Conjugation of two functional groups through an unsaturated system

Result code in 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>

Alternative codes found

RIV/61388963:_____/06:00041090

Result on the web

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DOI - Digital Object Identifier

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Result language

angličtina

Original language name

Conjugation of two functional groups through an unsaturated system

Original language description

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;

Czech name

Conjugation of two functional groups through an unsaturated system

Czech description

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;

Type

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

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

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Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2006

Confidentiality

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

Name of the periodical

Journal of Physical Organic Chemistry

ISSN

0894-3230

e-ISSN

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Volume of the periodical

19

Issue of the periodical within the volume

1

Country of publishing house

US - UNITED STATES

Number of pages

9

Pages from-to

1-9

UT code for WoS article

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EID of the result in the Scopus database

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