Questions tagged [resonance]

Resonance refers to the representation of the electronic structure of a molecular entity in terms of contributing structures. The tag should be applied to any question that concern resonance structures or resonance energy. This tag should not be applied to questions about aromatic compounds (use the [aromatic-compounds] tag instead)

Resonance as defined by in the IUPAC GoldBook:

In the context of chemistry, the term refers to the representation of the electronic structure of a molecular entity in terms of contributing structures. Resonance among contributing structures means that the wavefunction is represented by 'mixing' the wavefunctions of the contributing structures. The concept is the basis of the quantum mechanical valence bond methods. The resulting stabilization is linked to the quantum mechanical concept of 'resonance energy'. The term resonance is also used to refer to the delocalization phenomenon itself.

Mesomerism as defined in the IUPAC Gold Book:

Essentially synonymous with resonance. The term is particularly associated with the picture of π-electrons as less localized in an actual molecule than in a Lewis formula. The term is intended to imply that the correct representation of a structure is intermediate between two or more Lewis formulae.

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What are the correct resonance structures of nitrous oxide?

There was a question in one of my exam papers to draw the resonance structures for $\ce{N2O}$. These are the ones I drew, but they were not awarded marks: The ones in the marking scheme are as follows: Can anyone please explain why mine aren't…
lucy G
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Rationalizing the Planarity of Formamide

In formamide, the nitrogens appear to be $\ce{sp^3}$ hybridized, implying tetrahedral geometry. However, analysis shows that the molecule is actually very nearly planar with bond angles close to 120 degrees. EDIT: as suggested by Martin and another…
Dissenter
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Why is the original Pauling's theory of resonance that uses superposition of wavefunctions not used today?

I have recently studied superposition of states (also the famous Schrodinger's cat), measurement problem, decoherence & so on. I then read the resonance concept from Atkins' Physical Chemistry where it was written as: It is the superposition of…
user5764
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What is the most "important" resonance structure of SCN⁻?

Numerous online references say that $\ce{SCN-}$ has two resonance structures: I am wondering why this structure is not also possible? I expect structure 3 to be rare because of the high formal charges, but shouldn't it be included as a possible…
Anon
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Validity of ionic resonance structures

What's wrong with ionic resonance structures? I asked one professor about them once and all he commented was "I've seen them too, and I think they're wrong." Another professor rejected an ionic resonance structure showing the "H+" ion and asked me…
Dissenter
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Can atoms delocalize in molecules?

Electrons can delocalize over multiple equally probable bonding structures. Can atoms delocalize over multiple equally probably bonding structures in certain cases? It seems to me that any such effect would be most pronounced with very small atoms…
Molly Stewart-Gallus
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What is the meaning of "charge separation" in resonance?

I've read that the resonance structures in which there is lesser 'charge separation' contribute more to the resonance hybrid than the ones with greater charge separation. But I am unable to understand why it is so. I mean isn't it correct that the…
ShankRam
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Is resonance always stabilizing

Does resonance always stabilize a molecule or can resonance effects destabilize molecules? The only example I can think of in which resonance (more accurately, conjugation) destabilizes molecules is in the cases of anti-aromatic compounds. Is this…
Dissenter
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Which of the canonical structures contributes more to resonance hybrid?

I am quoting a rule on resonance from Organic Chemistry by T.W. Graham Solomons, Craig B. Fryhle, 12th edition, page 25. Structures in which all the atoms have a complete valence shell of electrons (i.e., the noble gas structure) are more…
Chakravarthy Kalyan
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Resonance hybrid of nitrosobenzene

In nitrosobenzene, there are two ways that the $\ce{-N=O}$ group can show mesomeric effect. It can show positive mesomeric effect by becoming $\ce{=N+=O}$ It can show negative mesomeric effect by becoming $\ce{=N-O-}$ So will the electron…
gauri agrawal
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Isotopes and electronegativity

Is there any difference between electronegativities of isotopes of the same element. For example consider the above compound. Will all the resonance structures be equivalent? Also if I place the above compound in water (which will act as a Bronsted…
gauri agrawal
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Stabilization by resonance

My textbook (NCERT Chemistry. Part I. Textbook for Class XI [1, p. 106]) states that Resonance stabilizes the molecule as the energy of the resonance hybrid is less than the energy of any single canonical structure by giving two examples:…
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Canonical structures of (1E)-prop-1-en-1-yl acetate

I have to find all of the possible canonical structures of this molecule And here's what I did Are they correct and if yes, did I miss any possibility?
p-bromonitrobenzene
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Is my reasoning for resonance structures correct?

given this picture, which resonance structure is correct? I'm thinking 1 and 3. You can't have 2 because the carbon which originally had a negative charge would be making 5 bonds, and you can't have 4 because the carbon on the right side of the new…
nachime
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Which one is the most stable canonical structure?And why?

According to my book the answer is given that structure III is the most stable because all the atoms have complete octets. But I think it should be II because of, (a) Structure III has positive charge on a highly electronegative atom and (b) In…
student
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