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Rules of Thumb for Assessing Equilibrium Partitioning of Organic Compounds: Successes and Pitfalls

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Kai-Uwe Goss and René P. Schwarzenbach

Swiss Federal Institute for Environmental Science and Technology (EAWAG), Swiss Federal Institute of Technology (ETH), CH-8600 Dübendorf, Switzerland

J. Chem. Educ., 2003, 80 (4), p 450

DOI: 10.1021/ed080p450

Publication Date (Web): April 1, 2003

Section:

History, Education, and Documentation

Abstract

Organic compounds are often categorized according to their volatility, polarity, and hydrophobicity. These terms are then used to estimate the equilibrium partitioning of compounds between different phases (e.g., air, water, organic solvents). However, these terms are rather ill-defined, and their application can easily lead to erroneous ideas about the partition behavior of compounds as is demonstrated with several examples. A simple cavity model of bulk phase partitioning in combination with some basic information about the relevant intermolecular interactions (i.e., van der Waals and H-bond interactions) allows the reader to understand the pitfalls of these widespread misconceptions. This model is further used to derive a number of rules that are better suited for a qualitative estimation of the partition behavior of organic compounds between various bulk phases.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Chemical Education Research

Keywords (Feature):

Research: Science and Education

Keywords (Pedagogy):

Misconceptions / Discrepant Events

Keywords (Subject):

Equilibrium

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This article has been cited by 9 ACS Journal articles (5 most recent appear below).

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  Using historical scientific literature in the classroom has certain advantages. However, a modern reader of such material can be led astray by, among other things, obsolete terminology.
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