Literature DB >> 24377055

Evaluation of Electronic Effects in the Solvolyses of p-Methylphenyl and p-Chlorophenyl Chlorothionoformate Esters.

Malcolm J D'Souza1, Olivia N Hampton1, Brett M Sansbury1, Dennis N Kevill2.   

Abstract

The solvolyses of p-tolyl chlorothionoformate and p-chlorophenyl chlorothionoformate are studied in a variety of organic mixtures of widely varying nucleophilicity and ionizing power values. This solvolytic data is accumulated at 25.0 °C using the titration method. An analysis of the rate data using the extended (two-term) Grunwald-Winstein equation, and the concept of similarity of substrates based on their l/m ratios, shows the occurrence of simultaneous side-by-side addition-elimination and unimolecular SN1 mechanisms.

Entities:  

Keywords:  Grunwald-Winstein equation; Solvolysis; addition-elimination; ionization; p-chlorophenyl chlorothionoformate; p-tolyl (or p-methylphenyl) chlorothionoformate

Year:  2013        PMID： 24377055      PMCID： PMC3873162          DOI： 10.1155/2013/248534

Source DB:  PubMed          Journal:  J Chem        ISSN： 2090-9071


  24 in total

1.  Correlation of the rates of solvolysis of cyclopropylcarbinyl and cyclobutyl bromides using the extended Grunwald-Winstein equation

Authors: 
Journal:  J Org Chem       Date:  2000-04-21       Impact factor: 4.354

2.  Rate and product studies with benzyl and p-nitrobenzyl chloroformates under solvolytic conditions

Authors: 
Journal:  J Org Chem       Date:  2000-11-17       Impact factor: 4.354

3.  Design, synthesis and antitumor evaluation of novel thalidomide dithiocarbamate and dithioate analogs against Ehrlich ascites carcinoma-induced solid tumor in Swiss albino mice.

Authors:  Magdy A-H Zahran; Tarek A-R Salem; Rehab M Samaka; Hussein S Agwa; Ayman R Awad
Journal:  Bioorg Med Chem       Date:  2008-10-02       Impact factor: 3.641

4.  Use of empirical correlations to determine solvent effects in the solvolysis of S-methyl chlorothioformate.

Authors:  Malcolm J D'Souza; Stefan M Hailey; Dennis N Kevill
Journal:  Int J Mol Sci       Date:  2010-05-25       Impact factor: 5.923

5.  Kinetics and mechanisms of the pyridinolysis of phenyl and 4-nitrophenyl chlorothionoformates. Formation and hydrolysis of 1-(aryloxythiocarbonyl)pyridinium cations.

Authors:  Enrique A Castro; María Cubillos; José G Santos
Journal:  J Org Chem       Date:  2004-07-09       Impact factor: 4.354

6.  Structural effects on the solvolytic reactivity of carboxylic and sulfonic acid chlorides. Comparisons with gas-phase data for cation formation.

Authors:  T William Bentley
Journal:  J Org Chem       Date:  2008-07-17       Impact factor: 4.354

7.  Kinetic evaluation of the solvolysis of isobutyl chloro- and chlorothioformate esters.

Authors:  Malcolm J D'Souza; Matthew J McAneny; Dennis N Kevill; Jin Burm Kyong; Song Hee Choi
Journal:  Beilstein J Org Chem       Date:  2011-04-29       Impact factor: 2.883

8.  Solvolyses of benzoyl chlorides in weakly nucleophilic media.

Authors:  Thomas William Bentley; Haldon Carl Harris
Journal:  Int J Mol Sci       Date:  2011-07-28       Impact factor: 5.923

9.  A Study of Solvent Effects in the Solvolysis of Propargyl Chloroformate.

Authors:  Malcolm J D'Souza; Anthony M Darrington; Dennis N Kevill
Journal:  ISRN Org Chem       Date:  2011

10.  Use of Linear Free Energy Relationships (LFERs) to elucidate the mechanisms of reaction of a γ-methyl-β-alkynyl and an ortho-substituted aryl chloroformate ester.

Authors:  Malcolm J D'Souza; Jaci A Knapp; Gabriel A Fernandez-Bueno; Dennis N Kevill
Journal:  Int J Mol Sci       Date:  2012-01-10       Impact factor: 6.208
View more
  1 in total

1.  Influence of sulfur for oxygen substitution in the solvolytic reactions of chloroformate esters and related compounds.

Authors:  Malcolm J D'Souza; Dennis N Kevill
Journal:  Int J Mol Sci       Date:  2014-10-10       Impact factor: 5.923
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.