CHELATE STABILITIES OF CERTAIN OXINETYPE COMPOUNDS. II. 4- HYDROXYBENZOTHIAZOLES

Journal Article · Sat May 20 04:00:00 EDT 1961 · Journal of the American Chemical Society (U.S.)

DOI:https://doi.org/10.1021/ja01471a002· OSTI ID:4053439

Lane, T J; C, C S; Sam, A

The acid dissociation constants of 4-hydroxybenzothiazole, 2- amino-4- hydroxybenzothiazole, 2-methylamino-4hydroxybenzothiazole, and 2-amino-4-hydroxy- 7-methylbenzothiazole were determined in 50% v/v p-dioxane at 25 and the chelate stability constants of the ligands with Cu(II), Pb(II), Ni(H), Co(II), Zn(II), and Cd(II) were obtained by Calvin-Bjerrum potentiometric titration technique. The results were compared with those previously reported for 8-hydroxyquinoline, 4-hydroxybenzimidazole, and 4-hydroxybenzoxazole. The stsbility constants of the 4-hydroxybenzothiazole chelates sre lower thsn those of the corresponding 8- hydroxyquinolinates. This is explained by larger nitrogen-oxygen distance and by unfavorable electron orientation on the donor nitrogen atom. The stability values are higher than those of 4-hydroxybenzimidazoles and 4-bydroxybenzoxazoles and this is attributed to the influence of the larger sulfur atom in the 1- position. (auth)

• Research Organization: Univ. of Notre Dame, Ind.
• Sponsoring Organization: USDOE
• NSA Number: NSA-15-020695
• OSTI ID: 4053439
• Journal Information: Journal of the American Chemical Society (U.S.), Journal Name: Journal of the American Chemical Society (U.S.) Vol. Vol: 83; ISSN JACSA
• Country of Publication: Country unknown/Code not available
• Language: English

Related Subjects

BENZIMIDAZOLES
BENZOTHIAZOLES
BENZOXAZOLES
CHEMISTRY
DIOXANE
ETHYLENE
HETEROCYCLICS
ISOMERS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXIDES
PHENOLS
POTENTIOMETRY
TITRATION