Počet záznamů: 1
A study of the planarity of the pyrrolone fragment in 2-isopropyl-2,3-dihydro-1H-isoindol-1-one
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SYSNO ASEP 0462363 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název A study of the planarity of the pyrrolone fragment in 2-isopropyl-2,3-dihydro-1H-isoindol-1-one Tvůrce(i) Donkeng Dazie, Joel (UFCH-W) RID, ORCID
Liška, Alan (UFCH-W) RID, ORCID
Ludvík, Jiří (UFCH-W) RID, ORCID
Fábry, Jan (FZU-D) RID, ORCID, SAI
Dušek, Michal (FZU-D) RID, ORCID, SAIZdroj.dok. Acta Crystallographica Section C-Structural Chemistry. - : Oxford Blackwell - ISSN 2053-2296
C72, č. 7 (2016), s. 518-524Poč.str. 7 s. Jazyk dok. eng - angličtina Země vyd. US - Spojené státy americké Klíč. slova isoindolinone ; isoindolone ; aromaticity Vědní obor RIV CG - Elektrochemie Vědní obor RIV – spolupráce Fyzikální ústav - Fyzika pevných látek a magnetismus CEP GA13-21704S GA ČR - Grantová agentura ČR LO1603 GA MŠMT - Ministerstvo školství, mládeže a tělovýchovy Institucionální podpora UFCH-W - RVO:61388955 ; FZU-D - RVO:68378271 UT WOS 000380286100003 EID SCOPUS 84977178253 DOI 10.1107/S2053229616008767 Anotace 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.Pracoviště Ústav fyzikální chemie J.Heyrovského Kontakt Michaela Knapová, michaela.knapova@jh-inst.cas.cz, Tel.: 266 053 196 Rok sběru 2017
Počet záznamů: 1