Piperazine-1,4-diol (PipzDiol): synthesis, stereodynamics and assembly of supramolecular hydrogen-bonded 2D networks

Piperazine-1,4-diol (PipzDiol): synthesis, stereodynamics and assembly of supramolecular hydrogen-bonded 2D networks Full article

Journal

New Journal of Chemistry
ISSN: 1369-9261 , E-ISSN: 1144-0546

Output data

Year: 2022, Volume: 46, Number: 42, Pages: 20386-20394 Pages count : 9 DOI: 10.1039/d2nj03012h

Authors

Lesnikov Vladislav K. ¹ , Nelyubina Yulia V. ² , Sukhorukov Alexey Yu. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Leninsky prospect, 47, Moscow, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova str. 28, 119991, Moscow, Russian Federation

Piperazine (Pipz) is widely used as a building block for the self-assembly of supramolecular hydrogen-bonded crystalline networks. Here, piperazine-1,4-diol (PipzDiol) has been suggested as an analog of piperazine with an extended H-bond donor geometry. A convenient synthesis of PipzDiol has been developed and the compound has been fully characterized. Structural and stereodynamic studies showed that PipzDiol exists in solution as a dynamic mixture of conformers/invertomers. The formation of co-crystals with acids is accompanied by preferable selection of one stereoisomeric form depending on the nature of the co-former. Piperazine and PipzDiol were found to form distinct supramolecular H-bonded networks with topologically different H-bonded motifs. In crystalline adducts with sulfuric, oxalic, and para-aminobenzoic acids, piperazine forms 3D H-bonded networks, while 2D layers are assembled with PipzDiol.

Lesnikov V.K. , Nelyubina Y.V. , Sukhorukov A.Y.
Piperazine-1,4-diol (PipzDiol): synthesis, stereodynamics and assembly of supramolecular hydrogen-bonded 2D networks
New Journal of Chemistry. 2022. V.46. N42. P.20386-20394. DOI: 10.1039/d2nj03012h WOS Scopus OpenAlex

Web of science:	WOS:000869279900001
Scopus:	2-s2.0-85141355967
OpenAlex:	W4313061061

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