DOI: 10.1002/recl.19690880109. Electronic and steric effects in the hydrogenation of alkyl aryl ketones on palladium

Electronic and steric effects in the hydrogenation of alkyl aryl ketones on palladium

10.1002/recl.19690880109

Crossref journal-article

Wiley

Recueil des Travaux Chimiques des Pays-Bas (311)

Abstract

AbstractThe hydrogenation of some forty aromatic ketones to the corresponding alcohols has been studied in ethanol using carbon‐supported palladium as the catalyst. Zero order kinetics with respect to ketone is observed. For acetophenones electronic substituent effects may be expressed in terms of a Hammett‐Yukawa relationship with ρ = 0.7. 2‐Alkylacetophenones react very slowly. With alkyl phenyl ketones increase of size of the alkyl group causes increasing rate of hydrogenation. The adsorbed state is discussed on the basis of competition experiments.

Bibliography

van Bekkum, H., Kieboom, A. P. G., & van De Putte, K. J. G. (1969). Electronic and steric effects in the hydrogenation of alkyl aryl ketones on palladium. Recueil Des Travaux Chimiques Des Pays-Bas, 88(1), 52â61. Portico.

Authors 3

H. van Bekkum (first)
A.P.G. Kieboom (additional)
K.J.G. van De Putte (additional)

References 27 Referenced 29

{'key': 'e_1_2_1_1_2', 'first-page': '458', 'author': 'Jardine I.', 'journal-title': 'J. Chem. Soc.'} / J. Chem. Soc. by Jardine I.
10.1021/ja01525a001
10.1007/BF02154560
{'key': 'e_1_2_1_4_2', 'first-page': '370', 'volume': '3', 'author': 'Hernandez L.', 'year': '1948', 'journal-title': 'J. Colloid Sci.'} / J. Colloid Sci. by Hernandez L. (1948)
10.1021/ja01100a040
{'key': 'e_1_2_1_6_2', 'first-page': '310', 'volume': '4', 'author': 'Finkelstein A.V.', 'year': '1967', 'journal-title': 'Reactionnaya Sposobnost Organ. Soedin.'} / Reactionnaya Sposobnost Organ. Soedin. by Finkelstein A.V. (1967)
{'key': 'e_1_2_1_6_3', 'first-page': '605', 'volume': '4', 'author': 'Finkelstein A.V.', 'year': '1967', 'journal-title': 'Reactionnaya Sposobnost Organ. Soedin.'} / Reactionnaya Sposobnost Organ. Soedin. by Finkelstein A.V. (1967)
{'key': 'e_1_2_1_7_2', 'first-page': '205', 'volume': '605', 'author': 'Kindler K.', 'year': '1957', 'journal-title': 'Ann.'} / Ann. by Kindler K. (1957)
{'key': 'e_1_2_1_8_2', 'volume-title': 'Catalysis', 'author': 'Corson B.B.', 'year': '1955'} / Catalysis by Corson B.B. (1955)
10.1021/ja01165a091
{'key': 'e_1_2_1_10_2', 'first-page': '388', 'volume-title': 'Hydrogenation in Solutions', 'author': "Sokol'skii D.V.", 'year': '1964'} / Hydrogenation in Solutions by Sokol'skii D.V. (1964)
H.A.SmithandC.P.Rader Proc. Intern. Congr. on Catalysis 2nd Paris 19601 1213(1961).
G.C.Bond Chem. Ind. London1967 2018.
H.A.SmithandW.E.Campbell Proc. Intern. Congr. on Catalysis 3rd Amsterdam 19642 1383(1965).
{'key': 'e_1_2_1_14_2', 'volume-title': 'Physical Organic Chemistry', 'author': 'Hammett L.P.', 'year': '1940'} / Physical Organic Chemistry by Hammett L.P. (1940)
10.1002/recl.19590781009
10.1246/bcsj.39.2274
Computer calculations showed optimal correlation in case of a resonance parameter 1.6 (correlation coefficient 0.97). However this value is considered to be much too high for the present reaction. Failure will be due to the fact that beside electronic effects other effects are operative (see text).
10.1016/S0360-0564(08)60685-9
{'key': 'e_1_2_1_19_2', 'first-page': '4879', 'volume': '82', 'author': 'Hine J.', 'year': '1960', 'journal-title': 'J. Am. Chem. Soc.'} / J. Am. Chem. Soc. by Hine J. (1960)
It may be noted that the kinetics observed excludes the possibility that enolization is rate determining. Accordingly pivalophenone and acetophenone showed practically the same ratio of hydrogenation rates when using ethanol with or without alkali.
10.1016/0021-9517(67)90052-8
10.1021/ja01111a040
10.1016/S0040-4039(00)90810-4
10.1002/recl.19680870705
10.1021/ja00862a012
10.1002/bscb.19500590905

Dates

Type	When
Created	14 years, 11 months ago (Sept. 14, 2010, 12:19 a.m.)
Deposited	1 year, 9 months ago (Nov. 13, 2023, 2:54 p.m.)
Indexed	1 year, 1 month ago (July 24, 2024, 4:35 a.m.)
Issued	56 years, 7 months ago (Jan. 1, 1969)
Published	56 years, 7 months ago (Jan. 1, 1969)
Published Online	14 years, 11 months ago (Sept. 2, 2010)
Published Print	56 years, 7 months ago (Jan. 1, 1969)

Funders 0

None

BibTeX

@article{van_Bekkum_1969, title={Electronic and steric effects in the hydrogenation of alkyl aryl ketones on palladium}, volume={88}, ISSN={0165-0513}, url={http://dx.doi.org/10.1002/recl.19690880109}, DOI={10.1002/recl.19690880109}, number={1}, journal={Recueil des Travaux Chimiques des Pays-Bas}, publisher={Wiley}, author={van Bekkum, H. and Kieboom, A.P.G. and van De Putte, K.J.G.}, year={1969}, month=jan, pages={52–61} }

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