Estimation of O-Acetyl and N-Acetyl and the Structure of Osazone Acetates

Wolfrom, M. L.; Konigsberg, M.; Soltzberg, S.

doi:10.1021/ja01294a030

Cited by 33 publications

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“…Simple procedures for the determination of 0acetyl groups in the presence of 7V-acetyl groups have been worked out by Kunz and Hudson 267 and by Wolfrom et al 268 Total acetyl groups can be determined by acid hydrolysis. The two types of acetyl residues are readily distinguishable on the basis of their lability to alkali.…”

Section: Determination Of N-and O-acetylmentioning

confidence: 99%

Analytical Methods for Carbohydrates

Aminoff¹,

Binkley²,

Schaffer³

et al. 1970

The Carbohydrates

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Section: Determination Of N-and O-acetylmentioning

confidence: 99%

Analytical Methods for Carbohydrates

Aminoff¹,

Binkley²,

Schaffer³

et al. 1970

The Carbohydrates

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“…The O-acetyl groups formed during an analytical acetylation may be selectively hydrolyzed in aqueous alkali-acetone mixtures at 0°C. in 1 hour; the JV-acetyl groups are not hydrolyzed under such conditions (15). The increase in the amount of standard acid required to back-titrate the alkali added for the selective hydrolysis, in comparison to a blank, is a measure of the acetylatable amino groups present.…”

Section: Analytical Proceduresmentioning

confidence: 99%

Functional Group Analysis: Characterization of Coal Hydrogenation Products

Glenn¹,

Olleman²

1954

Anal. Chem.

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“…The selective determination of 0-acetyl in the presence of N-acetyl has been accomplished by saponification with dilute alkali in aqueous acetone at 0' C. or atroomtemperature (3,78,181). The use of methoxyacetic anhydride for the acetylation followed by analysis of the product for methoxyl instead of acetyl was suggested by Hill (56).…”

Section: Classification Of Acylatios Procedures On Basis Of H L E 4 Rmentioning

confidence: 99%

Determination of Reactive Hydrogen in Organic Compounds

Olleman¹

1952

Anal. Chem.

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Methods for quantitatively determining reactive hydrogen in organic compounds have been reviewed to find the most suitable procedures for estimating the reactive structural units in coal degradation products. In the past, reaction with methylmagnesium iodide or lithium aluminum hydride has been used to determine total reactive hydrogen in organic compounds with an accuracy o f 1 3 to 5%. The types of compounds which have been determined are: alcohols, phenols, enols, mercaptans, acids. amines, amides, and water. Acylation methods. including acetylation, phthaloylation, benzoylation, ETHODS for quantitatively determiningreactive hydrogen in organic compounds-Le., hydrogen attached tonitrogen. oxygen, or sulfur and exceptionally reactive carbon-hydrogen structures-have been reviewed to find the most suitable procedures for estimating the reactive oxygen-and nitrogen-containing structures in coal degradation products. The chemical literature from 1927 to 1949, inclusive, has been thoroughly searched, and some earlier and more recent references have been consulted The literature previous to 1931 was reviewed by Meyer (93).Methyl Grignard reagents and lithium aluminum hydride will react quantitatively R ith reactive hydrogen atoms in organic compounds t o form methane and hydrogen, respectively. The gaa formed in each case is a memure of the "artive hydrogen." Other reagents have been reported for the determination of active hydrogen but are generally less satisfactory.Some of the active hydrogen atoms can also be replaced b i a(-yl groups, and compounds containing such hydrogen atoms are said to contain "acylatable hydrogen" or usually "acetylatable hydrogrn." ""wylatable hydrogen" and ' acetylatable hydrogen"are not strictly correct t e i m~, inaqmuch as the hydrogen is not acylated but rather replaced by an acyl group. However, these are convenient ternis which distinctly differentiate methods which involve acylation of reactive groups from the methods I T hich determine total "active hydrogen." Different reagents and conditions cause quantitative acylation of different functional groups, and consequently the terms "acylatable hydrogen" and "acetylatahle hydrogen" have little meaning unless the reagent and conditions are specified. Pa 1 Present addreas, Verona Research Center Koppers Co , Inc , Verona,formylation, and stearylation, vary greatly among themselves and give results depending on reagents and conditions. Variations of the most common method-i.e., acetylation using acetic anhydride and pyridine at approximately 100' C.-have been used to determine primary and secondary alcohols, "unhindered" phenols, and primary and secondary amines. Other acylation reagents may be advantageous if tertiary alcohols or pyrroles must be determined or selectivity of reaction is desired. Applicability of different acylation methods for determining functional groups has been tabulated.The methods of deterniining reactive hydrogen have thus been divided into two major groups-determinations of active hydrogrn and determinations o...

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Estimation of O-Acetyl and N-Acetyl and the Structure of Osazone Acetates

Cited by 33 publications

References 0 publications

Analytical Methods for Carbohydrates

Analytical Methods for Carbohydrates

Functional Group Analysis: Characterization of Coal Hydrogenation Products

Determination of Reactive Hydrogen in Organic Compounds

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