From owner-chemistry@ccl.net Thu Oct  4 15:05:00 2007
From: "Nuno A. G. Bandeira nuno.bandeira++ist.utl.pt" <owner-chemistry(0)server.ccl.net>
To: CCL
Subject: CCL: Quantitative measure for susceptibility to nucleophilic attack?
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X-Original-From: "Nuno A. G. Bandeira" <nuno.bandeira ~ ist.utl.pt>
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Date: Thu, 04 Oct 2007 19:31:44 +0100
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Sent to CCL by: "Nuno A. G. Bandeira" [nuno.bandeira . ist.utl.pt]
Seth Olsen s.olsen1/./uq.edu.au wrote:
> 
> I am interested in techniques which can provide a measure of 
> susceptibility to nucleophilic attack in a particular fragment across a 
> series of molecules. The goal is to have a quantitative measure of how 
> different substitutents at another site affect the likelihood of 
> nucleophilic attack at the site of interest.
> 
> This is somewhat removed from the areas of electronic structure to which 
> I am accustomed. I understand from reading Bader's book that divots and 
> bumps in the lapacian of the density can be an indication of these, but 
> I was wondering if there was something a little more straightforward to 
> analyze.

There's Fukui's condensed nucleophilic/electrophilic functions which are 
derived from chemical hardness principles.
In principle what you seek can be extracted from the electronic density.

You'll find it in Pearson's "Chemical Hardness" published by Wiley or 
any good review on the subject.


-- 
Nuno A. G. Bandeira, AMRSC
Graduate researcher and molecular sculptor
Inorganic and Theoretical Chemistry Group,
Faculty of Science
University of Lisbon - C8 building, Campo Grande,
1749-016 Lisbon,Portugal
http://cqb.fc.ul.pt/intheochem/nuno.html
Doctoral student % IST,Lisbon
--