Acidity of ortho-substituted benzoic acids: an infrared and theoretical study of the intramolecular hydrogen bonds

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22340%2F06%3A00016736" target="_blank" >RIV/60461373:22340/06:00016736 - isvavai.cz</a>

Alternative codes found

RIV/61388963:_____/06:00041284

Result on the web

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DOI - Digital Object Identifier

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Result language

angličtina

Original language name

Acidity of ortho-substituted benzoic acids: an infrared and theoretical study of the intramolecular hydrogen bonds

Original language description

The structures of ortho-substituted benzoic acids with substituents bearing hydrogen atoms (OH, NH2, COOH and SO2NH2) were investigated by means of IR spectroscopy and of density functional theory at the B3LYP/6-311 + G(d,p) level. All possible conformations, hydrogen bonds, tautomeric forms and zwitterions were taken into consideration and particular attention was given to intramolecular H-bonds and their effect on acidity. Strong H-bonds in the anions of all four acids, were revealed by calculations.In three cases they were confirmed by the IR spectra of the tetrabutylammonium salts in tetrachloromethane solution, while the salt of 1,2-benzenedicarboxylic acid was not sufficiently soluble. The H-bonds are of different strengths but in all cases theyare the main cause of the strengthened acidity of these acids in the gas phase and also in solution, although their effect is opposed by weaker H-bonds present in the undissociated acid molecules. The substituent effect on the acidity wa

Czech name

Acidity of ortho-substituted benzoic acids: an infrared and theoretical study of the intramolecular hydrogen bonds

Czech description

The structures of ortho-substituted benzoic acids with substituents bearing hydrogen atoms (OH, NH2, COOH and SO2NH2) were investigated by means of IR spectroscopy and of density functional theory at the B3LYP/6-311 + G(d,p) level. All possible conformations, hydrogen bonds, tautomeric forms and zwitterions were taken into consideration and particular attention was given to intramolecular H-bonds and their effect on acidity. Strong H-bonds in the anions of all four acids, were revealed by calculations.In three cases they were confirmed by the IR spectra of the tetrabutylammonium salts in tetrachloromethane solution, while the salt of 1,2-benzenedicarboxylic acid was not sufficiently soluble. The H-bonds are of different strengths but in all cases theyare the main cause of the strengthened acidity of these acids in the gas phase and also in solution, although their effect is opposed by weaker H-bonds present in the undissociated acid molecules. The substituent effect on the acidity wa

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

Organic and Biomolecular Chemistry

ISSN

1477-0520

e-ISSN

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Volume of the periodical

2006

Issue of the periodical within the volume

4

Country of publishing house

GB - UNITED KINGDOM

Number of pages

9

Pages from-to

2003-2011

UT code for WoS article

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EID of the result in the Scopus database

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