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Topic: 2-hydroxypropanenitrile  (Read 7511 times)

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Offline scarletthj

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2-hydroxypropanenitrile
« on: April 28, 2009, 06:23:05 AM »
Hello,

I am having trouble with an assignment.

There are 2 questions i am stuck on which are ~

1. Explain why one isomer of 2-hydroxypropanenitrile is likely to be more toxic than the other

2. Inorganic cyanide in the form of K+ CN- is much more toxic than 2-hydroxypropanenitrile. The cyanide bonds with haemoglobin in blood replacing bonded oxygen and causing death.
Explain the difference in toxicity between the 2 substances.

If anyone can help i would be most grateful!

Thank you.

Offline sjb

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Re: 2-hydroxypropanenitrile
« Reply #1 on: April 28, 2009, 08:35:41 AM »
Why is one isomer of any compound likely to have a different effect in vivo than another?

What are the main differences between the cyanide group in KCN and in 2-hydroxypropanenitrile?

Offline scarletthj

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Re: 2-hydroxypropanenitrile
« Reply #2 on: April 28, 2009, 01:31:46 PM »
I think the answer is something to do with the 3D shape connecting to the enzyme molecules?

I'm really struggling on this one.

Offline Mitch

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Re: 2-hydroxypropanenitrile
« Reply #3 on: April 28, 2009, 02:36:42 PM »
1.) Think R and S stereochemistry.
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Offline scarletthj

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Re: 2-hydroxypropanenitrile
« Reply #4 on: April 28, 2009, 04:46:15 PM »
ok, so i think that the arrangement of the atoms differ in the isomers - one is an R configuration and one is an S.

But how does this affect it's toxicity? and which one is the toxic one?

How do i find this information?

Thanks for helping.


Offline Mitch

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Re: 2-hydroxypropanenitrile
« Reply #5 on: April 28, 2009, 05:03:58 PM »
It would be odd if you had to know which one is more toxic. I think the question was asking in general terms why a given enantiomer would be more toxic.

http://en.wikipedia.org/wiki/Chirality_(chemistry)#In_biology
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Offline sjb

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Re: 2-hydroxypropanenitrile
« Reply #6 on: April 29, 2009, 03:30:59 AM »
It would be odd if you had to know which one is more toxic.

Agreed to that, perhaps at a higher level you might need to know which enantiomer. Anyway I think you have the essence of the answer, a nuance though - what are the breakdown products, are any of them toxic / involved anywhere in vivo? (You may not need to know this, so feel free to ignore ;) )

Offline scarletthj

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Re: 2-hydroxypropanenitrile
« Reply #7 on: April 29, 2009, 05:51:01 AM »
Thanks to those who helped me, i think i have got the answer sorted now!

I appreciate your help.

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