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      Surface Tuning of Wood via Covalent Modification of Its Lignocellulosic Biopolymers with Substituted Benzoates—A Study on Reactivity, Efficiency, and Durability

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          Abstract

          Chemical modification of wood applying benzotriazolyl-activated carboxylic acids has proven to be a versatile method for the durable functionalization of its lignocellulosic biopolymers. Through this process, the material properties of wood can be influenced and specifically optimized. To check the scope and limitations of this modification method, various benzamide derivatives with electron-withdrawing (EWG) or electron-donating (EDG) functional groups in different positions of the aromatic ring were synthesized and applied for covalent modification of Scots pine ( Pinus sylvestris L.) sapwood in this study. The bonded amounts of substances (up to 2.20 mmol) were compared with the reactivity constants of the Hammett equation, revealing a significant correlation between the modification efficiency and the theoretical reactivity constants of the corresponding aromatic substitution pattern. The successful covalent attachment of the respective substituted benzamides was proven by attenuated total reflection infrared (ATR-IR) spectroscopy, while the stability of the newly formed ester bond was proven in a standardized leaching test.

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          The Effect of Structure upon the Reactions of Organic Compounds. Benzene Derivatives

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            A Reëxamination of the Hammett Equation.

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              Spectral characterization of eucalyptus wood.

              The main difficulties in wood and pulp analyses arise principally from their numerous components with different chemical structures. Therefore, the basic problem in a specific analytical procedure may be the selective separation of the main carbohydrate-derived components from lignin due to their chemical association and structural coexistence. The processing of the wood determines some structural modification in its components depending on the type of wood and the applied procedure. Fourier transform infrared (FT-IR) spectrometry and X-ray diffraction have been applied to analyze Eucalyptus g. wood chips and unbleached and chlorite-bleached pulp. The differences between samples have been established by examination of the spectra of the fractions obtained by successive extraction (acetone extractives, acetone free extractive samples, hemicelluloses, and lignins) by evaluating the derivative spectra, band deconvolution, etc. The energy and the hydrogen bonding distance have been evaluated. The relationship between spectral characteristics and sample composition has been established, as well as the variation of the degree of crystallinity after pulping and bleaching. The integral absorption and lignin/carbohydrate ratios calculated from FT-IR spectra of the IR bands assigned to different bending or stretching in lignin groups are stronger in the spectrum of eucalyptus chips than those from brown stock (BS) pulp spectra because of the smaller total amount of lignin in the latter. FT-IR spectra clearly show that after chlorite bleaching the structure of the wood components is partially modified or removed. Along with FT-IR data, the X-ray results confirmed the low content of lignin in the pulp samples by increasing the calculated values of the crystalline parameters. It was concluded that FT-IR spectroscopy can be used as a quick method to differentiate Eucalyptus globulus samples.
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                Author and article information

                Journal
                ACS Omega
                ACS Omega
                ao
                acsodf
                ACS Omega
                American Chemical Society
                2470-1343
                01 December 2021
                14 December 2021
                : 6
                : 49
                : 33542-33553
                Affiliations
                []Institute of Organic Chemistry, Clausthal University of Technology , Leibnizstraße 6, Clausthal-ZellerfeldD-38678, Germany
                []Bundesanstalt für Materialforschung und -prüfung (BAM) , Unter den Eichen 87, Berlin D-12205, Germany
                [§ ]Institute of Inorganic and Analytical Chemistry, Clausthal University of Technology , Paul-Ernst-Straße 4, Clausthal-Zellerfeld D-38678, Germany
                Author notes
                [* ]Email: dieter.kaufmann@ 123456tu-clausthal.de . Phone: +49-5323-722027.
                Author information
                https://orcid.org/0000-0002-6794-0748
                https://orcid.org/0000-0002-9790-828X
                Article
                10.1021/acsomega.1c04353
                8675034
                6dd6cfb2-48d8-49d5-b838-44ab4bdcfb43
                © 2021 The Authors. Published by American Chemical Society

                Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works ( https://creativecommons.org/licenses/by-nc-nd/4.0/).

                History
                : 12 August 2021
                : 03 November 2021
                Funding
                Funded by: Technische Universität Clausthal, doi 10.13039/501100018933;
                Award ID: NA
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                ao1c04353
                ao1c04353

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