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https://hdl.handle.net/10356/87665
Title: | Understanding the origins of nucleophilic hydride reactivity of a sodium hydride-iodide composite | Authors: | Hong, Zonghan Ong, Derek Yiren Muduli, Subas Kumar Too, Pei Chui Chan, Guo Hao Tnay, Ya Lin Chiba, Shunsuke Nishiyama, Yusuke Hirao, Hajime Soo, Han Sen |
Keywords: | Sodium Hydride–Iodide Composite Powder X-ray Diffraction DRNTU::Science::Chemistry |
Issue Date: | 2016 | Source: | Hong, Z., Ong, D. Y., Muduli, S. K., Too, P. C., Chan, G. H., Tnay, Y. L., ... Soo, H. S. (2016). Understanding the origins of nucleophilic hydride reactivity of a sodium hydride-iodide composite. Chemistry - A European Journal, 22(21), 7108-7114. doi:10.1002/chem.201600340 | Series/Report no.: | Chemistry - A European Journal | Abstract: | Sodium hydride (NaH) has been commonly used as a Brønsted base in chemical syntheses, while it has rarely been employed to add hydride (H¢) to unsaturated electrophiles. We previously developed a procedure to activate NaH through the addition of a soluble iodide source and found that the new NaH–NaI composite can effect even stereoselective nucleophilic hydride reductions of nitriles, imines, and carbonyl compounds. In this work, we report that mixing NaH with NaI or LiI in tetrahydrofuran (THF) as a solvent provides a new inorganic composite, which consists of NaI interspersed with activated NaH, as revealed by powder X-ray diffraction, and both solid-state NMR and X-ray photoelectron spectroscopies. DFT calculations imply that this remarkably simple inorganic composite, which is comprised of NaH and NaI, gains nucleophilic hydridic character similar to covalent hydrides, resulting in unprecedented and unique hydride donor chemical reactivity. | URI: | https://hdl.handle.net/10356/87665 http://hdl.handle.net/10220/47059 |
ISSN: | 0947-6539 | DOI: | 10.1002/chem.201600340 | Schools: | School of Physical and Mathematical Sciences | Rights: | © 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the author created version of a work that has been peer reviewed and accepted for publication by Chemistry - A European Journal, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [http://dx.doi.org/10.1002/chem.201600340]. | Fulltext Permission: | open | Fulltext Availability: | With Fulltext |
Appears in Collections: | SPMS Journal Articles |
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File | Description | Size | Format | |
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Understanding the Origins of Nucleophilic Hydride Reactivity.pdf | 1.07 MB | Adobe PDF | View/Open |
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