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Interactions between Functional Groups. Part III. The Structure of N , N ‐Dimethyl‐8‐nitro‐1‐naphthaleneamine in Seven Crystalline Environments
Author(s) -
Egli Martin,
Wallis John D.,
Dunitz Jack D.
Publication year - 1986
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19860690202
Subject(s) - chemistry , nitro , lone pair , conrotatory and disrotatory , molecule , group (periodic table) , crystal structure , stereochemistry , atom (system on chip) , crystallography , acceptor , ring (chemistry) , organic chemistry , alkyl , physics , computer science , embedded system , condensed matter physics
Abstract The N , N ‐dimethyl‐8‐nitro‐1‐naphthaleneamine molecule has been observed in seven environments in three crystal modifications. A range of conformations, related by conrotatory motions about the two exocyclic CN bonds, is observed. In all seven conformations, the lone pair of the amino N‐atom is directed approximately towards the nitro N‐atom, which is slightly pyramidalized towards the amino group. The NO 2 group appears to be a poorer through‐space electron acceptor than the carboxylic ester group, in contrast to their through‐bond electron‐accepting properties.