Hydrogen bonding in 2-hydroxybenzoic, 2-hydroxythiobenzoic,and 2-hydroxydithiobenzoic acid. A structural and spectroscopic study |
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Authors: | W Mikenda E Steinwender K Mereiter |
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Institution: | (1) Institut für Organische Chemie, Universität Wien, A-1090 Vienna, Austria;(2) Chemserv, A-4021 Linz, Austria;(3) Institut für Mineralogie, Kristallographie und Strukturchemie, Technische Universität Wien, A-1060 Vienna, Austria |
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Abstract: | Summary X-ray structural data are reported for 2-hydroxythiobenzoic acid (T=200 K;P21/a;a=14.903(5) Å,b=5.203(3) Å,c=9.114(6) Å, =92.40(4)°;Z=4;R=0.049) and 2-hydroxydithiobenzoic acid (T=297 K;P21/a;a=14.416(3) Å,b=13.447(3) Å,c=3.947(1) Å, =90.96(2)°;Z=4;R=0.047). In 2-hydroxythiobenzoic acid, each two molecules form cyclic dimersvia S-H...O=C hydrogen bonds, analogous to the association pattern of 2-hydroxybenzoic acid. In 2-hydroxydithiobenzoic acid, the molecules are linked to chains by S-H...O(H)-C hydrogen bonds. Solid state IR, and solution IR and NMR spectroscopic data of 2-hydroxybenzoic acid, 2-hydroxythiobenzoic acid, and 2-hydroxydithiobenzoic acid are summarized. The main characteristics of the intramolecularly associated phenolic O-H groups of the three title compounds are
for the solids,
for solutions (CCl4), and OH=10.21, 10.53, 12.20 ppm for solutions (CCl4:CDCl3=5:1).Dedicated to Prof.O. Olaj on the occasion of his 60th birthday |
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Keywords: | Hydrogen bonding 2-Hydroxy(di(thio))benzoic acid IR spectra NMR spectra X-ray diffraction |
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