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Volumn 122, Issue 10, 2000, Pages 2145-2148

The substrate-assisted general base catalysis model for phosphate monoester hydrolysis: Evaluation using reactivity comparisons

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; PHOSPHATE;

EID: 0034654214     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993942g     Document Type: Article
Times cited : (66)

References (47)
  • 16
    • 0343640299 scopus 로고    scopus 로고
    • note
    • Abbreviations: DNPP, 2,4-dinitrophenyl phosphate; MDNPP, methyl 2,4-dinitrophenyl phosphate; BDNPP, bis-2,4-dinitrophenyl phosphate; pNPP, p-nitrophenyl phosphate; pNPPS, p-nitrophenyl phosphorothioate.
  • 20
    • 0342335127 scopus 로고    scopus 로고
    • taut (39°C)
    • taut (39°C).
  • 28
    • 0342335126 scopus 로고    scopus 로고
    • note
    • a of the 2,4-dinitrophenol leaving group renders bond scission without proton transfer favorable.
  • 32
    • 0343640264 scopus 로고    scopus 로고
    • HO-)
    • HO-).
  • 35
    • 0342335100 scopus 로고    scopus 로고
    • note
    • It is important to note that the hydrolysis of ethyl phosphate dianion could still occur via the alkyl phosphate monoanion and hydroxide ion in a fashion consistent with the classical mechanism (eq 1). Such a pathway would be favored if the advantage from proton transfer to the leaving group and the modest increase in reactivity for hydroxide ion relative to water compensated for the lower concentrations of these species relative to the alkyl phosphate dianion and water. This possibility is currently under investigation. Regardless, the observed thio effect suggests that the proton does not remain on the transferred phosphoryl group in the transition state, as postulated in the substrate-assisted catalysis mechanism.
  • 44
    • 0000546527 scopus 로고
    • (d) Friedman, J. M.; Freeman, S.; Knowles, J. R. J. Am. Chem. Soc. 1988, 110, 1268-1275. See also Hengge et al. (Hengge, A. C.; Edens, W. A.; Elsing, H. J. Am. Chem. Soc. 1994, 116, 5045-5049) and ref 15b.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 1268-1275
    • Friedman, J.M.1    Freeman, S.2    Knowles, J.R.3
  • 45
    • 0001158302 scopus 로고
    • Hengge, A. C.; Edens, W. A.; Elsing, H. and ref 15b
    • (d) Friedman, J. M.; Freeman, S.; Knowles, J. R. J. Am. Chem. Soc. 1988, 110, 1268-1275. See also Hengge et al. (Hengge, A. C.; Edens, W. A.; Elsing, H. J. Am. Chem. Soc. 1994, 116, 5045-5049) and ref 15b.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 5045-5049
    • Hengge1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.