Intramolecular Hydrogen Bonding in Benzoxazines: When Structural Design Becomes Functional

Chemistry : a European Journal
Pablo FroimowiczHatsuo Ishida

Abstract

The future evolution of benzoxazines and polybenzoxazines as advanced molecular, structural, functional, engineering, and newly commercial materials depends to a great extent on a deeper and more fundamental understanding at the molecular level. In this contribution, the field of benzoxazines is briefly introduced along with a more detailed review of ortho-amide-functional benzoxazines, which are the main subjects of this article. Provided in this article are the detailed and solid scientific evidences of intramolecular five-membered-ring hydrogen bonding, which is supposed to be responsible for the unique and characteristic features exhibited by this ever-growing family of ortho-functionalized benzoxazines. One-dimensional (1D) (1) H NMR spectroscopy was used to study various concentrations of benzoxazines in various solvents with different hydrogen-bonding capability and at various temperatures to investigate in detail the nature of hydrogen bonding in both ortho-amide-functionalized benzoxazine and its para counterpart. These materials were further investigated by two-dimensional (2D) (1) H-(1) H nuclear Overhauser effect spectroscopy (NOESY) to verify and support the conclusions derived during the 1D (1) H NMR experiments. ...Continue Reading

References

Mar 1, 2006·Angewandte Chemie·Chih-Feng WangFeng-Chih Chang
Jun 6, 2008·Bioresource Technology·Chanchira JubsilpSarawut Rimdusit
Nov 11, 2009·Analytical Chemistry·Eun Su ParkGale Holmes
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Dec 3, 2014·Chemical Communications : Chem Comm·Penghua CheJie Xu

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Citations

Jan 3, 2018·Chemical Communications : Chem Comm·K MartinaE Colacino
Jul 13, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ben E SmithGregory S Tschumper
May 1, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Poul Erik Hansen

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