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dc.contributor.authorSzostak, Michal
dc.contributor.authorYao, Lei
dc.contributor.authorDay, Victor W.
dc.contributor.authorPowell, Douglas R.
dc.contributor.authorAubé, Jeffrey
dc.date.accessioned2017-06-06T16:37:45Z
dc.date.available2017-06-06T16:37:45Z
dc.date.issued2010-07-07
dc.identifier.citationSzostak, M., Yao, L., Day, V. W., Powell, D. R., & Aubé, J. (2010). Structural Characterization of N-Protonated Amides. Regioselective N-Activation of Medium-Bridged Twisted Lactams. Journal of the American Chemical Society, 132(26), 8836–8837. http://doi.org/10.1021/ja101690uen_US
dc.identifier.urihttp://hdl.handle.net/1808/24382
dc.descriptionThis document is the Accepted Manuscript version of a Published Work that appeared in final form in the Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://doi.org/10.1021/ja101690u.en_US
dc.description.abstractThe straightforward protonation of lactams by treatment with acid and the full structural characterization of three resulting N-protonated lactams are disclosed. This work provides experimental evidence that N-protonation of amide bonds results in a dramatic increase of non-planarity about the C-N amide bond. The resulting compounds are discussed in structural, spectroscopic, and reactivity terms. The data suggests that ca. 50° distortion of these amide bonds suffices for their efficient N-activation.en_US
dc.publisherAmerican Chemical Societyen_US
dc.titleStructural Characterization of N-Protonated Amides. Regioselective N-Protonated Amides. Regioselective N-Activation of Medium-Bridged Twisted Lactamsen_US
dc.typeArticleen_US
kusw.kuauthorSzostak, Michal
kusw.kuauthorYao, Lei
kusw.kuauthorDay, Victor W.
kusw.kuauthorPowell, Douglas
kusw.kuauthorAubé, Jeffrey
dc.identifier.doi10.1021/ja101690uen_US
dc.identifier.orcidhttps://orcid.org/0000-0003-1049-5767
dc.identifier.orcidhttps://orcid.org/0000-0001-7133-468X
kusw.oaversionScholarly/refereed, author accepted manuscripten_US
kusw.oapolicyThis item meets KU Open Access policy criteria.en_US
dc.identifier.pmidPMC2920036en_US
dc.rights.accessrightsopenAccess


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