This paper reports on an experimental study of the C=O stretching vibration frequency in a large number of quinonoid compounds, both substituted and unsubstituted. For nonsubstituted ortho and para quinones, relationships between the carbonyl frequency and (a) the number of fused rings, (b) the oxidation‐reduction potential, and (c) the index of free valence on the parent hydrocarbon are pointed out and discussed. It is shown that for a six‐atom quinonoid ring the C=O frequency is, to a first approximation, a function of the C=O bond order. For substituted quinones, the variation in the carbonyl frequency is related to the induction effect of the substituent in the same way as is the variation in oxidation‐reduction potential. Certain hydroxy‐substituted quinones show spectral anomalies which do not seem to fit into the usual category of hydrogen bonded compounds.
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February 1953
Research Article|
February 01 1953
An Infrared Spectroscopic Study of the Carbonyl Stretching Frequency in a Group of Ortho and Para Quinones
Marie‐Louise Josien;
Marie‐Louise Josien
Fisk University, Nashville, Tennessee
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Nelson Fuson;
Nelson Fuson
Fisk University, Nashville, Tennessee
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Jeanne‐Marie Lebas;
Jeanne‐Marie Lebas
Fisk University, Nashville, Tennessee
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Thomas M. Gregory
Thomas M. Gregory
Fisk University, Nashville, Tennessee
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J. Chem. Phys. 21, 331–340 (1953)
Article history
Received:
July 16 1952
Citation
Marie‐Louise Josien, Nelson Fuson, Jeanne‐Marie Lebas, Thomas M. Gregory; An Infrared Spectroscopic Study of the Carbonyl Stretching Frequency in a Group of Ortho and Para Quinones. J. Chem. Phys. 1 February 1953; 21 (2): 331–340. https://doi.org/10.1063/1.1698881
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