title: Structural studies of peri-interactions and bond formation between electron-rich atomic centres and N-phenylcarboxamides or nitroalkenyl groups.
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.
authors.affiliation: School of Biomedical and Natural Sciences, The Nottingham Trent University, Clifton Lane, Nottingham, NG11 8NS, UK.
authors.forename: Jane
authors.initials: J
authors.lastname: O'Leary
authors.forename: Xavier
authors.initials: X
authors.lastname: Formosa
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Skranc
authors.forename: John D
authors.initials: JD
authors.lastname: Wallis