38319-29-8

Upstream product

• 554-84-7 meta-nitrophenol 

Downstream Products

• 4532-06-3 O,O-diethyl O-(3-nitrophenyl)-phosphate 
• 13388-91-5 3-nitrophenyl phosphate 
• 115142-13-7 Phosphoric acid (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(tetrahydro-pyran-2-yloxy)-2-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-3-yl ester 3-nitro-phenyl ester 
• 115142-03-5 Phosphoric acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl ester 3-nitro-phenyl ester 
• 54113-51-8 Phosphoramidic acid methyl ester 3-nitro-phenyl ester 

Relevant academic research and scientific papers

Charge Description of Base-Catalyzed Alcoholysis of Aryl Phosphodiesters: A Ribonuclease Model

The release of substituted phenol from aryl uridine-3'-phosphates is catalyzed by bases and involves cyclization to form the 2',3'-cyclic nucleotide.The rate constants for imidazole and hydroxide ion catalysis (kim and kOH, respectively) obey the Broensted equations (25 deg C and 0.25 M ionic strength) log kim = -0.59 pKArOH + 1.40 (n = 7, r = 0.955) and log kOH = -0.54 pKArOH + 6.68 (n = 9, r = 0.967).General-base-catalyzed release of 4-nitrophenol from the 4-nitrophenyl ester (kB) obeys the Broensted relationship log kB = 0.67 pKBH - 7.50 (n = 7, r = 0.989).Charge changes on base and leaving group atoms as determined from the corresponding β and βeq values do not balance.Comparison with data in the literature indicates that the difference in charge may be assigned to the attacking oxygen (2'-hydroxyl) rather than to the phosphoryl oxygens in the O...PO2... group of atoms.Both P-O bond forming and bond fission components of the reaction are considered to be only weakly advanced in a transition state that lies on a concerted pathway.

Mechanism of Hydrolysis of Phosphorylethanolamine Diesters. Intramolecular Nucleophilic Amine Participation

Intramolecular displacement reactions at phosphorus have been examined in a series of N-alkyl-O-arylphosphorylethanolamines in water at 35 deg C.The examination of the pH-rate profiles and the direct observation by 31P n.m.r. of the reaction products implicate a nucleophilic role for the amine.A rate enhancement of 1E6-1E7 is observed.Structure-reactivity correlations derived by changing the pKa of the amine and leaving group yield values for βnuc 0.7 and βlg -1.25 and support an uncoupled concerted mechanism.A discussion of the mechanisms of nucleophilic reactions involving amines and oxyanions with inter- and intra-molecular phosphate di- and tri-esters is presented.