Steric Effects in Isolated Molecules: Gas-Phase Basicity of Methyl-Substituted Acetophenones

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F05%3A00013521" target="_blank" >RIV/60461373:22310/05:00013521 - isvavai.cz</a>

Alternative codes found

RIV/61388963:_____/05:00021133 RIV/00216275:25310/05:00002643

Result on the web

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DOI - Digital Object Identifier

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Result language

angličtina

Original language name

Steric Effects in Isolated Molecules: Gas-Phase Basicity of Methyl-Substituted Acetophenones

Original language description

The energies of 14 methyl-substituted acetophenones and of their protonated forms were calculated within the framework of the density functional theory at the B3LYP/6-311+G(d,p) level. The gas-phase basicities of some members of this series were measuredusing Fourier transform ion cyclotron resonance mass spectrometry in order to complete the known data. The protonated forms exist in two configurations differing in the position of the hydrogen atom; their equilibrium depends strongly on the substitution pattern. Taking into account all conformational equilibria, the experimental and calculated basicities agreed to within 2.7 kJ mol-1. Substituent effects were tentatively resolved into polar and steric contributions by comparing the corresponding orthoand para derivatives. The steric effect of the ortho-methyl groups defined in this way has a clear physical meaning proven by several correlations; it destabilizes the neutral acetophenone molecules but destabilizes the cations even more

Czech name

Steric Effects in Isolated Molecules: Gas-Phase Basicity of Methyl-Substituted Acetophenones

Czech description

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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

<a href="/en/project/LN00A032" target="_blank" >LN00A032: Structure and dynamics of complex molecular systems and biomolecules</a><br>

Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2005

Confidentiality

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

Name of the periodical

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

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Volume of the periodical

2005

Issue of the periodical within the volume

12

Country of publishing house

DE - GERMANY

Number of pages

9

Pages from-to

2580-2588

UT code for WoS article

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EID of the result in the Scopus database

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