La resonancia, también llamada mesomería o efecto mesómero, es un mecanismo que permite simbolizar moléculas orgánicas mediante la combinación lineal de estructuras teóricas de dicha molécula, que no corresponden con la estructura real pero que permite conocer lo más preciso posible, la constitución real de ella. La resonancia se representan con la letra R o la letra M y no es más que el movimiento de electrones en una cadena carbonada. Para que esta se pueda dar, debe estar presentes carbonos con hibridación sp y sp².
Es importante tener en cuenta que mientras más resonante sea la molécula, menos reactivo es y viceversa.
El efecto resonante o mesómero negativo es aquel que se genera cuando el sustituyente es un grupo que atrae electrones. Por ejemplo: propenal.
El oxígeno atrae hacia él un par de electrones del doble enlace (C=O), quedando este cargado negativamente. Por su parte, el doble enlace del propenal retribuye la pérdida de electrones del carbono.
Otros sustituyentes que producen un efecto mesomérico negativo: nitro, nitrilo, acetilo, etc.
Este se manifiesta cuando el sustituyente es un grupo que dona electrones. Por ejemplo: bromoeteno.
El bromo es un sustituyente que dona electrones, por lo tanto este cede un par al carbono generándose un enlace doble.
Otros sustituyentes que producen un efecto mesomérico positivo: alcoholes, aminas, éteres, halogenos, entre otros.
El concepto de resonancia fue propuesto por el científico estadounidense Linus Pauling en el año 1928, mientras que la palabra mesomería fue establecida por el científico británico Christopher Kelk Ingold en el año 1938 como opción al concepto ya propuesto.
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