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Volumn 69, Issue 26, 2004, Pages 9248-9254

Reactions of substituted (methylthio)benzylidene Meldrum's acids with secondary alicyclic amines in aqueous DMSO. Evidence for rate-limiting proton transfer

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; AROMATIC HYDROCARBONS; CATALYSIS; CHEMICAL BONDS; ORGANIC ACIDS; SUBSTITUTION REACTIONS;

EID: 10844262562     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo040244s     Document Type: Article
Times cited : (14)

References (50)
  • 5
    • 0347545735 scopus 로고
    • (d) Rappoport, Z. Acc. Chem. Res. 1981, 14, 7; 1992, 25, 474.
    • (1992) Acc. Chem. Res. , vol.25 , pp. 474
  • 18
    • 10844238927 scopus 로고    scopus 로고
    • note
    • At high pH this condition is easily met.
  • 31
    • 10844296628 scopus 로고    scopus 로고
    • note
    • See paragraph concerning Supporting Information at the end of this paper.
  • 32
    • 10844234029 scopus 로고    scopus 로고
    • note
    • +-catalyzed leaving group departure. However, these terms are negligible in the pH range used for this study.
  • 33
    • 10844290802 scopus 로고    scopus 로고
    • note
    • w = 15.89 in 50% DMSO-50% water (v/v) at 20 °C.
  • 37
    • 10844293452 scopus 로고    scopus 로고
    • note
    • ± below that for diffusion control. Such an effect cannot be excluded even though this hydrogen bond is likely to be weak due to the very low basicity of the enolate oxygen. More importantly, even if there is some rate reduction due to hydrogen bonding, this does not affect any of our conclusions.
  • 38
    • 10844261692 scopus 로고    scopus 로고
    • note
    • a of Meldrum's acid in 50% DMSO-50% water (v/v) at 20 °C is 4.70.
  • 41
    • 10844271503 scopus 로고    scopus 로고
    • note
    • Such steric reductions have been observed in cases where the proton-transfer rate constants were directly measurable.
  • 45
    • 10844230220 scopus 로고    scopus 로고
    • note
    • a of MeSH in water is 10.33; in 50% DMSO-50% water it is estimated to be close to 11.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.