A study of the planarity of the pyrrolone fragment in 2-isopropyl-2,3-dihydro-1H-isoindol-1-one

0462363 - ÚFCH JH 2017 RIV US eng J - Článek v odborném periodiku
Donkeng Dazie, Joel - Liška, Alan - Ludvík, Jiří - Fábry, Jan - Dušek, Michal
A study of the planarity of the pyrrolone fragment in 2-isopropyl-2,3-dihydro-1H-isoindol-1-one.
Acta Crystallographica Section C-Structural Chemistry. C72, č. 7 (2016), s. 518-524. ISSN 2053-2296. E-ISSN 2053-2296
Grant CEP: GA ČR GA13-21704S; GA MŠMT LO1603
GRANT EU: European Commission(XE) CZ.2.16/3.1.00/24510
Institucionální podpora: RVO:61388955 ; RVO:68378271
Klíčová slova: isoindolinone * isoindolone * aromaticity
Kód oboru RIV: CG - Elektrochemie; BM - Fyzika pevných látek a magnetismus (FZU-D)
Impakt faktor: 4.099, rok: 2016

Orthophthalaldehyde (o-phthalaldehyde, OPA) is an aromatic dialdehyde
bearing two electron-withdrawing carbonyl groups. The reactions of OPA with
primary amines are broadly applied for the synthesis of important heterocyclic
compounds with biological relevance. A number of such reactions have been
investigated recently and several structures of condensation products have been
reported, however, the complex reaction mechanism is still not fully understood
and comprises concurrent as well as consecutive reactions. The reaction
products depend on the primary amine which reacts with OPA, the reaction
environment (solvent) and the proportion of the reactants. The title molecule,
C11H13NO, the product of the reaction of OPA with isopropylamine, contains a
five-membered pyrrole C4N ring with a carbonyl substituent, which forms part of
the isoindolinone unit. Though this pyrrole ring contains one C atom in the sp3-
hybridized state, it is fairly planar. The title molecule has been compared with
similar structures retrieved from the Cambridge Structural Database in order to
study this phenomenon. The planarity of this fragment has been explained by
the presence of partially delocalized C—C, C—N and C—O bonds, and by an
inner angle in the planar pentagonal ring ( 108 ), which is close to the ideal
tetrahedral value for the sp3-hybridized state of the constituent C atom. Due to
this propitious angle, this C atom can be present in states intermediate between
sp3- and sp2-hybridized in different structures, while still maintaining the
planarity of the ring. There are only weak intermolecular C—H O hydrogen
bonds and C—H -electron ring interactions in the structure. In particular, it
is the pyrrole ring which is involved in these interactions.
Trvalý link: http://hdl.handle.net/11104/0261873