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Abundant polymorphism in a system with multiple hydrogen-bonding opportunities: Oxalyl dihydrazide

Ahn, Shinbyoung, Guo, Fang ORCID:, Kariuki, Benson ORCID: and Harris, Kenneth David Maclean ORCID: 2006. Abundant polymorphism in a system with multiple hydrogen-bonding opportunities: Oxalyl dihydrazide. Journal of the American Chemical Society 128 (26) , pp. 8441-8452. 10.1021/ja0573155

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To date, only one crystal structure has been reported in the literature for oxalyl dihydrazide [H2N·NH·CO·CO·NH·NH2]. In the present paper, we report the discovery of four new polymorphs of oxalyl dihydrazide, obtained by crystallization from solution under different conditions, including the use of different crystallization solvents. All polymorphs have the trans-trans-trans conformation of the N−N−C−C−N−N backbone, but the positions of the hydrogen atoms of the NH2 groups relative to this backbone differ between the different polymorphs through variation of the torsion angle around each NH−NH2 bond. The different polymorphs display a range of different hydrogen-bonding arrangements, constructed from different types of hydrogen-bonded array. The existence of several different potential hydrogen-bond donor and hydrogen-bond acceptor groups in the oxalyl dihydrazide molecule, together with the fact that the N−H bonds of the NH2 groups adopt different orientations with respect to the molecular plane, leads to several possible geometric permutations for hydrogen-bonding arrangements in the solid state. It would not be surprising if even more polymorphs of oxalyl dihydrazide are discovered in the future.

Item Type: Article
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: ACS
ISSN: 0002-7863
Last Modified: 18 Oct 2022 13:10

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