Steric Effects and Steric Inhibition of Resonance: Structure and Ionization of 2-tert-Butylbenzoic Acid

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F01%3A00003930" target="_blank" >RIV/60461373:22310/01:00003930 - isvavai.cz</a>

Alternative codes found

RIV/61388963:_____/01:57010185

Result on the web

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DOI - Digital Object Identifier

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Result language

angličtina

Original language name

Steric Effects and Steric Inhibition of Resonance: Structure and Ionization of 2-tert-Butylbenzoic Acid

Original language description

Enhanced acidity of sterically hindered carboxylic acids has been explained by steric inhibition to resonance (SIR) and van der Waals (vdW) tension. These two terms have been quantitatively evaluated on a model comparing two isomers, 2-tert-butylbenzoicacid (3) and 4-tert-butylbenzoic acid (4). Energies and geometries of 3 and 4 and their anions have been calculated using the B3LYP model at a 6-31+G(d,p) or 6-311+G(3df,2pd) basis, both in minimum-energy conformations and with a constrained dihedral angle between the ring plane and carboxyl plane. From comparison of the two isomers it follows that SIR contributes significantly to the higher energy of 3, but also raises similarly the energy of its anion 3A.

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

CC - Organic chemistry

OECD FORD branch

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Project

<a href="/en/project/GA203%2F99%2F1454" target="_blank" >GA203/99/1454: Thermodynamics of substituent effects in water solution</a><br>

Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2001

Confidentiality

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

Name of the periodical

New Journal of Chemistry

ISSN

1144-0546

e-ISSN

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Volume of the periodical

N

Issue of the periodical within the volume

25

Country of publishing house

GB - UNITED KINGDOM

Number of pages

5

Pages from-to

250-254

UT code for WoS article

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EID of the result in the Scopus database

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