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タイトル	en Molecular interactions with CO2 for controlling the regioselectivity of liquid phase hydrogenation of 2,4-dinitroaniline
作成者	en Yoshida, Hiroshi NRID 1000020027410 en Tomizawa, Akitoshi en Tachikawa, Hiroto NRID 1000010207045 en Fujita, Shin-ichiro NRID 1000080156869 en Arai, Masahiko NRID 1000060125490
アクセス権	open access
主題	NDC 571
内容注記	Abstract en The catalytic hydrogenation of 2,4-dinitroaniline using a 0.5 wt% Pt/TiO2 catalyst was investigated in a multiphase medium of tetrahydrofuran (THF) pressurized by CO2 at different pressures and at 323 K. When CO2 pressure was increased, the overall rate of hydrogenation simply decreased but the selectivity to the desired product of 4-nitro-1,2-phenylenediamine increased. The noticeable enhancement of the selectivity to 4-nitro-1,2-phenylenediamine can be explained by chemical reactivities of CO2 molecules. In situ high-pressure FTIR and molecular simulations demonstrate that the dissolved CO2 molecules may interact with amino groups of the substrate and weaken the intra-hydrogen bonding between the amino and 2-nitro groups, which results in the change in the relative reactivity of the two nitro groups, yielding the desired product in a higher selectivity. The change in the intra-and inter-molecular interactions between the substrate and CO2 molecules was theoretically examined by DFT calculations.
出版者	en Royal Society of Chemistry
日付	Issued2014-07-22
言語	eng
資源タイプ	journal article
出版タイプ	AM
資源識別子	HDL http://hdl.handle.net/2115/59539
関連	isVersionOf DOI https://doi.org/10.1039/c4cp02114b PMID 25092019
収録誌情報	PISSN 1463-9076 en Physical Chemistry Chemical Physics 巻16 号35 開始ページ18955 終了ページ18965
ファイル	fulltext Final version for PCCP (MS 5000).pdf 1.27 MB (application/pdf) Issued2014-07-22
コンテンツ更新日時	2023-07-26