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, β=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, β=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\(\bar v_{OH} = 3230, 3120, 2750 cm^{--1} \) for the solids,\(\bar v_{OH} = 3210, 3185, 2945 cm^{--1} \) for solutions (CCl4), and δOH=10.21, 10.53, 12.20 ppm for solutions (CCl4:CDCl3=5:1).
Zusammenfassung
Röntgenstrukturdaten von 2-Hydroxythiobenzoesäure (T=200 K;P21/a;a=14.903(5) Å,b=5.203(3) Å,c=9.114(6) Å, β=92.40(4)°;Z=4;R=0.049) und 2-Hydroxydithiobenzoesäure (T=297 K;P21/a;a=14.416(3) Å,b=13.447(3) Å,c=3.947(1) Å, β=90.96(2)°;Z=4;R=0.047) werden berichtet. In 2-Hydroxythiobenzoesäure sind jeweils zwei Moleküle über S-H...O=C Wasserstoffbrückenbindungen zu zyklischen Dimeren verbunden, in Analogie zum Assoziationsmuster von 2-Hydroxybenzoesäure. In 2-Hydroxydithiobenzoesäure sind die Moleküle hingegen über S-H...O(H)-C Wasserstoffbrückenbindungen zu Ketten verknüpft. Festkörper-IR-, und Lösungs-IR-und NMR-spektroskopische Daten von 2-Hydroxybenzoesäure, 2-Hydroxythiobenzoesäure und 2-Hydroxydithiobenzoesäure werden gegenübergestellt. Die wesentlichen Charakteristika der intramolekular assoziierten phenolischen O-H Gruppen der drei Titelverbindungen sind\(\bar v_{OH} = 3230, 3120, 2750 cm^{--1} \) für die Festkörper sowie\(\bar v_{OH} = 3210, 3185, 2945 cm^{--1} \) und δOH=10.21, 10.53, 12.20 ppm für Lösungen (CCl4 bzw. CCl4:CDCl3=5:1).
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Dedicated to Prof.O. Olaj on the occasion of his 60th birthday
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Mikenda, W., Steinwender, E. & Mereiter, K. Hydrogen bonding in 2-hydroxybenzoic, 2-hydroxythiobenzoic, and 2-hydroxydithiobenzoic acid. A structural and spectroscopic study. Monatsh Chem 126, 495–504 (1995). https://doi.org/10.1007/BF00807422
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DOI: https://doi.org/10.1007/BF00807422