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231224s2016 xx |||||o 00| ||eng c |
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|a 10.1002/mrc.4318
|2 doi
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|a eng
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|a Sippl, Stefanie P
|e verfasserin
|4 aut
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| 245 |
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|a Kinetic and thermodynamic characterization of C-N bond rotation by N-methylacetohydroxamic acid in aqueous media
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|c 2016
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|a Text
|b txt
|2 rdacontent
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|a ƒaComputermedien
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|a ƒa Online-Ressource
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|a Date Completed 08.04.2016
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|a Date Revised 18.12.2015
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|a published: Print-Electronic
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|a Citation Status PubMed-not-MEDLINE
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|a Copyright © 2015 John Wiley & Sons, Ltd.
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|a Hydroxamic acids (HAs) perform tasks in medicine and industry that require bidentate metal binding. The two favored conformations of HAs are related by rotation around the C(=O)-N bond. The conformations are unequal in stability. Recently, we reported that the most stable conformation of a small secondary HA in water places the oxygen atoms anti to one another. The barrier to C-N bond rotation may therefore modulate metal binding by secondary HAs in aqueous media. We have now determined the activation barrier to C-N rotation from major to minor conformation of a small secondary HA in D2O to be 67.3 kJ/mol. The HA rotational barrier scales with solvent polarity, as is observed in amides, although the HA barrier is less than that of a comparable tertiary amide in aqueous solution. Successful design of new secondary HAs to perform specific tasks requires solid understanding of rules governing HA structural behavior. Results from this work provide a more complete foundation for HA design efforts
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|a Journal Article
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|a 1H
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|a Arrhenius analysis
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|a EXSY
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|a NMR
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|a hydroxamic acids
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|a rotational barrier
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|a variable temperature
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|a White, Paul B
|e verfasserin
|4 aut
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|a Fry, Charles G
|e verfasserin
|4 aut
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|a Volk, Sarah E
|e verfasserin
|4 aut
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|a Ye, Lingxiao
|e verfasserin
|4 aut
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|a Schenck, Heather L
|e verfasserin
|4 aut
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|i Enthalten in
|t Magnetic resonance in chemistry : MRC
|d 1985
|g 54(2016), 1 vom: 19. Jan., Seite 46-50
|w (DE-627)NLM098179667
|x 1097-458X
|7 nnns
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| 773 |
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|g volume:54
|g year:2016
|g number:1
|g day:19
|g month:01
|g pages:46-50
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|u http://dx.doi.org/10.1002/mrc.4318
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