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O- vs. N-protonation of 1-dimethylaminonaphthalene-8-ketones : formation of a peri N–C bond or a hydrogen bond to the pi-electron density of a carbonyl group
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Mercadal, Nerea, Day, Stephen Paul, Jarmyn, Andrew, Pitak, Mateusz B., Coles, Simon J., Wilson, Claire, Rees, Gregory J., Hanna, John V. and Wallis, John D. (2014) O- vs. N-protonation of 1-dimethylaminonaphthalene-8-ketones : formation of a peri N–C bond or a hydrogen bond to the pi-electron density of a carbonyl group. CrystEngComm, Volume 16 (Number 36). pp. 8363-8374. doi:10.1039/c4ce00981a ISSN 1466-8033.
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Official URL: http://dx.doi.org/10.1039/c4ce00981a
Abstract
X-ray crystallography and solid-state NMR measurements show that protonation of a series of 1-dimethylaminonaphthalene-8-ketones leads either to O protonation with formation of a long N–C bond (1.637–1.669 Å) between peri groups, or to N protonation and formation of a hydrogen bond to the π surface of the carbonyl group, the latter occurring for the larger ketone groups (C([double bond, length as m-dash]O)R, R = t-butyl and phenyl). Solid state 15N MAS NMR studies clearly differentiate the two series, with the former yielding significantly more deshielded resonances. This is accurately corroborated by DFT calculation of the relevant chemical shift parameters. In the parent ketones X-ray crystallography shows that the nitrogen lone pair is directed towards the carbonyl group in all cases.
Item Type: | Journal Article | ||||||||||
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Subjects: | Q Science > QD Chemistry | ||||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Physics | ||||||||||
Library of Congress Subject Headings (LCSH): | Carbonyl compounds | ||||||||||
Journal or Publication Title: | CrystEngComm | ||||||||||
Publisher: | Royal Society of Chemistry | ||||||||||
ISSN: | 1466-8033 | ||||||||||
Official Date: | 28 September 2014 | ||||||||||
Dates: |
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Volume: | Volume 16 | ||||||||||
Number: | Number 36 | ||||||||||
Number of Pages: | 12 | ||||||||||
Page Range: | pp. 8363-8374 | ||||||||||
DOI: | 10.1039/c4ce00981a | ||||||||||
Status: | Peer Reviewed | ||||||||||
Publication Status: | Published | ||||||||||
Access rights to Published version: | Restricted or Subscription Access | ||||||||||
Date of first compliant deposit: | 29 December 2015 | ||||||||||
Date of first compliant Open Access: | 29 December 2015 | ||||||||||
Funder: | Engineering and Physical Sciences Research Council (EPSRC), University of Warwick, Birmingham Science City, Advantage West Midlands (AWM), European Regional Development Fund (ERDF) | ||||||||||
Grant number: | EP/E018203/1 (EPSRC) |
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