Literature DB >> 15901142

Solvent effect on concertedness of the transition state in the hydrolysis of p-nitrophenyl acetate.

Daiqian Xie1, Yanzi Zhou, Dingguo Xu, Hua Guo.   

Abstract

[reaction: see text]. The reaction pathway for the alkaline hydrolysis of p-nitrophenyl acetate is investigated using density functional theory. It is shown that solvent plays an indispensable role in shaping the concerted transition state. The concertedness of this transition state is supported by good agreement with the measured kinetic isotope effects.

Entities:  

Year:  2005        PMID： 15901142     DOI： 10.1021/ol0502836

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  5 in total

1.  Concerted or stepwise: how much do free-energy landscapes tell us about the mechanisms of elimination reactions?

Authors:  Fernanda Duarte; Scott Gronert; Shina Caroline Lynn Kamerlin
Journal:  J Org Chem       Date:  2014-01-24       Impact factor: 4.354

2.  Intramolecular Tricarbonyl-Ene Reactions and α-Hydroxy-β-Diketone Rearrangements Inspired by the Biosynthesis of Polycyclic Polyprenylated Acylphloroglucinols.

Authors:  Andreas B Zur Bonsen; Ricardo A Peralta; Thomas Fallon; David M Huang; Jonathan H George
Journal:  Angew Chem Int Ed Engl       Date:  2022-07-14       Impact factor: 16.823

3.  The alkaline hydrolysis of sulfonate esters: challenges in interpreting experimental and theoretical data.

Authors:  Fernanda Duarte; Ting Geng; Gaël Marloie; Adel O Al Hussain; Nicholas H Williams; Shina Caroline Lynn Kamerlin
Journal:  J Org Chem       Date:  2013-12-06       Impact factor: 4.354

4.  Probing the mechanisms for the selectivity and promiscuity of methyl parathion hydrolase.

Authors:  Miha Purg; Anna Pabis; Florian Baier; Nobuhiko Tokuriki; Colin Jackson; Shina Caroline Lynn Kamerlin
Journal:  Philos Trans A Math Phys Eng Sci       Date:  2016-11-13       Impact factor: 4.226

5.  Modeling the Alkaline Hydrolysis of Diaryl Sulfate Diesters: A Mechanistic Study.

Authors:  Klaudia Szeler; Nicholas H Williams; Alvan C Hengge; Shina C L Kamerlin
Journal:  J Org Chem       Date:  2020-04-30       Impact factor: 4.354
  5 in total

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