Structural studies of peri-interactions and bond formation between electron-rich atomic centres and N-phenylcarboxamides or nitroalkenyl groups

O'LEARY, J., FORMOSA, X., SKRANC, W. and WALLIS, J.D., 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
Depositing User: EPrints Services
Date Added: 09 Oct 2015 09:46
Last Modified: 09 Jun 2017 13:10
URI: http://irep.ntu.ac.uk/id/eprint/2632

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