Issue 2, 1984
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Infrared and 1H nuclear magnetic resonance studies of hydrogen bonds in some pyridine N-oxide trifluoroacetates and trichloroacetates in chloroform. Correlation of OH stretching frequencies and proton chemical shifts with pyridine N-oxide pKa values

Bogumił Brycki  and  Mirosław Szafran  

Abstract

The i.r. and 1H n.m.r. spectra are reported for the trifluoro-and trichloro-acetates of 12 substituted pyridine N-oxides in dry chloroform. If the centre of gravity of the OH stretching absorption ([small nu, Greek, tilde]H)and the chemical shift of hydrogen-bonded protons (δ) are plotted against the pKa value of the N-oxides, the points fall on two intersecting straight lines. The correlations reflect changes in the hydrogen-bond strength. Plots of [small nu, Greek, tilde]H and δ of trifluoroacetates against the corresponding values for the trichloroacetates are used to show that the proton-donor properties of the acids are comparable. A direct plot of δversus[small nu, Greek, tilde]H gives a straight line consistent with data for the monomeric acids. This correlation is discussed with respect to the difference between hydrogen bonds in molecular and ion-pair complexes.

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Article information

DOI
https://doi.org/10.1039/P29840000223
Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1984, 223-226

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Infrared and 1H nuclear magnetic resonance studies of hydrogen bonds in some pyridine N-oxide trifluoroacetates and trichloroacetates in chloroform. Correlation of OH stretching frequencies and proton chemical shifts with pyridine N-oxide pKa values

B. Brycki and M. Szafran, J. Chem. Soc., Perkin Trans. 2, 1984, 223 DOI: 10.1039/P29840000223

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