Abstract
The generally thought unstable diol compound tetrazyl gem-diol (1, H2DTMdiol·2H2O), was firstly obtained in crystalline form by culturing the filtrate for ten days after acidification and filtration of aqueous solution of potassium salt of ketone (2, [K(HDTMone)·2H2O]n). The stability of this novel gem-diol compound is found owning to the hydrogen bonds with lattice water molecules and electrophilic tetrazolyl groups. Meanwhile, the undissolved ketone (3, H2DTMone) was separated during the filtration in the process of gem-diol compound production. Surprisingly, the crystal-to-crystal perfect transition phenomena from gem-diol (1) to ketone (3) were firstly observed after heating up to 120 °C as evidenced by X-ray single crystal diffraction and powder X-ray diffraction. These results found here might open new revenues for methylene oxidation and alkanediol chemistry.
Highlights
A very rare phenomenon was observed by chance at the attempt to develop new HEDMs
The electron withdrawing groups in the previously reported crystalline gem-diol compounds include trichloromethyl, pyridyl, ester group etc except tetrazyl[1,2,3,4,5,6,7]. This discovery is very important to gem-diol chemistry since none of crystalline tetrazyl gem-diol compound has been reported until now
Tetrazole and its derivatives have drawn researchers’ attention in developing HEDMs due to their high nitrogen content resulting the enrichment of high energy bonds such as N-N (160 kJ·mol−1) and N = N (418 kJ·mol−1)[11,12]
Summary
A very rare phenomenon was observed by chance at the attempt to develop new HEDMs (high-energy-density materials). White powder di(1H-tetrazol-5-yl)methanone (3, H2DTMone) can be obtained after acidification and filtration of solution of compound 2, since compound 3 hardly dissolves in water at room temperature. The crystalline tetrazyl gem-diol (-C(OH)2-) compound, di(1H-tetrazol-5-yl) methanediol dihydrate (1, H2DTMdiol·2H2O), was grown from the above filtrate in ten days.
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