I am looking at the difference between primary, secondary, and tertiary amines.

Image showing various simple organic functional group

What about if the nitrogen is double bonded to a carbon?

The mine functional group

Is this carbon counted twice, and is the molecule above a considered tertiary amine?

  • 5
    $\begingroup$ Imines can never be amines. Amines are amines. Imines are imines. Can an alkene be an alkane? $\endgroup$ Aug 6 '17 at 2:34
  • $\begingroup$ Imine is to amine as carbonyl is to ether. Do you think a carbonyl is an ether? $\endgroup$
    – Zhe
    Aug 7 '17 at 19:29
  • $\begingroup$ Also, the abbreviation using a degree sign is not common in chemistry. $\endgroup$
    – Jan
    Sep 7 '17 at 8:15

No. Imines cannot be considered an example of secondary amines any more than pyridine can be considered a tertiary amine.

The easiest way to think about this is with oxidation state: imines are at a higher oxidation level than amines, just as aldehydes are at a higher oxidation level than alcohols.

Aside from this 'intuitive' explanation, the IUPAC gold book (a source of chemical nomenclature) defines both amines and imines, clearly differentiating the two:

amines. Compounds formally derived from ammonia by replacing one, two or three hydrogen atoms by hydrocarbyl groups, and having the general structures $\ce{RNH2}$ (primary amines), $\ce{R2NH}$ (secondary amines), $\ce{R3N}$ (tertiary amines).

imines. Compounds having the structure $\ce{RN=CR2}$ (R = H, hydrocarbyl). Thus analogues of aldehydes or ketones, having NR doubly bonded to carbon; aldimines have the structure RCH=NR, ketimines have the structure $\ce{R'2C=NR}$ (R' ≠ H). Imines include azomethines and Schiff bases. Imine is used as a suffix in systematic nomenclature to denote the C=NH group excluding the carbon atom.


Generally NO. Tertiary amine is an ammonia derivative with 3 hydrogen atoms substituted to 3 alkyl/aryl substituents. Whereas imines exhibit some properties of tertiary amines (like pyridine). It can be protonated or alkylated and form iminium salts.

  • 2
    $\begingroup$ Pyridine is not a tertiary anime... $\endgroup$
    – Zhe
    Aug 7 '17 at 19:30

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