Hydrogen bond formation in regioselectively functionalized 3-mono-O-methyl cellulose

Tetsuo Kondo, Andreas Koschella, Brigitte Heublein, Dieter Klemm, Thomas Heinze

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

The hydrogen bond systems of cellulose and its derivatives are one of the most important factors regarding their physical- and chemical properties such as solubility, crystallinity, gel formation, and resistance to enzymatic degradation. In this paper, it was attempted to clarify the intra- and intermolecular hydrogen bond formation in regioselectively functionalized 3-mono-O-methyl cellulose (3MC). First, the 3MC was synthesized and the cast film thereof was characterized in comparison to 2,3-di-O-methyl cellulose, 6-mono-O-methyl cellulose, and 2,3,6-tri-O-methyl cellulose by means of wide angle X-ray diffraction (WAXD) and 13C cross polarization/magic angle spinning NMR spectroscopy. Second, the hydrogen bonds in the 3MC film were analyzed by means of FTIR spectroscopy in combination with a curve fitting method. After deconvolution, the resulting two main bands (Fig. 3) indicated that instead of intramolecular hydrogen bonds between position OH-3 and O-5 another intramolecular hydrogen bond between OH-2 and OH-6 may exist. The large deconvoluted band at 3340 cm-1 referred to strong interchain hydrogen bonds involving the hydroxyl groups at C-6. The crystallinity of 54% calculated from the WAXD supports also the dependency of the usually observed crystallization in cellulose of the hydroxyl groups at C-6 to engage in interchain hydrogen bonding.

Original languageEnglish
Pages (from-to)2600-2604
Number of pages5
JournalCarbohydrate Research
Volume343
Issue number15
DOIs
Publication statusPublished - Oct 13 2008

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Methylcellulose
Hydrogen
Hydrogen bonds
Cellulose
X-Ray Diffraction
Hydroxyl Radical
Cellulose films
X ray diffraction
Fourier Transform Infrared Spectroscopy
Hydrogen Bonding
Magic angle spinning
Crystallization
Solubility
Curve fitting
Deconvolution
Spectrum Analysis
Chemical properties
Magnetic Resonance Spectroscopy
Nuclear magnetic resonance spectroscopy
Gels

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Cite this

Hydrogen bond formation in regioselectively functionalized 3-mono-O-methyl cellulose. / Kondo, Tetsuo; Koschella, Andreas; Heublein, Brigitte; Klemm, Dieter; Heinze, Thomas.

In: Carbohydrate Research, Vol. 343, No. 15, 13.10.2008, p. 2600-2604.

Research output: Contribution to journalArticle

Kondo, Tetsuo ; Koschella, Andreas ; Heublein, Brigitte ; Klemm, Dieter ; Heinze, Thomas. / Hydrogen bond formation in regioselectively functionalized 3-mono-O-methyl cellulose. In: Carbohydrate Research. 2008 ; Vol. 343, No. 15. pp. 2600-2604.
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