Chiral and achiral crystals, charge-assisted hydrogen-bond patterns and self-organization of selected solid diaminium thiosulfates - Publikacja - MOST Wiedzy

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Chiral and achiral crystals, charge-assisted hydrogen-bond patterns and self-organization of selected solid diaminium thiosulfates

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Abstract A series of diaminium thiosulfates, derivatives of diamines: NH2CH2CH(CH3)NH2 (1) and NH2(CH2)nNH2, n = 3-6 (2-5 respectively)and thiosulfuric acid were prepared and their structures determined by crystal X-ray diffraction analysis. Compounds 1, 2 and 4 turned out to be hydrates. The crystal structure of 1,2-proylenediaminium thiosulfate is chiral and exhibits spontaneous resolution. Crystals for both enantiomers (1a and 1b) were obtained and examined. An extended network of strong, charge-assisted hydrogen bonding of the (+)N–H∙∙∙O(-) type (also O–H∙∙∙O and O–H∙∙∙S for hydrates) is most likely the main factor defining crystal packing and variable conformation of the cations. Formation of non-centrosymmetric hydrogen bond motifs – distorted cubans – seems to induce the formation of chiral solid state structure from achiral components in the case of 4. Diaminiumthiosulaftes with an odd number of carbon atoms in alkyl chain (compounds 1, 2, 4) form 3D supramolecular networks, while in the case of diaminium salts with an even number of carbon atoms (3 and 5), 2D layers of hydrogen bond domains are observed. The aminium thiosulfates were also characterized by elemental analysis, NMR, and FTIR spectroscopy. Conformations of α,ω-alkyldiaminiumcations in the solid state are discussed and rationalized by DFT calculations.

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Agnieszka Brozdowska, Jarosław Chojnacki. (2017). Chiral and achiral crystals, charge-assisted hydrogen-bond patterns and self-organization of selected solid diaminium thiosulfates, 73(3), 507-518. https://doi.org/10.1107/s2052520617004802

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Licencja

Copyright (International Union of Crystallography)

Informacje szczegółowe

Kategoria:
Publikacja w czasopiśmie
Typ:
artykuł w czasopiśmie wyróżnionym w JCR
Opublikowano w:
Język:
angielski
Rok wydania:
2017
Opis bibliograficzny:
Brozdowska A., Chojnacki J.: Chiral and achiral crystals, charge-assisted hydrogen-bond patterns and self-organization of selected solid diaminium thiosulfates// Acta Crystallographica Section B-Structural Science Crystal Engineering and Materials. -Vol. 73, iss. 3 (2017), s.507-518

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