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ERIC Number: EJ1062300
Record Type: Journal
Publication Date: 2015-Apr
Pages: 4
Abstractor: As Provided
Reference Count: 36
ISSN: ISSN-0021-9584
Proper Resonance Depiction of Acylium Cation: A High-Level and Student Computational Investigation
Esselman, Brian J.; Hill, Nicholas J.
Journal of Chemical Education, v92 n4 p660-663 Apr 2015
The 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.
Division 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:; Web site:
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: National Science Foundation
Authoring Institution: N/A
IES Grant or Contract Numbers: CHE-0840494