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The '''mesomeric effect''' or '''resonance effect''' in [[chemistry]] is a property of [[substituent]]s or [[functional group]]s in a [[chemical compound]]. The effect is used in a qualitative way and describes the electron withdrawing or releasing properties of substituents based on relevant [[resonance structure]]s and is symbolized by the letter '''M'''. The mesomeric effect is negative ('''-M''') when the substituent is an electron-withdrawing group and the effect is positive ('''+M''') when based on resonance the substituent is an electron releasing group.
*Examples of -M substituents: [[acetyl]] (UPAC ethanoyl) - [[nitrile]] - [[nitro]]
*Examples of +M substituents: [[alcohol]] - [[amine]]
The net electron flow from or to the substituent is determined also by the [[inductive effect]]. It's important to note that the mesomeric effect as a result of p - orbital overlap (resonance) has absolutely no effect on this inductive effect, as the inductive effect is purely to do with the [[electronegativity]] of the atoms and their structural chemistry (which atoms are connected to which).
The concepts of mesomeric effect, '''mesomerism''' and '''mesomer''' were introduced by [[Christopher Kelk Ingold|Ingold]] in 1938 as an alternative to the [[Linus Pauling|Pauling's]] synonymous concept of [[resonance effect|resonance]] <ref>''If It's Resonance, What Is Resonating?'' Kerber, Robert C. . J. Chem. Educ. '''2006''' 83 223. [http://www.jce.divched.org/Journal/Issues/2006/Feb/abs223.html Abstract]</ref>. Mesomerism is in this context is often encountered in German and French literature but in English literature the term resonance dominates.
== External links==
* IUPAC [[Gold Book]] [http://www.iupac.org/goldbook/M03844.pdf definition]
== See also ==
* [[List of publications in chemistry#Organic chemistry|Important publications in organic chemistry]]
== References ==
<references />
[[Category:Chemical bonding]]
[[de:Mesomerer Effekt]]
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