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Volumn 69, Issue 13, 2004, Pages 4309-4316

Rationale for the acidity of Meldrum's acid. Consistent relation of C-H acidities to the properties of localized reactive orbital

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; CHEMICAL BONDS; CONFORMATIONS; MOLECULAR STRUCTURE; PROTONS;

EID: 3042704685     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049456f     Document Type: Article
Times cited : (74)

References (30)
  • 18
    • 0027219071 scopus 로고
    • (a) Ohwada, T. Tetrahedron 1993, 49, 7649-7656.
    • (1993) Tetrahedron , vol.49 , pp. 7649-7656
    • Ohwada, T.1
  • 20
    • 3042759680 scopus 로고    scopus 로고
    • note
    • CH orbital is an antibonding orbital of carbon and hydrogen atomic orbitals, electron delocalization to the present orbital leads to C-H bond cleavage. Other remaining components also interact with the major component to influence the reactivity. Construction of the reactive orbital of deprotonation of carbonyl compounds: (Diagram presented).
  • 21
    • 3042752720 scopus 로고    scopus 로고
    • note
    • Regression coefficient of Figure 4: r = 0.783.
  • 22
    • 3042750439 scopus 로고    scopus 로고
    • note
    • Regression coefficient of Figure 5: r = 0.924. When the data for 7 and 8 are excluded, the regression coefficient increases: r = 0.993. Similarly when 7 and 8 are excluded in Figure 5, the regression coefficient is r = 0.835.
  • 23
    • 3042711768 scopus 로고    scopus 로고
    • note
    • i.
  • 25
    • 3042795804 scopus 로고    scopus 로고
    • note
    • All the calculated transition structures involved coordination of the lithium cation to the oxygen atom of the carbonyl or ether group. In the case of dimethyl malonate 7, only the Li-bidentate-type transition structure was found, whereas the monodentate-type structures were obtained in the cases of 1, 5, 6, and 8.
  • 26
    • 3042831685 scopus 로고    scopus 로고
    • note
    • unoc from the values of the stable structures.) 1, 131.7 (+4.1); 5, 138.7 (+0.5); 6, 137.2 (-0.3); 7, 153.5 (-11.1); 8, 143.5 (-16.6).
  • 27
    • 3042791243 scopus 로고    scopus 로고
    • note
    • unoc values of the activated structures were used.)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.