what is the product of reaction of Traut's reagent with aliphatic hydroxyl called? I am reacting Traut's reagent with Fmoc protected Doxorubicin and I just need to know the name of the product after Traut's regent reacts with the hydroxyl group. What is $\ce{OCNH2}$ called? I am looking for a name for $\ce{OCNH2}$ circled in red.

Sulfhydryl N-Fmoc Dox


The group itself unprotonated is called a carboximidate as noted by the Wiki page. The acid that the group is derived from is carboximidic acid. As is common practice with imines, the nomenclature for the corresponding protonated halide is done by removing -es, adding -ium, and the halide name. If this is done using the acid name, the group will be called a carboximinium chloride.

  • $\begingroup$ Maybe carboximiDium chloride? $\endgroup$ Apr 7 '20 at 19:17

There is a paper (1) on imino-ether salts with rather similar structure including $\ce{-C(NH2+)O\! -}$ group:

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This compound comes with two defined names, which OP can use as an example:

  1. Hydrogenethylpropylimidate tetrachloroaurate(III) (paper)
  2. 1-(Ethoxy)propylimidium tetrachloro-gold(III) (generated by CCDC)

Subjectively, carboximidate fits perfectly if the group wouldn't carry a positive charge; as long as this is the case, probably carboximidium would fit better.

(1) Potts, R. A.; Gaj, D. L.; Schneider, W. F.; Dean, N. S.; Kampf, J. W.; Oliver, J. P. Polyhedron 1991, 10 (14), 1631–1637. DOI: 10.1016/S0277-5387(00)83774-2


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