RE: ORGLIST:A nomenclature question

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From: Teresa Atkinson (tla$##$eskimo.com)
Date: Thu Dec 04 2003 - 08:59:29 EST


It's R/S, because it's a stereochemical difference.

One way to easily discover this is to install ACD Labs Chemsketch, the
freeware version (no affiliation). You can draw the structure in
Chemsketch. Then if the structure contains 50 atoms or less, freeware
Chemsketch can generate a name for you. ACDLabs works closely with
IUPAC, so their naming is pretty accurate.

When I did the very thing I described above, using
1,2-dimethylcyclohexane

Same side:
(1R,2S)-1,2-dimethylcyclohexane

Opposite side:
(1S,2S)-1,2-dimethylcyclohexane

Find the freeware at http://www.acdlabs.com/download/

Teresa Atkinson
Sammamish, WA

-----Original Message-----
From: everybody-admin$##$orglist.net [mailto:everybody-admin$##$orglist.net]
On Behalf Of Jacob Zabicky

Dear Friends,

What is the correct nomenclature for the relative configuration of two
groups sticking out on the same side or opposite sides of the "plane"
defined by a ring? For example, in 1,2-dimethylcyclohexane.

a. The cis-trans nomenclature is unfit because I use it for double
bonds in the same paragraph.
b. The alpha-beta convention of saccharides or steroids is unfit
because I have no convened representation for the ring system as
reference.
c. Perhaps syn-anti?
d. Perhaps E-Z?
e. Perhaps erythro-threo?
f. Perhaps something else?

An example from published literature, if in hand, would be great.

Thanks in advance,

Jacob

***************************************************
Prof. Jacob Zabicky
Institutes for Applied Research
Ben-Gurion University of the Negev
P. O. Box 653, Beer-Sheva, 84105, Israel

Phone: +972-8-6461271; Fax: +972-8-6472969 zabicky$##$bgumail.bgu.ac.il
http://www.bgu.ac.il/IAR/Zabicky.htm
-------------------------------------------------
Private:
P. O. Box 12366, Beer-Sheva, 84863, Israel
Phone: +972-8-6496792

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