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Volumn 131, Issue 1, 2009, Pages 368-377

Dissociative solvolytic cleavage of methyl (ortho-Carboxymethyl)Aryl phosphate diesters mediated by Yb3+ in methanol gives a 10 12-fold rate acceleration attributable to leaving group assistance

Author keywords

[No Author keywords available]

Indexed keywords

ARYL GROUP; ARYL PHOSPHATE; BINDING CONSTANT; CARBOXYMETHYL; CATALYTIC RATES; CATALYZED REACTIONS; CLEAVAGE REACTION; CONTROL STUDIES; DIMETHYL PHOSPHATES; LEAVING GROUPS; LOW CONCENTRATIONS; POSITIVE CHARGES; RATE ACCELERATION; RATE OF REACTION; REACTION PRODUCTS; TRANSITION STATE;

EID: 62649117399     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja807984f     Document Type: Article
Times cited : (17)

References (78)
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    • -4 M removes this ambiguity.
    • -4 M removes this ambiguity.
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    • The fact that there is more than one aryl substituent involved in the catalysis of phosphate esters 2a-h necessitates the use of the Jaffe equation as opposed to the more common Brønsted relationship. The reaction constants obtained from the Jaffe plot can be converted to a Brønsted slope using the relationship β, p × δσ/δsspKa
    • a.
  • 47
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    • 4- bound between two Co(III) centers, it appears that two metal ions have the effect of a single proton. By extension, a single metal ion is predicted to have the effect of 1/2 a proton: (a) Edwards, J. D.; Foong, S.-W.; Sykes, A. G. J. Chem. Soc., Dalton Trans. 1973, 829.
    • 4- bound between two Co(III) centers, it appears that two metal ions have the effect of a single proton. By extension, a single metal ion is predicted to have the effect of 1/2 a proton: (a) Edwards, J. D.; Foong, S.-W.; Sykes, A. G. J. Chem. Soc., Dalton Trans. 1973, 829.
  • 62
    • 67849093622 scopus 로고    scopus 로고
    • MeOH and the linear relationship between them as described in the Experimental Section under the heading Methods.
    • MeOH and the linear relationship between them as described in the Experimental Section under the heading Methods.
  • 63
    • 37049122234 scopus 로고    scopus 로고
    • 3-catalyzed methanolysis of 2a can be corrected upwards by this amount Kirby, A. J.; Younas, M. J. Chem. Soc. B 1970, 1165.
    • 3-catalyzed methanolysis of 2a can be corrected upwards by this amount Kirby, A. J.; Younas, M. J. Chem. Soc. B 1970, 1165.
  • 68
    • 21844455264 scopus 로고    scopus 로고
    • (e) Weston, J. Chem. Rev. 2006, 105, 2151.
    • (2006) Chem. Rev , vol.105 , pp. 2151
    • Weston, J.1
  • 78
    • 67849123639 scopus 로고    scopus 로고
    • -1 at 45 °C (ref 39).
    • -1 at 45 °C (ref 39).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.