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, JD ORCID: https://orcid.org/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

Preview

Text 187551_5190 Wallis PostPrint.pdf Download (559kB) | Preview

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

Actions (login required)

Edit View

Statistics

Views

Downloads