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2,4′:2′,4 Dianhydride of 3-keto-glucoside, a precursor to chromophores of aged, yellow cellulose, and its weak interactions

Cellulose (London), 2017-03, Vol.24 (3), p.1227-1234 [Peer Reviewed Journal]

Springer Science+Business Media Dordrecht (outside the USA) 2017 ;Copyright Springer Science & Business Media 2017 ;Cellulose is a copyright of Springer, (2017). All Rights Reserved. ;ISSN: 0969-0239 ;EISSN: 1572-882X ;DOI: 10.1007/s10570-017-1198-9

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Title:
2,4′:2′,4 Dianhydride of 3-keto-glucoside, a precursor to chromophores of aged, yellow cellulose, and its weak interactions
Author: Rosenau, Thomas ; Potthast, Antje ; Kosma, Paul ; Hosoya, Takashi ; Henniges, Ute ; Mereiter, Kurt ; French, Alfred D.
Subjects: Bioorganic Chemistry ; Carbonyl groups ; Carbonyls ; Cellulose ; Ceramics ; Chemistry ; Chemistry and Materials Science ; Chromophores ; Cleavage ; Composites ; Crosslinking ; Crystals ; Dianhydrides ; Diketones ; Dodecane ; Glass ; Glucosides ; Hydrogen bonds ; Natural Materials ; Organic Chemistry ; Original Paper ; Oxygen atoms ; Physical Chemistry ; Polymer Sciences ; Precursors ; Quinones ; Sustainable Development ; Yellowing
Is Part Of: Cellulose (London), 2017-03, Vol.24 (3), p.1227-1234
Description: Studies of cellulose aging and yellowing that involved a 1,4-dimethyl 3-keto β- d -glucoside (compound 1 ) model of oxidized cellulose led to a hemi-hydrated crystal of title compound 2 (1,6-dihydroxy-3,8-bis-hydoxymethyl-5,10-dimethoxy-4,9-dioxa-tricyclo [5,3,1,1,2,6] dodecane-11,12-dione). The same compound 2 was isolated in low yield from “real-world” oxidized and aged cellulosic pulp. Formation of compound 2 implies cellulose chain cleavage and, unexpectedly, cross-linking during aging. X-ray diffraction revealed an encompassing 10-membered ring whose two carbonyl group bridges define two eight-membered rings and three six-membered rings. The central six-membered ring is antecedent to 2,5-dihydroxy-1,4-benzoquinone (compound 3 ), a potent and nearly ubiquitous chromophore in aged cellulose; the outer rings derive from the keto-glucosides and have 4 C 1 and 1 C 4 shapes with gt and rare tg O-6 positions. Weak trans-annular interactions between >C=O carbon and ring oxygen atoms were confirmed with Atoms-in-Molecules theory. That theory was also used to analyze a questionable cyclic hydrogen bond and bonds between adjacent O–H and carbonyl oxygens.
Publisher: Dordrecht: Springer Netherlands
Language: English
Identifier: ISSN: 0969-0239
EISSN: 1572-882X
DOI: 10.1007/s10570-017-1198-9
Source: ProQuest Central

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2,4′:2′,4 Dianhydride of 3-keto-glucoside, a precursor to chromophores of aged, yellow cellulose, and its weak interactions

Springer Science+Business Media Dordrecht (outside the USA) 2017 ;Copyright Springer Science & Business Media 2017 ;Cellulose is a copyright of Springer, (2017). All Rights Reserved. ;ISSN: 0969-0239 ;EISSN: 1572-882X ;DOI: 10.1007/s10570-017-1198-9

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