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If It's Resonance, What Is Resonating?
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Abstract
The resonance terminology that accompanies use of more than one Lewis-type structure to describe delocalized bonding in molecules has been leading students astray for more than half a century. In this article I review the origin of the terminology and how the original usage has evolved to reduce confusion. I furthermore suggest that substitution of more easily understood terms that lack the gratuitous implications of the word resonance could finally eliminate the confusion.
Keywords (Audience):
First-Year Undergraduate / GeneralKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Textbooks / Reference BooksKeywords (Subject):
Aromatic CompoundsCiting Articles
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This article has been cited by 6 ACS Journal articles (5 most recent appear below).
Assessment of Organic Chemistry Students’ Knowledge of Resonance-Related Structures
Rosa Betancourt-Pérez and Luis Javier Olivera, Julio E. RodríguezJournal of Chemical Education2010 87 (5), 547-551Assessment of Organic Chemistry Students’ Knowledge of Resonance-Related Structures
Rosa Betancourt-Pérez and Luis Javier Olivera, Julio E. RodríguezJournal of Chemical Education2010 87 (5), 547-551This study examines how well second-year nonmajor organic chemistry students are learning to draw, interpret, and understand resonance-related structures. Students were tested seven times throughout an academic year using a set of four tasks that ...
Ionization of Amino-, Thio- and Hydroxy-naphtalenes via Free (Unhindered) Electron Transfer
Aliaksandr Baidak, Sergej Naumov, Ralf Hermann and Ortwin BredeThe Journal of Physical Chemistry A2008 112 (44), 11036-11043Ionization of Amino-, Thio- and Hydroxy-naphtalenes via Free (Unhindered) Electron Transfer
Aliaksandr Baidak, Sergej Naumov, Ralf Hermann and Ortwin BredeThe Journal of Physical Chemistry A2008 112 (44), 11036-11043The electron transfer from various monosubstituted naphthyl derivatives (naphtols, NpOH; naphtylamines, NpNH2; and thionaphtols, NpSH) to parent n-BuCl radical cations was studied by means of pulse radiolysis. The experiments reveal the synchronous and ...
"As Simple as Possible, but Not Simpler"—The Case of Dehydroascorbic Acid
Robert C. KerberJournal of Chemical Education2008 85 (9), 1237"As Simple as Possible, but Not Simpler"—The Case of Dehydroascorbic Acid
Robert C. KerberJournal of Chemical Education2008 85 (9), 1237Ascorbic acid (vitamin C) is an essential nutrient, whose metabolic roles depend on its function as a reducing agent. Textbooks routinely assign its oxidized form, dehydroascorbic acid, a tricarbonyl structure that is highly improbable in aqueous solution ...
The Concept of Resonance
Donald G. TruhlarJournal of Chemical Education2007 84 (5), 781The Concept of Resonance
Donald G. TruhlarJournal of Chemical Education2007 84 (5), 781This article begins by responding to a recent suggestion that "resonance", as in valence bond theory, should be relabeled "delocalization". It is shown that these are different concepts, and the meaning of resonance in modern valence bond theory is ...
More on the Nature of Resonance
William B. JensenJournal of Chemical Education2006 83 (9), 1290More on the Nature of Resonance
William B. JensenJournal of Chemical Education2006 83 (9), 1290Supplements a recent article on the interpretation of resonance theory with three additional observations—one historical and two conceptual.
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- Received: August 03, 2009
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