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Slebocka-Tilk, H., Bennet, A. J., Keillor, J. W., Brown, R. S., Guthrie, J. Peter, Jodhan, A. (1990) Oxygen-18 exchange accompanying the basic hydrolysis of primary, secondary, and tertiary toluamides. 2. The importance of amine leaving abilities from the anionic tetrahedral intermediate. Journal Of The American Chemical Society, 112 (23) 8507-8514 doi:10.1021/ja00179a040

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Reference TypeJournal (article/letter/editorial)
TitleOxygen-18 exchange accompanying the basic hydrolysis of primary, secondary, and tertiary toluamides. 2. The importance of amine leaving abilities from the anionic tetrahedral intermediate
JournalJournal Of The American Chemical Society
AuthorsSlebocka-Tilk, H.Author
Bennet, A. J.Author
Keillor, J. W.Author
Brown, R. S.Author
Guthrie, J. PeterAuthor
Jodhan, A.Author
Year1990 (November)Volume112
Issue23
PublisherAmerican Chemical Society (ACS)
DOIdoi:10.1021/ja00179a040Search in ResearchGate
Generate Citation Formats
Mindat Ref. ID1444660Long-form Identifiermindat:1:5:1444660:1
GUID0
Full ReferenceSlebocka-Tilk, H., Bennet, A. J., Keillor, J. W., Brown, R. S., Guthrie, J. Peter, Jodhan, A. (1990) Oxygen-18 exchange accompanying the basic hydrolysis of primary, secondary, and tertiary toluamides. 2. The importance of amine leaving abilities from the anionic tetrahedral intermediate. Journal Of The American Chemical Society, 112 (23) 8507-8514 doi:10.1021/ja00179a040
Plain TextSlebocka-Tilk, H., Bennet, A. J., Keillor, J. W., Brown, R. S., Guthrie, J. Peter, Jodhan, A. (1990) Oxygen-18 exchange accompanying the basic hydrolysis of primary, secondary, and tertiary toluamides. 2. The importance of amine leaving abilities from the anionic tetrahedral intermediate. Journal Of The American Chemical Society, 112 (23) 8507-8514 doi:10.1021/ja00179a040
In(1990, November) Journal Of The American Chemical Society Vol. 112 (23) American Chemical Society (ACS)

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Bennet, A. J., Slebocka-Tilk, H., Brown, R. S., Guthrie, J. Peter, Jodhan, A. (1990) Concurrent oxygen-18 exchange accompanying the acid-catalyzed hydrolysis of anilides. Implications for the lifetimes of reversibly formed intermediates. Journal Of The American Chemical Society, 112 (23) 8497-8506 doi:10.1021/ja00179a039
Slebocka-Tilk, H., Bennet, A. J., Hogg, Heather J., Brown, R. S. (1991) Predominant oxygen-18 exchange accompanying the base hydrolysis of a tertiary toluamide: N-ethyl-N-(trifluoroethyl)toluamide. Assessment of the factors that influence partitioning of anionic tetrahedral intermediates. Journal Of The American Chemical Society, 113 (4) 1288-1294 doi:10.1021/ja00004a032
Brown, R. S., Bennet, A. J., Slebocka-Tilk, H., Jodhan, A. (1992) Base-catalyzed hydrolysis and carbonyl-18O exchange kinetics for toluamides containing amine portions of reduced basicity. N-Toluoyl-3,3,4,4-tetrafluoropyrrolidine and N-toluoylpyrrole. Journal Of The American Chemical Society, 114 (8) 3092-3098 doi:10.1021/ja00034a051
Bennet, A. J., Slebocka-Tilk, H., Brown, R. S. (1992) Observation of large amounts of carbonyl-18O exchange concurrent with acid-catalyzed hydrolysis of toluamides having amine portions of reduced basicity. The involvement of protonated intermediates in the acid-catalyzed hydrolysis of N-toluoylpyrrole. Journal Of The American Chemical Society, 114 (8) 3088-3092 doi:10.1021/ja00034a050
Slebocka-Tilk, H., Rescorla, Christopher G., Shirin, Salma, Bennet, Andrew J., Brown, R. S. (1997) Water Catalyzed Hydrolysis ofp-Nitrotrifluoroacetanilide and Trifluoroacetanilide. Carbonyl18O-Exchange Does Not Accompany the Water Reaction. Journal Of The American Chemical Society, 119 (45) 10969-10975 doi:10.1021/ja971463g
Slebocka-Tilk, H., Brown, R. S., Olekszyk, J. (1987) Reversible formation of intermediates during hydronium-catalyzed hydrolysis of amides. Observation of substantial oxygen-18 exchange in the hydrolysis of acetanilide and N-cyclohexylacetamide. Journal Of The American Chemical Society, 109 (15) 4620-4622 doi:10.1021/ja00249a027
Bennet, A. J., Wang, Qing Ping, Slebocka-Tilk, H., Somayaji, V., Brown, R. S., Santarsiero, B. D. (1990) Relationship between amidic distortion and ease of hydrolysis in base. If amidic resonance does not exist, then what accounts for the accelerated hydrolysis of distorted amides?. Journal Of The American Chemical Society, 112 (17) 6383-6385 doi:10.1021/ja00173a029
Brown, R. S., Slebocka-Tilk, H., Bennet, A. J., Bellucci, G., Bianchini, R., Ambrosetti, R. (1990) Investigation of the early stages of electrophilic addition of bromine to olefins. Kinetic evidence for a reversibly formed bromonium ion in the reaction of bromine with tetraisobutylethylene. Journal Of The American Chemical Society, 112 (17) 6310-6316 doi:10.1021/ja00173a019
Brown, R. S., Slebocka-Tilk, H., Buschek, J. M., Ulan, J. G. (1984) Hydrolyses of 2-(trimethylsilyl) N1-heterocycles. Involvement of zwitterions in the hydrolysis of 2-(trimethylsilyl)-N-methylimidazole, 2-(trimethylsilyl)pyridine, and 2-[(trimethylsilyl)methyl]-N-methylimidazole. Journal Of The American Chemical Society, 106 (20) 5979-5984 doi:10.1021/ja00332a038
Nagorski, R. W., Slebocka-Tilk, H., Brown, R. S. (1994) Observation of an unusually large inverse secondary deuterium kinetic isotope effect for the reaction of a sterically congested olefin with bromine. Journal Of The American Chemical Society, 116 (1) 419-420 doi:10.1021/ja00080a067
Yaggi, N. F., Douglas, K. T. (1977) A ketene intermediate in S-acetoacetyl coenzyme A hydrolysis. Direct comparison of relative leaving abilities of anionic oxygen and sulfur(II) groups from an acyl center. Journal Of The American Chemical Society, 99 (14) 4844-4845 doi:10.1021/ja00456a061
 
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