Solvent effects on infrared frequencies—I. The complexing of acetone and cyclohexanone with p-cresol and other phenols

作者: K.B. Whetsel , R.E. Kagarise

DOI: 10.1016/S0371-1951(62)80140-4

关键词: PhotochemistryChemistrySolvent effectsCyclohexanonep-CresolAcetoneCyclohexaneStability constants of complexesEthanolPhenols

摘要: Abstract The carbonyl stretching bands of acetone and cyclohexanone were studied in various mixtures p-cresol cyclohexane. results indicate that 1:1 1:2 ketone-p-cresol complexes are formed at concentrations less than 0·3 M even higher exist concentrations. Formation constants for the determined used to resolve observed into spectra individual complexes. More limited data obtained with other phenols ethanol also presented. emphasize effects specific interactions on frequencies these systems. They show complex nature solvent-induced frequency shifts illustrate advantages using mixed solvents study shifts.

参考文章(35)
R. E. Kagarise, Infrared Intensity of the C–H Stretching Band of Chloroform in Some Halogenated Acetones The Journal of Chemical Physics. ,vol. 27, pp. 827- 828 ,(1957) , 10.1063/1.1743857
K.B. Whetsel, R.E. Kagarise, Solvent effects on infrared frequencies—II. The effects of chloroform and carbon tetrachloride on the carbonyl bands of ketones Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. ,vol. 18, pp. 329- 339 ,(1962) , 10.1016/S0371-1951(62)80141-6
Aubrey L McClellan, George C. Pimentel, Roger Hayward, The hydrogen bond ,(1960)
R.E. Kagarise, K.B. Whetsel, Solvent effects on infrared frequencies—III: The carbony bands of ethyl acetate, ethyl trichloroacetate and ethyl trifluoroacetate Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. ,vol. 18, pp. 341- 352 ,(1962) , 10.1016/S0371-1951(62)80142-8
Mitsuo Ito, Kōzō Inuzuka, Sunao Imanishi, Correlation between Solvent‐Induced Frequency Shifts of the n—π* Ultraviolet Absorption and the Infrared C=O Band of Ketones The Journal of Chemical Physics. ,vol. 31, pp. 1694- 1694 ,(1959) , 10.1063/1.1730692
Marie‐Louise Josien, Nelson Fuson, A New Analysis of the Effect of Polar Solvents Uponv(NH) of Pyrrole The Journal of Chemical Physics. ,vol. 22, pp. 1264- 1265 ,(1954) , 10.1063/1.1740360
L. J. Bellamy, H. E. Hallam, Infra-red spectra and solvent effects. Part 3.—Intermolecular and intramolecular hydrogen bonds Trans. Faraday Soc.. ,vol. 55, pp. 220- 224 ,(1959) , 10.1039/TF9595500220
Marie‐Louise Josien, Nelson Fuson, Infrared Study of the Effect of Solvent upon ν(NH) in Pyrrole The Journal of Chemical Physics. ,vol. 22, pp. 1169- 1177 ,(1954) , 10.1063/1.1740325
San-Ichibo Mizushima, Masamichi Tsuboi, Takehiko Shimanouchi, Yoshizo Tsuda, Spectroscopic investigation of the strength of hydrogen bonds formed by amides Spectrochimica Acta. ,vol. 7, pp. 100- 107 ,(1955) , 10.1016/0371-1951(55)80012-4
R. C. Lord, B. Nolin, H. D. Stidham, Quantitative Study of the Bonding of Chloroform-d in Various Solvents by Infrared Spectrometry1 Journal of the American Chemical Society. ,vol. 77, pp. 1365- 1368 ,(1955) , 10.1021/JA01610A088