THE STRENGTH OF ORGANIC BASES IN GLACIAL ACETIC ACID SOLUTION<sup>1</sup>

Hall, Norris F.

doi:10.1021/ja01375a072

Cited by 121 publications

(31 citation statements)

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“…Most investigatioizs of the basicities of aliphatic anzides have been carried out by titration (8) or indicator (9) methods using solutions in acetic or formic acids. However, it is not certain that the relative strengths of different Br#nsted bases are the same in these solvents as in water (10).…”

Section: Pimentioning

confidence: 99%

Ionization of Organic Compounds: Iii. Basicities of Propionic Acid and Propionamide

Edward¹,

Wang²

1962

Can. J. Chem.

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Protonation constants (pKBH+) of −6.8 and −0.9 have been determined for propionic acid and propionamide, respectively, from measurements of their ultraviolet absorption in various concentrations of sulphuric acid. The ionization ratio of propionamide and of other amides increases more slowly than the Hammett acidity function, h0, with increase in acid concentration. This may be explained by assuming that in a given concentration of sulphuric acid the protonated amide is more heavily hydrated than the protonated Hammett indicator used to establish the h0 scale for this region of acid concentrations.

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Section: Pimentioning

confidence: 99%

Ionization of Organic Compounds: Iii. Basicities of Propionic Acid and Propionamide

Edward¹,

Wang²

1962

Can. J. Chem.

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“…Any solvent of basic character, such as liquid ammonia or pyridine, produces a comparable effect, giving NH4+, C5H 5N I-I+, or in general solvated hydrogen ions. In a similar way, a solvent of acidic character, as for example glacial acetic acid, exer ts a leveling effect upon bases [8 to 10].…”

Section: Acid-base Reactions In Organic Solventsmentioning

confidence: 99%

“…Basic solvents exert a pronounced leveling effect upon acids but not upon bases. In some cases, basi c solvents exhibit weakly acidic properties and undergo slight au toprotolysis, as for example [11]: (10) 4. Acidic solvents.-Examples are concentrated sulfuric acid, glacial acetic acid, and other organic acids.…”

Section: Acid-base Reactions In Organic Solventsmentioning

confidence: 99%

“…A nalysis : 10 Preparation oj p henolphthalin n-butyl e ter.-Phenolphthalin (0.1 mole) was dissolved in 150 ml of hot n -butyl alcohol (comm ercial hi gh grade) . The solution was sa t urated wi th dry hydrogen chloride and h ea ted on th e steam bath for sev eral days.…”

Section: Preparation Oj Phenolphthalin Ethyl Ester (Iiimentioning

confidence: 99%

“…This behavior of the salt of trimethylamine oxide with bromphthalein magenta makes it readily distinguishable from solutions that contain the salt of bromphthalein magenta wi th unoxidized tertiary amines, such as tl'imethyl-or triethylamine. 10…”

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Acid-base reactions in benzene and other organic solvents: Behavior of bromphthalein magenta with different classes of organic bases

Davis¹,

Schuhmann²

1947

J. RES. NATL. BUR. STAN.

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Practical and theoretica l aspects of acid-base reactions in benzene and other organic solvents al'e discussed . The synthesis of the indicators bromphtha lein magenta E and B (the ethyl and n-butyl esters of t etrabromopheno lph thale in ) an d of their t etraalkylammonium salts is descri bed. Qualitative and spectrophotometric data concern in g the color reactions of the indicators with primary, seconda ry, and t ertia ry a li phatic amines , s ubstituted guan idines, a nd other n itrogen bases in benz ene and other types of organic solvents are presen ted. An expla nati on off ered for the color phenom ena is also appli cable to ulfon ephthalcins and other indicators.Examples are given of the qu antitative m eas urement of the relative reactivity of bases with bromphthal ein magenta in benzene. Illust rations a re furnishe d of the app li cation of the ind icato rs to the quantitative estimation of acids and bases, to measu rem ents of the relative s trengt,h s of orga ni c acids, and to the differen tiation o f primary, secondary, and tertiary a liphatic a mines.During t he sp ectrophotometric inves t igations, it was necessar y to des ign new types of a bsorption cells s uitable fo r vo latile solvents a nd for th in laye rs of solu t ion. A desc ription of the e cells is given.

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Basicity, hydrogen bonding and complex formation involving hydrazo, azo and azoxy groups

Krueger

1975

PATAI'S Chemistry of Functional Groups

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THE STRENGTH OF ORGANIC BASES IN GLACIAL ACETIC ACID SOLUTION¹

Cited by 121 publications

References 0 publications

Ionization of Organic Compounds: Iii. Basicities of Propionic Acid and Propionamide

Ionization of Organic Compounds: Iii. Basicities of Propionic Acid and Propionamide

Acid-base reactions in benzene and other organic solvents: Behavior of bromphthalein magenta with different classes of organic bases

Basicity, hydrogen bonding and complex formation involving hydrazo, azo and azoxy groups

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THE STRENGTH OF ORGANIC BASES IN GLACIAL ACETIC ACID SOLUTION1

Cited by 121 publications

References 0 publications

Ionization of Organic Compounds: Iii. Basicities of Propionic Acid and Propionamide

Ionization of Organic Compounds: Iii. Basicities of Propionic Acid and Propionamide

Acid-base reactions in benzene and other organic solvents: Behavior of bromphthalein magenta with different classes of organic bases

Basicity, hydrogen bonding and complex formation involving hydrazo, azo and azoxy groups

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THE STRENGTH OF ORGANIC BASES IN GLACIAL ACETIC ACID SOLUTION¹