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Volumn 118, Issue 34, 1996, Pages 8048-8055

Tautomerism, ionization, and bond dissociations of 5-nitro-2,4-dihydro-3H-1,2,4-triazolone

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 TRIAZOLE DERIVATIVE;

EID: 0029789069     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960834a     Document Type: Article
Times cited : (73)

References (79)
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    • Krishnan, R.; Frisch, M. J.; Pople, J. A. J. Chem. Phys. 1980, 72. 4244. Bartlett, R. J.; Purvis, G. D. Int. J. Quantum Chem. 1978, 14, 561. Pople, J. A.; Binkley, J. S.; Seeger, R. Int. J. Quantum Chem. Symp. 1976, S10, 1. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
    • (1976) Int. J. Quantum Chem. Symp. , vol.S10 , pp. 1
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    • Krishnan, R.; Frisch, M. J.; Pople, J. A. J. Chem. Phys. 1980, 72. 4244. Bartlett, R. J.; Purvis, G. D. Int. J. Quantum Chem. 1978, 14, 561. Pople, J. A.; Binkley, J. S.; Seeger, R. Int. J. Quantum Chem. Symp. 1976, S10, 1. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
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    • Møller, C.1    Plesset, M.S.2
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    • 2NO has values of 1.265 and 1.223 Å for the CN and NO bond lengths, and 136.1° for the CNO bond angle, compared with the UMP2/6-31G* values of 1.288 Å, 1.318 Å, and 110.3° for these parameters. For QCISD(T) theory see: Raghavachari, K.; Trucks, G. W.; Pople, J. A.; Head-Gordon, M. Chem. Phys. Lett. 1989, 157, 479. Pople, J. A.; Gordon, M. H.; Raghavachari, K. J. Chem. Phys. 1987, 87, 5968.
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    • 2NO has values of 1.265 and 1.223 Å for the CN and NO bond lengths, and 136.1° for the CNO bond angle, compared with the UMP2/6-31G* values of 1.288 Å, 1.318 Å, and 110.3° for these parameters. For QCISD(T) theory see: Raghavachari, K.; Trucks, G. W.; Pople, J. A.; Head-Gordon, M. Chem. Phys. Lett. 1989, 157, 479. Pople, J. A.; Gordon, M. H.; Raghavachari, K. J. Chem. Phys. 1987, 87, 5968.
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    • note
    • 2NO using an active space chosen from the Boy's localized orbitals from an ROHF/6-31G* calculation. In this case the active space was comprised of a three electron/four orbital A' space and a four electron/ three orbital A″ space. The orbitals in the A′ space were nonbonding (i.e., lone pair) orbitals on the nitrogen and oxygen atoms, and the N-O antibonding orbital. The orbitals in the A″ space were an oxygen lone pair, the CN π bond, and the lowest unoccupied A″ orbital. The optimized geometry using the more carefully chosen active space was very similar to the geometry from the first CASSCF calculation. The CN bond length. NO bond length, and CNO angle from the second calculation were respectively 1.286 Å, 1.211 Å, and 131.7°.
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    • CSGT: (a) Keith, T. A.; Bader, R. F. W. Chem. Phys. Lett. 1993. 210, 223. (b) Keith, T. A.; Bader, R. F. W. Chem. Phys. Lett. 1992, 194, 1.
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    • CSGT: (a) Keith, T. A.; Bader, R. F. W. Chem. Phys. Lett. 1993. 210, 223. (b) Keith, T. A.; Bader, R. F. W. Chem. Phys. Lett. 1992, 194, 1.
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    • note
    • The pyramidalization angles for nitrogens N1 and N2 in the B3LYP/ 6-31+G* geometry for structure 7 are respectively 41.8° and 40.3° (these are angles for the NH bond with respect to the CNN plane), which is somewhat smaller than the B3LYP/6-31+G* computed pyramidalization of 67.0° for the nitrogens of hydrazine in its anti conformation. The twisted ring in 7 has a C5-N1-N2-C3 torsion angle of 12.5°.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.