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Determination of Hammett Equation Rho Constant for the Hydrolysis of p-Nitrophenyl Benzoate Esters

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Sheue L. Keenan , Karl P. Peterson , Kelly Peterson and Kyle Jacobson

Department of Chemistry, University of Wisconsin–River Falls, River Falls, WI 54022

J. Chem. Educ., 2008, 85 (4), p 558

DOI: 10.1021/ed085p558

Publication Date (Web): April 1, 2008

Abstract

Seven p-nitrophenyl benzoate esters (p-nitrophenyl benzoate, p-nitrophenyl m-anisate, p-nitrophenyl p-anisate, p-nitrophenyl m-chlorobenzoate, p-nitrophenyl p-chlorobenzoate, p-nitrophenyl m-toluate, p-nitrophenyl p-toluate) were synthesized and characterized by students in a second-semester organic laboratory course. In a subsequent laboratory period, the rate constants for the base hydrolysis of these esters were measured by monitoring the formation of the p-nitrophenoxide ion by UV-vis spectrophotometry. The Hammett equation rho (ρ) constant for this hydrolysis reaction was then determined. The two-experiment sequence was developed to demonstrate structure–reactivity relationships and pseudo-first-order reaction kinetics. The students gained experience in organic synthesis and characterization, performing kinetics studies by spectrophotometry, and carrying out data analysis using spreadsheet software.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Aromatic Compounds

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

Modeling the Geometric, Electronic, and Redox Properties of Iron(III)-Containing Amphiphiles with Asymmetric [NN′O] Headgroups
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Inorganic Chemistry2011 Article ASAP
- Modeling the Geometric, Electronic, and Redox Properties of Iron(III)-Containing Amphiphiles with Asymmetric [NN′O] Headgroups
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  Two iron(III)-containing amphiphiles 1 and 2 have been synthesized with the [NN′O] ligands HLtBu-ODA (2-((octadecyl(pyridin-2-ylmethyl)amino)methyl)-4,6-di-tert-butylphenol) and HLI-ODA (2-((octadecyl(pyridin-2-ylmethyl)amino)methyl)-4,6-diiodophenol), ...
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Hammett Parameter and Molecular-Modeling Correlations of Substituent Effects on Esterification Kinetics
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Journal of Chemical Education2010 87 (8), 845-847
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  Jeremy B. Smith, Houston Byrd, Stephen E. O’Donnell and Will Davis
  Journal of Chemical Education2010 87 (8), 845-847
  The effect of substituents on the rate of reactions is taught extensively throughout organic chemistry. The Hammett equation is useful in quantifying this dependence; however, there are relatively few experiments that investigate this relationship. We ...
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