Qualitative understanding of partition preferences

Introduction
Cavity model
     A simple model for bulk phase partitioning
     The cavity approach
     The interaction energies
     Polarity
     Exercise
Rules for partitioning
The cavity model in quantitative terms

Selftest
Problems
Intermolecular interactions in every day life
FAQ

Polarity

From the above information on intermolecular interactions it follows that a simple distinction between non-polar and polar molecules is not sufficient. Instead we must distinguish between molecules that are apolar (i.e. neither H−bond donor nor H−bond acceptor), monopolar (either H−bond donor or H−bond acceptor), or bipolar (both H−bond donor and H−bond acceptor). A classification of a compound can usually already be done when its structural formula is known, for example:

  • All compounds that contain an H−atom in form of a −OH or −NH group are H−bond donors.
  • Compounds containing oxygen or nitrogen are strong H−bond acceptors.
  • Compounds with pi−electrons are weak H-bond acceptors.

Table: Examples for the different abilities of organic compounds to interact by van der Waals and H−bond interactions.

apolar compounds

monopolar compounds

bipolar comp.1

only van der Waals
interactions

van der Waals +
H-bond acceptor
(e-donor)

van der Waals +
H-bond donor
(e-acceptor)

van der Waals +
H-bond donor +
H-bond acceptor

alkanes
chlorobenzenes2
PCBs2

alkenes, alkynes,
alkylaromatic compounds,
ethers, ketones,
esters, aldehydes

CHCl3
CH2 Cl2

R − NH2
R2− NH
R − COOH
R − OH


1 Intramolecular H-bonds like in 2-nitrophenol strongly reduce the ability of the compound to form H−bonds with neighboring molecules.
2 Compounds whose pi-electron density is diminished by electron withdrawing substituents are apolar.

 

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