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

Kód výsledku v 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>

Nalezeny alternativní kódy

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

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

BM - Fyzika pevných látek a magnetismus

OECD FORD obor

—

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2016

Kód důvěrnosti údajů

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

Název periodika

Acta Crystallographica. Section C: Structural Chemistry

ISSN

2053-2296

e-ISSN

—

Svazek periodika

C72

Číslo periodika v rámci svazku

7

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

7

Strana od-do

518-524

Kód UT WoS článku

000380286100003

EID výsledku v databázi Scopus

2-s2.0-84977178253