. 2006, 71, 883) that measures ring currents can be used for observing these differences.
  • 20
    • 36849047652 scopus 로고    scopus 로고
    • Reported are the average values ± σ
    • Reported are the average values ± σ.
  • 21
    • 36849029665 scopus 로고    scopus 로고
    • CPU time on a PC with Windows XP™ as operating system, using the Windows version of G03 and a starting geometry of Gauss View was 76 and 24 seconds for 36 and 37, respectively, for geometry optimization and NBO analysis.
    • CPU time on a PC with Windows XP™ as operating system, using the Windows version of G03 and a starting geometry of Gauss View was 76 and 24 seconds for 36 and 37, respectively, for geometry optimization and NBO analysis.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.