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O'Leary, J., Formosa, X., Skranc, W. and Wallis, J.D. 
ORCID: 0000-0001-7259-8783,
2005.
Structural studies of peri-interactions and bond formation between electron-rich atomic centres and N-phenylcarboxamides or nitroalkenyl groups.
Organic and Biomolecular Chemistry, 3 (18), pp. 3273-3283.
ISSN 1477-0520
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Abstract
Structural studies of peri-interactions with dimethylamino groups in naphthalene systems indicate that the N-phenylcarboxamide group has a through-space electron attracting power closer to that of a carboxylic ester than a N,N-dialkylcarboxamide, while 2-nitroalkenyl groups have a lower through-space electron attracting power. However, addition of a benzoyl group to the 2-position of the nitroethenyl group leads to cyclisation to give a zwitterion, in which the carbanion is stabilised by full conjugation with the nitro group and partial conjugation with the carbonyl group. An interesting case where a steric interaction overrides an electrophile/nucleophile attraction is also described. The limitations to the interpretation of short contact distances from crystallographic measurements are discussed.
| Item Type: | Journal article |
|---|---|
| Publication Title: | Organic and Biomolecular Chemistry |
| Creators: | O'Leary, J., Formosa, X., Skranc, W. and Wallis, J.D. |
| Publisher: | Royal Society of Chemistry |
| Place of Publication: | Cambridge |
| Date: | 2005 |
| Volume: | 3 |
| Number: | 18 |
| ISSN: | 1477-0520 |
| Divisions: | Schools > School of Science and Technology |
| Record created by: | EPrints Services |
| Date Added: | 09 Oct 2015 09:46 |
| Last Modified: | 09 Jun 2017 13:10 |
| URI: | https://irep.ntu.ac.uk/id/eprint/2632 |
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