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Nitrogen configuration determined by X‐ray analysis on an homogeneous series of 3‐Indolinones
Author(s) -
Carloni Patricia,
Greci Lucedio,
Stipa Pierluigi,
Cauzzi Daniele,
Rizzoli Corrado,
Sgarabotto Paolo
Publication year - 1996
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570330114
Subject(s) - chemistry , nitrogen , benzene , ring (chemistry) , conjugated system , reactivity (psychology) , x ray , crystallography , stereochemistry , organic chemistry , medicine , physics , alternative medicine , pathology , quantum mechanics , polymer
The X‐ray diffraction analyses of 2‐methyl‐2‐phenylindolin‐3‐one 1 , 1,2‐dimethyl‐2‐phenylindolin‐3‐one 2 , 1‐hydroxy‐2‐methyl‐2‐phenylindolin‐3‐one 3 and 1‐methoxy‐2‐methyl‐2‐phenylindolin‐3‐one 4 have been carried out and the structural data were compared with those of 1‐oxyl‐2‐methyl‐2‐phenylindolin‐3‐one 5 . The results demonstrate that only compounds 2 and 5 show planar trigonal geometry which is coplanar with the conjugated benzene ring of the indolinic nucleus, whereas compounds 3 and 4 show a marked pyramidality of the nitrogen. Even if compound 1 shows a certain pyramidality of the nitrogen, it has been considered similar to compound 2 . The reactivity of all studied compounds fit the structural data.