Editing Conjugated system (section)

== Stabilization energy ==
The quantitative estimation of stabilization from conjugation is notoriously contentious and depends on the implicit assumptions that are made when comparing reference systems or reactions. The energy of stabilization is known as the '''resonance energy''' when formally defined as the difference in energy between the real chemical species and the hypothetical species featuring localized π bonding that corresponds to the most stable [[Resonance (chemistry)|resonance form]].<ref>{{GoldBookRef |title=resonance energy |file=R05333 |accessdate=2019-01-06}}</ref> This energy cannot be measured, and a precise definition accepted by most chemists will probably remain elusive. Nevertheless, some broad statements can be made. In general, stabilization is more significant for cationic systems than neutral ones. For [[Butadiene|buta-1,3-diene]], a crude measure of stabilization is the [[activation energy]] for rotation of the C2-C3 bond. This places the resonance stabilization at around 6 kcal/mol.<ref>{{Cite journal|title=High Level ab Initio Energies and Structures for the Rotamers of 1,3-Butadiene|journal = The Journal of Physical Chemistry A|volume = 113|issue = 8|pages = 1601–1607|last1=Feller|first1=David|last2=Craig|first2=Norman C.|date=2009-02-05|language=EN|doi=10.1021/jp8095709|pmid = 19199679| bibcode=2009JPCA..113.1601F }}</ref> Comparison of heats of hydrogenation of [[Pentadiene|1,4-pentadiene]] and 1,3-pentadiene estimates a slightly more modest value of 3.5 kcal/mol.<ref>{{Cite book|title=Organic chemistry|last1=Carey|first1=Francis A.|last2=Guiliano|first2=Robert M.|date=2013-01-07|isbn=9780073402741|edition=Ninth|location=New York, NY|oclc=822971422}}</ref> For comparison, allyl cation has a gas-phase rotation barrier of around 38 kcal/mol,<ref>{{Cite journal|last1=Gobbi|first1=Alberto|last2=Frenking|first2=Gernot|date=1994-10-01|title=Resonance Stabilization in Allyl Cation, Radical, and Anion|journal=Journal of the American Chemical Society|volume=116|issue=20|pages=9275–9286|doi=10.1021/ja00099a052|bibcode=1994JAChS.116.9275G |issn=0002-7863}}</ref> a much greater penalty for loss of conjugation. Comparison of hydride ion affinities of propyl cation and allyl cation, corrected for inductive effects, results in a considerably lower estimate of the resonance energy at 20–22 kcal/mol.<ref>{{Cite journal|last1=Barbour|first1=Josiah B.|last2=Karty|first2=Joel M.|date=2004-01-14|title=Resonance Energies of the Allyl Cation and Allyl Anion: Contribution by Resonance and Inductive Effects toward the Acidity and Hydride Abstraction Enthalpy of Propene|journal=The Journal of Organic Chemistry|language=en|volume=69|issue=3|pages=648–654|doi=10.1021/jo035189m|pmid=14750787}}</ref> Nevertheless, it is clear that conjugation stabilizes allyl cation to a much greater extent than buta-1,3-diene. In contrast to the usually minor effect of neutral conjugation, aromatic stabilization can be considerable. Estimates for the resonance energy of benzene range from around 36–73 kcal/mol.<ref>{{Cite book|title=Chemical applications of group theory|last=Cotton|first=Frank Albert|date=1990|publisher=Wiley|isbn=978-0471510949|edition=3rd|location=New York|oclc=19975337|url-access=registration|url=https://archive.org/details/isbn_9780471510949}}</ref>