Conjugation of two functional groups through an unsaturated system

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22340%2F06%3A00016729" target="_blank" >RIV/60461373:22340/06:00016729 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61388963:_____/06:00041090

Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

Conjugation of two functional groups through an unsaturated system

Popis výsledku v původním jazyce

Energies of 51 1-(E),4-(E)-disubstituted 1,3-butadienes (1), 36 1,4-disubstituted benzenes (2) and 36 (E)-1,2-disubstituted ethenes (3) with dipolar substituents were calculated at the B3LYP/6-311 + G(d,p) level and evaluated in terms of isodesmic reactions expressing the interaction of substituents through the conjugated system. The energy of interaction reaches up to 40 kJ mol-1, it is roughly similar in the three series and most regular in the series 1. While its correlation within the framework of dual substituent parameter analysis lacks physical meaning, it is possible to separate the conjugative (resonance) component by subtracting the inductive component with reference to 1,4-disubstituted bicyclo[2.2.2]octanes 4. The conjugative interaction isstrongly stabilizing for the combination acceptor-donor and destabilizing for two donors; in these cases it is parallel to changes of geometry as they are predicted by the common resonance equations. Interaction of two acceptors is weak;

Název v anglickém jazyce

Conjugation of two functional groups through an unsaturated system

Popis výsledku anglicky

Energies of 51 1-(E),4-(E)-disubstituted 1,3-butadienes (1), 36 1,4-disubstituted benzenes (2) and 36 (E)-1,2-disubstituted ethenes (3) with dipolar substituents were calculated at the B3LYP/6-311 + G(d,p) level and evaluated in terms of isodesmic reactions expressing the interaction of substituents through the conjugated system. The energy of interaction reaches up to 40 kJ mol-1, it is roughly similar in the three series and most regular in the series 1. While its correlation within the framework of dual substituent parameter analysis lacks physical meaning, it is possible to separate the conjugative (resonance) component by subtracting the inductive component with reference to 1,4-disubstituted bicyclo[2.2.2]octanes 4. The conjugative interaction isstrongly stabilizing for the combination acceptor-donor and destabilizing for two donors; in these cases it is parallel to changes of geometry as they are predicted by the common resonance equations. Interaction of two acceptors is weak;

Druh

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

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

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Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2006

Kód důvěrnosti údajů

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

Název periodika

Journal of Physical Organic Chemistry

ISSN

0894-3230

e-ISSN

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Svazek periodika

19

Číslo periodika v rámci svazku

1

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

9

Strana od-do

1-9

Kód UT WoS článku

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EID výsledku v databázi Scopus

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