Influence of the location of substituents in substituted celluloses on solution hydrolysis of the d-glucosidic linkages

✍ Scribed by Stanley P. Rowland; Phyllis S. Howley

• Book ID: 102992318
• Publisher: Elsevier Science
• Year: 1987
• Tongue: English
• Weight: 526 KB
• Volume: 165
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(87)80078-2

✦ Synopsis

Sensitivity of the D-glucosidic linkages in cellulose to hydrolysis in homogeneous acidic media was found to be directly related to the location of a substituent in the o-glucoyranosyl unit. The 2-diethylaminoethyl (DEAE) substituent caused sensitivity toward hydrolysis to decrease in the order o-glucose > 3-O >6-O-= 2-0-DEAE-o-glucopyranosyl-unit in hydrolyses beginning in 72% sulfuric acid and in 100% trilluoroacetic acid (TFA). Differences in the substituent effects were larger in TFA than in sulfuric acid. The effects reported for acid-catalyzed hydrolyses in homogeneous media are discussed relative to enzymic hydrolysis of a watersoluble, O-substituted cellulose.