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

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F68378271%3A_____%2F16%3A00462363" target="_blank" >RIV/68378271:_____/16:00462363 - isvavai.cz</a>

Alternative codes found

RIV/61388955:_____/16:00462363 RIV/00216208:11310/16:10326127

Result on the web

<a href="http://dx.doi.org/10.1107/S2053229616008767" target="_blank" >http://dx.doi.org/10.1107/S2053229616008767</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1107/S2053229616008767" target="_blank" >10.1107/S2053229616008767</a>

Result language

angličtina

Original language name

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

Original language description

Orthophthalaldehyde (o-phthalaldehyde, OPA) is an aromatic dialdehydenbearing two electron-withdrawing carbonyl groups. The reactions of OPA withnprimary amines are broadly applied for the synthesis of important heterocyclicncompounds with biological relevance. A number of such reactions have beenninvestigated recently and several structures of condensation products have beennreported, however, the complex reaction mechanism is still not fully understoodnand comprises concurrent as well as consecutive reactions. The reactionnproducts depend on the primary amine which reacts with OPA, the reactionnenvironment (solvent) and the proportion of the reactants. The title molecule,nC11H13NO, the product of the reaction of OPA with isopropylamine, contains anfive-membered pyrrole C4N ring with a carbonyl substituent, which forms part ofnthe isoindolinone unit. Though this pyrrole ring contains one C atom in the sp3-nhybridized state, it is fairly planar. The title molecule has been compared withnsimilar structures retrieved from the Cambridge Structural Database in order tonstudy this phenomenon. The planarity of this fragment has been explained bynthe presence of partially delocalized C—C, C—N and C—O bonds, and by anninner angle in the planar pentagonal ring ( 108 ), which is close to the idealntetrahedral value for the sp3-hybridized state of the constituent C atom. Due tonthis propitious angle, this C atom can be present in states intermediate betweennsp3- and sp2-hybridized in different structures, while still maintaining thenplanarity of the ring. There are only weak intermolecular C—H O hydrogennbonds and C—H -electron ring interactions in the structure. In particular, itnis the pyrrole ring which is involved in these interactions.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

BM - Solid-state physics and magnetism

OECD FORD branch

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Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2016

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Acta Crystallographica. Section C: Structural Chemistry

ISSN

2053-2296

e-ISSN

—

Volume of the periodical

C72

Issue of the periodical within the volume

7

Country of publishing house

US - UNITED STATES

Number of pages

7

Pages from-to

518-524

UT code for WoS article

000380286100003

EID of the result in the Scopus database

2-s2.0-84977178253