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1 article(s) from Trmčić, Milena

Kinetic studies and predictions on the hydrolysis and aminolysis of esters of 2-S-phosphorylacetates

Milena Trmčić and
David R. W. Hodgson

Beilstein J. Org. Chem. 2010, 6, 732–741, doi:10.3762/bjoc.6.87

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Graphical Abstract

Scheme 1: Use of 2-bromoacetic acid esters as heterobifunctional cross-linking agents.

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Scheme 2: Cross-linking between thiophosphate 4, D-glucosamine (GlcNH₂) and bromoacetyl-N-hydroxybenzotriazol...

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Scheme 3: Ligation of 2-bromoacetic acid esters 1 (R = pNP or mNP) to thiophosphate 4.

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Scheme 4: Displacement of p- or m-nitrophenolate ions from nitrophenyl esters 7 (R = pNP) and 7 (R = mNP).

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Figure 1: log k_hydrol vs pH for the hydrolysis p-nitrophenyl ester 7 (R = pNP) and m-nitrophenyl ester 7 (R = ...

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Figure 2: log k_aminol vs pH for the combined aminolysis and hydrolysis of p-nitrophenyl ester 7 (R = pNP) and ...

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Scheme 5: Kinetic model for competing hydrolysis and aminolysis processes of nitrophenyl esters 7 (R = pNP) a...

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Figure 3: Predicted concentration-time profile for the reaction between starting concentrations of 0.05 M p-n...

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Figure 4: Predicted concentration-time profile for the reaction between starting concentrations of 0.05 M m-n...

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Figure 5: Predicted leaving group pK_aH values required for user-defined conversion levels of starting concent...

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Scheme 6: (A) Direct aminolysis of the ester carbonyl group; (B) intramolecular nucleophilic catalysis of est...

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Figure 6: 2-nitrophenyl 2-(ethylthio)acetate.

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Full Research Paper

Published 16 Aug 2010

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