Nucleophilic Attack by Oxyanions on a Phosphate Monoester Dianion: The Positive Effect of a Cationic General Acid

Journal of the American Chemical Society

Volumn 126, Issue 5, 2004, Pages 1350-1351

  Kirby, Anthony J ^a   Lima, Marcelo F ^b   Da Silva, Davi ^b   Nome, Faruk ^b  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYL PHOSPHATE; ADENOSINE TRIPHOSPHATE; ANION; ESTER DERIVATIVE; FLUORIDE; ORGANOPHOSPHATE; OXYANION; PHOSPHATE; PHOSPHATE ESTER DIANION; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ELECTRICITY; HYDROGEN BOND; HYDROLYSIS; PH;

EID: 1042288184     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja038428w     Document Type: Article

References (16)

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10. Asaad, N.; Kirby, A. J. J. Chem. Soc. Perkin Trans. 2 2002, 1708-1712.
11. a's are shifted substantially as compared to those for similar unperturbed groups, consistent with a strong intramolecular hydrogen bond between them in the ground state. This hydrogen bond plays a significant role in enabling anion attack, even though stabilization of the reactant will in general reduce the extent of general acid catalysis.
12. Kirby, A. J.; Dutta-Roy, N.; da Silva, D.; Lima, M. F.; Nome, F. to be published.
13. Khan, S. A.; Kirby, A. J. J. Chem. Soc. B 1970, 1172-1182.
14. Kirby, A. J.; Younas, M. J. Chem. Soc. B 1970, 1165-1172.
15. rel for the di- and triesters.
16. Bromilow, R. H.; Kirby, A. J. J. Chem. Soc. B 1972, 149-155.