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mesomeric(resonance effect)

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mesomeric(resonance effect)

Post  thedy on Tue Jun 21, 2011 12:10 pm

Why CN and COOH and NO2 groups have negativ mesomeric effect.I have read organic books,but I have found only CN and COOH and NO2 groups have negativ mesomeric effect,but there wasn t explained,why it is so.I know that negativ mesomeric effect have only these groups,which have double bond,but why?And positiv mesomeric effect have only these groups,which have lone electron pair,but again,WHY?In book it was explained too,that for example in nitrobenzene NO2 group attract electrons,and benzene needs balance electron deficit,and that is why lone electron pair goes from N to benzene,but this explanation is not enough for me.How is possible,that lone electron pair goes to benzene.
And here goes my next question.In chlorbenzene chlor causes positiv mesomeric effect,because chlor has lone electron pair.But in for example chloroform chlor causes negative inductive effect,it means,that in chloroform Chlor takes electrons,but in chlorbenzene Chlor gives electrons,WHY?
Thanks for patient


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