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Structural Characterization of N-Protonated Amides. Regioselective N-Protonated Amides. Regioselective N-Activation of Medium-Bridged Twisted Lactams
| dc.contributor.author | Szostak, Michal | |
| dc.contributor.author | Yao, Lei | |
| dc.contributor.author | Day, Victor W. | |
| dc.contributor.author | Powell, Douglas R. | |
| dc.contributor.author | Aubé, Jeffrey | |
| dc.date.accessioned | 2017-06-06T16:37:45Z | |
| dc.date.available | 2017-06-06T16:37:45Z | |
| dc.date.issued | 2010-07-07 | |
| dc.identifier.citation | Szostak, 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/ja101690u | en_US |
| dc.identifier.uri | http://hdl.handle.net/1808/24382 | |
| dc.description | This 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.abstract | The 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.publisher | American Chemical Society | en_US |
| dc.title | Structural Characterization of N-Protonated Amides. Regioselective N-Protonated Amides. Regioselective N-Activation of Medium-Bridged Twisted Lactams | en_US |
| dc.type | Article | en_US |
| kusw.kuauthor | Szostak, Michal | |
| kusw.kuauthor | Yao, Lei | |
| kusw.kuauthor | Day, Victor W. | |
| kusw.kuauthor | Powell, Douglas | |
| kusw.kuauthor | Aubé, Jeffrey | |
| dc.identifier.doi | 10.1021/ja101690u | en_US |
| dc.identifier.orcid | https://orcid.org/0000-0003-1049-5767 | |
| dc.identifier.orcid | https://orcid.org/0000-0001-7133-468X | |
| kusw.oaversion | Scholarly/refereed, author accepted manuscript | en_US |
| kusw.oapolicy | This item meets KU Open Access policy criteria. | en_US |
| dc.identifier.pmid | PMC2920036 | en_US |
| dc.rights.accessrights | openAccess |
