Display options
Cite
Kirby AJ, Lima MF, da Silva D, et al. Nucleophilic attack by oxyanions on a phosphate monoester dianion: the positive effect of a cationic general Acid. J Am Chem Soc. 2004;126(5):1350-1doi: 10.1021/ja038428w.
Kirby, A. J., Lima, M. F., da Silva, D., & Nome, F. (2004). Nucleophilic attack by oxyanions on a phosphate monoester dianion: the positive effect of a cationic general Acid. Journal of the American Chemical Society, 126(5), 1350-1. https://doi.org/10.1021/ja038428w
Kirby, Anthony J, et al. "Nucleophilic attack by oxyanions on a phosphate monoester dianion: the positive effect of a cationic general Acid." Journal of the American Chemical Society vol. 126,5 (2004): 1350-1. doi: https://doi.org/10.1021/ja038428w
Kirby AJ, Lima MF, da Silva D, Nome F. Nucleophilic attack by oxyanions on a phosphate monoester dianion: the positive effect of a cationic general Acid. J Am Chem Soc. 2004 Feb 11;126(5):1350-1. doi: 10.1021/ja038428w. PMID: 14759187.
Copy Download .nbib Format: NLM
Share it on

J Am Chem Soc. 2004 Feb 11;126(5):1350-1. doi: 10.1021/ja038428w.

Nucleophilic attack by oxyanions on a phosphate monoester dianion: the positive effect of a cationic general Acid.

Journal of the American Chemical Society

Anthony J Kirby, Marcelo F Lima, Davi da Silva, Faruk Nome

Affiliations

  1. University Chemical Laboratory, Cambridge University, Cambridge CB2 1EW, UK. [email protected]

PMID: 14759187 DOI: 10.1021/ja038428w

Abstract

The two negative charges on a phosphate monoester RO-PO32- at neutral pH provide a considerable electrostatic barrier toward reactions with nucleophilic reagents with a negative charge on the attacking atom. Electrostatic repulsion disappears when the hydrolysis of an aryl phosphate monoester is catalyzed by a neighboring cationic general acid. The hydrolysis of 8-dimethylammonium-1-phosphate (1) is catalyzed by oxyanions, fluoride anion, and hydroxylamines at similar rates.

Publication Types