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Is an imine considered a secondary amine?
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Minhsan Nguyen
Is an imine considered a secondary amine?
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.
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.
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.
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:
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:
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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.
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.
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