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Topic: Question on correct chemical structure  (Read 348 times)

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Offline LightningShotz

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Question on correct chemical structure
« on: June 17, 2020, 07:05:00 AM »
Hi

Please redirect if I have submitted in the wrong location.

I wanted to confirm how you would draw the correct structure for the following compound after undergoing a "water loss" in a mass spectrometer collision cell.

The molecule InChi is:
InChI=1S/C14H21NO2/c1-17-13-7-4-6-11(9-13)14(16)8-3-2-5-12(14)10-15/h4,6-7,9,12,16H,2-3,5,8,10,15H2,1H3/t12-,14-/m0/s1

Thanks for your help.




Online sjb

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Re: Question on correct chemical structure
« Reply #1 on: June 17, 2020, 07:58:04 AM »
CN(C)C[C@@H]1CCCC[C@@]1(C2=CC(=CC=C2)OC)O (racemic, I think)

What are your thoughts. How can you eliminate water?

Offline LightningShotz

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Re: Question on correct chemical structure
« Reply #2 on: June 17, 2020, 08:14:22 AM »
I came up with this but wasn't sure.

Online sjb

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Re: Question on correct chemical structure
« Reply #3 on: June 17, 2020, 09:13:04 AM »
Seems sensible but check the nitrogen and the conformation
« Last Edit: June 17, 2020, 10:36:07 AM by sjb »

Offline Babcock_Hall

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Re: Question on correct chemical structure
« Reply #4 on: June 17, 2020, 09:35:33 AM »
When -OH is lost from one carbon, what else is lost, and where is it lost?

Offline LightningShotz

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Re: Question on correct chemical structure
« Reply #5 on: June 17, 2020, 03:39:20 PM »
Seems sensible but check the nitrogen and the conformation
I’m not sure what you mean here?

Offline Babcock_Hall

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Re: Question on correct chemical structure
« Reply #6 on: June 18, 2020, 09:23:04 AM »
Look at the groups on nitrogen.

Offline LightningShotz

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Re: Question on correct chemical structure
« Reply #7 on: June 18, 2020, 03:34:42 PM »
Look at the groups on nitrogen.

I believe from the original InChi that it’s NH2.

Offline Babcock_Hall

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Re: Question on correct chemical structure
« Reply #8 on: June 18, 2020, 05:23:07 PM »
Look at the groups on nitrogen.

I believe from the original InChi that it’s NH2.
The drawing in the second post (by sjb) showed two methyl groups.  Also, you have not addressed my comment.

Online sjb

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Re: Question on correct chemical structure
« Reply #9 on: June 19, 2020, 03:04:06 AM »
I confess, I'm not sure if my translation of the InChi is correct. Looking at it again, it is probably the primary amine and a pure enantiomer (http://www.chemspider.com/Chemical-Structure.23976885.html)

Online sjb

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Re: Question on correct chemical structure
« Reply #10 on: June 22, 2020, 11:55:45 AM »
What is the mechanism of the dehydration?

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