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Volumn 122, Issue 2, 2000, Pages 390-391

Stereochemistry of the Furan-Maleic anhydride cycloaddition: A theoretical study

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; FURAN; MALEIC ANHYDRIDE;

EID: 0343986397     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9913028     Document Type: Article
Times cited : (31)

References (30)
  • 8
    • 0342390713 scopus 로고    scopus 로고
    • note
    • 1H NMR, following the evolution of the integrals corresponding to the hydrogens a to the oxygen bridge of the endo (5.43 ppm) and exo (5.34 ppm) [4+2] adducts. According to these results, the endo adduct is formed slightly faster than the exo one, resulting in a difference in the activation energy of 0.20 kcal/mol, which seems to be in sharp disagreement with the previous results of Lee and Herndon in ref 4 (personal communication from F. J. González).
  • 13
    • 0004133516 scopus 로고    scopus 로고
    • Gaussian, Inc.: Pittsburgh, PA
    • (a) Frisch, M. J. et al. Gaussian 94; Gaussian, Inc.: Pittsburgh, PA, 1995.
    • (1995) Gaussian 94
    • Frisch, M.J.1
  • 14
    • 0004133516 scopus 로고    scopus 로고
    • Gaussian, Inc.: Pittsburgh, PA
    • (b) Frisch, M. J. et al. Gaussian 98; Gaussian, Inc.: Pittsburgh, PA, 1998.
    • (1998) Gaussian 98
    • Frisch, M.J.1
  • 15
    • 0342825470 scopus 로고    scopus 로고
    • note
    • Due to computational shortcomings, QCISD(T) or CCSD(T) energies were not obtained for the furan + maleic anhydride reaction. Nonetheless, we note that the MP4/6-31G*//MP2/6-31G* electronic energies for the energy barrier (22.3 kcal/mol) and reaction energy (-42.3 kcal/mol) of the 1,3-butadiene + ethylene Diels - Alder reaction compare reasonably well with those at QCISD(T)/6-31G*//MP2/6-31G* (25.0 and -40.6 kcal/mol, respectively).
  • 16
    • 0343695975 scopus 로고    scopus 로고
    • note
    • MP2/6-31G*.
  • 18
    • 0342390708 scopus 로고    scopus 로고
    • note
    • 8 Mulliken overlap populations in the endo TS have values of -0.01 (MP2) and 0.00 e (B3LYP).
  • 25
    • 0342825469 scopus 로고    scopus 로고
    • note
    • HF/6-31G* results are very similar to those at B3LYP/6-31G*, the endo TS being thus oniy 0.05 kcal/mol more stable than the exo one. This negligible HF stereoselectivity for the furan + maleic anhydride cycloaddition in the gas phase is in consonance with the proposed role played by dispersion interactions (absent in both HF and B3LYP calculations) stabilizing the endo TS.
  • 26
    • 0000545699 scopus 로고
    • Gaussian Basis Sets and Molecular Integrals
    • Yarkony, D. R., Ed.; World Scientific: Singapore
    • Helgaker, T.; Taylor, P. R. Gaussian Basis Sets and Molecular Integrals. In Modern Electronic Structure Theory Part II; Yarkony, D. R., Ed.; World Scientific: Singapore, 1995.
    • (1995) Modern Electronic Structure Theory Part II
    • Helgaker, T.1    Taylor, P.R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.