ORGLIST:re: A Rookie Question

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From: Paul D. Jones (pdjones$##$ucdavis.edu)
Date: Thu Feb 19 2004 - 11:45:35 EST


Teresa,

First, I applaud your efforts to find the answers to a puzzling
observation, keep it up!

Second, I spent a great deal of time synthesizing and manipulating trityl
(triphenyl methane) compounds, here are some thoughts on your question:

You are correct to surmise that the color should have in fact gone from a
deep red to a yellowish tint. This is typically associated with the
quenching of the Mg2+ stabilized anion which is formed in during the
reaction. It has been my experience though, that this is not always the
case. One possibility is that there are impurities in your reaction which
could interact either with the hydroxyl group or with the phenyl rings
which may induce a shift in color. considering that you melting point is 10
C below the literature mp (161-163C), your sample is not 100%
pure. Additional recrystallizations or silica chromatography will help.

As an afterthought, I have often found that reliance on color in organic
reactions can often be misleading (except when one works with transition
metals). it does not take a lot of impurity to alter the appearance of the
product.

Hope this helps.

-paul

================================
Paul D. Jones, Ph.D.
Department of Entomology &
Cancer Research Center
University of California
Davis, CA 95616 USA
(530) 754-8884
================================

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