Los nitrilos conocidos también como cianuros, son compuestos orgánicos que poseen un grupo funcional el cual está formado por un enlace triple carbono-nitrógeno; y además son considerados como derivados del cianuro de hidrógeno (H-C≡N, aunque también se puede escribir como simplemente HCN), donde el hidrógeno es sustituido por un grupo alquilo o arilo, según corresponda.
Los cianuros o nitrilos se pueden clasificar como aromáticos y alifáticos, donde Ar es un grupo aril (Ar-C≡N) y R un grupo alquil (R-C≡N). Por ejemplo:
C6H5-C≡N es un nitrilo aromático ya que posee un benceno en su estructura, por lo tanto su nombre es benzonitrilo o bencenocarbonitrilo.
CH3-C≡N es un nitrilo alifático, ya que está formado por un metil en su estructura, entonces su nombre seria etanonitrilo.
NOMENCLATURA PARA LOS NITRILOS
Los nitrilos se pueden nombrar utilizando los siguientes sistemas:
- Nomenclatura IUPAC o Sustitutiva: Añadir el sufijo -nitrilo al nombre del hidrocarburo de acuerdo a la cantidad de carbonos que presente el compuesto. Por ejemplo: alcanonitrilo.
- Nomenclatura Radicofuncional: Se le nombra considerándolo como un derivado del cianuro de hidrógeno. Por ejemplo: cianuro de alquilo/arilo.
- Nomenclatura Común o Trivial: Nombrar como derivado del ácido carboxílico correspondiente. Por ejemplo: Carboxinitrilo.
- Cuando los nitrilos se encuentran formando parte de una cadena carbonada, pero como sustituyente (-C≡N) se les llama ciano. Los nitrilos tienen prioridad sobre los siguientes grupos funcionales: aldehídos, cetonas, alcoholes, mercaptanos, aminas, éteres, sulfuros, alquenos, alquinos, halogenuros, nitro y alcanos.
- Cuando los nitrilos presentan un ciclo en su fórmula se le debe colocar la terminación -carbonitrilo.
- Para los dinitrilos, se emplea las nomenclaturas IUPAC y común. Para la IUPAC se sigue la siguiente fórmula: alcanodinitrilo. Para la nomenclatura común se emplea la siguiente fórmula: dicarboxilonitrilo.
EJERCICIOS
IUPAC: Hexanonitrilo
Radicofuncional: cianuro de hexilo
Común: Capronitrilo
IUPAC: Butanodinitrilo
Común: Succinonitrilo
IUPAC: ácido-5-ciano-3-cloro-hexanoico
Común: ácido-5-ciano-3-cloro-caproico
IUPAC: 3-oxociclohexanocarbonitrilo
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