Change of the Hydrolytic Mechanism of 2-Hydroxy H-Phosphonodiesters in Aprotic Organic Media. cis-1,2-Diol Monoanions as Leaving Groups

Autor:	Rositza T. Momtcheva, Svetomir B. Tzokov, and Jose Kaneti, Nikolay G. Vassilev, Dimiter D. Petkov
Rok vydání:	1999
Předmět:	Aqueous solution Hydrogen bond Diol Oxyanion General Chemistry Biochemistry Organic media Medicinal chemistry Catalysis chemistry.chemical_compound Hydrolysis Colloid and Surface Chemistry chemistry Vicinal
Zdroj:	Journal of the American Chemical Society. 121:5103-5107
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja982413u
Popis:	The hydrolysis of H-phosphonodiesters bearing a vicinal hydroxyl group is found to be subject to two competing reaction pathways in aprotic organic media. An observation of the increased proportion of cis-1,2-diol leaving with decrease of the water content is interpreted in terms of a change of the hydrolytic mechanism on changing the reaction medium from aqueous to nonaqueous. The hydroxyl group in cis-1,2-diol monoanions hydrogen bonds strongly to the adjacent oxyanion, implying a low-energy route closely related to reactions, catalyzed by large ribozymes.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::834a65a30997b4ca4fca5f09bf8d4453 https://doi.org/10.1021/ja982413u Zobrazit plný text záznamu