11
$\begingroup$

enter image description hereFormula

C13H8Cl3NO

SMILES

C1=C(C(=CC(=C1)Cl)Cl)N(C(C2=CC=CC=C2)=O)Cl

I found the diagram on the left in a book and drew the one on the right using

https://pubchem.ncbi.nlm.nih.gov/edit2/index.html

And got the SMILES description from that.

Any clues as to what might be an IUPAC name and the formal way to write it out? Have I have even drawn it correctly? I could not do it exactly because the two rings kept connecting if I followed the same orientation. I don't know enough about double ring compounds to even hazard a guess.

Is there a automatic naming engine out there?

A compound called British Impregnite found in The Scientific method by Louis F. Fieser p.137

Improve this question
$\endgroup$
4
  • 1
    $\begingroup$ Try Chemspider chemspider.com $\endgroup$
    – Waylander
    Commented Feb 27, 2019 at 19:28
  • 4
    $\begingroup$ Chemdoodle thinks it is [N-Chloro(2,4-dichlorophenyl)amino]phenylformaldehyde but there is probably a less systematic version as well. $\endgroup$
    – matt_black
    Commented Feb 27, 2019 at 19:36
  • 5
    $\begingroup$ @matt_black Wow, that's like most complicated, but very much not systematic name I've seen. $\endgroup$
    – Mithoron
    Commented Feb 27, 2019 at 19:51
  • 5
    $\begingroup$ @matt_black That's Chemdoodle being Chemdoodle, I think:) $\endgroup$
    – andselisk ♦
    Commented Feb 27, 2019 at 19:54

2 Answers 2

Reset to default
16
$\begingroup$

Well, let's reconstruct that starting from the very right side, where it says a $\ce{C_6H_5}$. The ring and the $\ce{CO}$ group would be a benzaldehyde if it had an $\ce{H}$ instead of an $\ce{N}$, right? Or a benzoic acid if it was $\ce{OH}$ instead of $\ce{N}$. So what would it be if it had an $\ce{NH_2}$-group? It would be a benzamide. If the $\ce{N}$ is substituted with for example a chloride we call that N-chlorobenzamide. And now we have another $\ce{N}$-centered ligand, the second phenyl ring. The ring has three positions, the one where it's connected to the rest of the molecule would be 1, so that makes a 2,4-dichlorophenyl.

Summarizing we get N-chloro-N-(2,4-dichlorophenyl)benzamide

Improve this answer
$\endgroup$
2
  • $\begingroup$ Thank you for the steps, it gives me great comfort to know it is no more complicated than Finnish grammar. To humour an inorganic chemistry fan like me how do you know to start with the right hand side? Is the fact that the one ring has a carbon attached the reason it is first? Could the substance be named by starting from the other ring? $\endgroup$
    – KalleMP
    Commented Feb 28, 2019 at 21:35
  • 1
    $\begingroup$ Intuition, the benzene ring + the carbonyl group directly reminded me of benzaldehyde. With an N-Cl attached it didn't become any harder as I showed above. From the other side I had to guess. A benzene ring with an N could be derived from Aniline, there are so called Benzanilides but the other way around it was much easier as it already had a name. $\endgroup$
    – Justanotherchemist
    Commented Mar 1, 2019 at 7:44
11
$\begingroup$

There is a paper [1] reporting a structural investigation of aromatic N-chloroamides. They investigated polymorphs of similar compound they refer to as N-chloro-N-phenylbenzamide:

enter image description here

Chlorinated product, I suspect, is indeed is going to be named N‐chloro‐N‐(2,4‐dichlorophenyl)benzamide, as the first answer suggested.

References

  1. Naumov, P.; Topcu, Y.; Eckert-Maksić, M.; Glasovac, Z.; Pavošević, F.; Kochunnoonny, M.; Hara, H. Photoinduced Rearrangement of Aromatic N-Chloroamides to Chloroaromatic Amides in the Solid State: Inverted $Π_\ce{N}–Σ_\ce{N}$ Occupational Stability of Amidyl Radicals. The Journal of Physical Chemistry A 2011, 115 (26), 7834–7848. https://doi.org/10.1021/jp203771c.
Improve this answer
$\endgroup$
2
  • $\begingroup$ Thank you for your research and input. I am not sure why there are two N's if they refer to the one nitrogen. How does one know what to do if there were two nitrogens? $\endgroup$
    – KalleMP
    Commented Mar 1, 2019 at 20:22
  • 1
    $\begingroup$ I'm glad I could help. Two N-'s reflect the fact there are two groups attached to the same nitrogen; if there were more than one nitrogen, prime(s) ' and superscripted numerical locants would be used to differentiate nitrogen atoms. $\endgroup$
    – andselisk ♦
    Commented Mar 2, 2019 at 4:28

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge you have read our privacy policy.

Not the answer you're looking for? Browse other questions tagged or ask your own question.