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Autor/inn/enEsselman, Brian J.; Hill, Nicholas J.
TitelProper Resonance Depiction of Acylium Cation: A High-Level and Student Computational Investigation
QuelleIn: Journal of Chemical Education, 92 (2015) 4, S.660-663 (4 Seiten)Infoseite zur Zeitschrift
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Spracheenglisch
Dokumenttypgedruckt; online; Zeitschriftenaufsatz
ISSN0021-9584
DOI10.1021/ed5002152
SchlagwörterInvestigations; Undergraduate Students; Molecular Structure; Knowledge Representation; Science Education; Organic Chemistry; Misconceptions; Curriculum Implementation; Teaching Methods; Educational Practices; Science Experiments; Science Activities
AbstractThe electronic and molecular structure of the acylium cation ([CH[subscript 3]CO][superscript +], 1) receives varied treatment in undergraduate textbooks and online resources. The overall structure of 1 is typically represented as an equal combination of resonance structures containing C-O triple and double bonds, the latter structure occasionally being shown with a bent C-C-O bond angle. This description is inconsistent with available experimental and theoretical data, all of which indicate that 1 is a linear molecule containing a C[triple bar]O bond, and can lead students to a false conception of structure, conjugation, and charge distribution. A set of simple computational exercises is reported that allows students to calculate and rationalize the most accurate resonance representation of 1. (As Provided).
AnmerkungenDivision of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Erfasst vonERIC (Education Resources Information Center), Washington, DC
Update2020/1/01
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