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Experimental and Theoretical Study of Selectivity in Mechanochemical Cocrystallization of Nicotinamide with Anthranilic and Salicylic Acid

Lukin, Stipe; Lončarić, Ivor; Tireli, Martina; Stolar, Tomislav; Blanco, Maria V.; Lazić, Predrag; Užarević, Krunoslav; Halasz, Ivan (2018) Experimental and Theoretical Study of Selectivity in Mechanochemical Cocrystallization of Nicotinamide with Anthranilic and Salicylic Acid. Crystal Growth and Design, 18 (3). pp. 1539-1547. ISSN 1528-7483

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Abstract

Selectivity in mechanochemical cocrystal formation between nicotinamide and anthranilic acid or salicylic acid was studied using tandem in situ reaction monitoring by powder X-ray diffraction (PXRD) and Raman spectroscopy. Selectivity was probed by offering a competing cocrystal coformer to a previously prepared cocrystal or under competitive reaction conditions where all cocrystal coformers, in different stoichiometric ratios, were introduced together in the starting reaction mixture. Reaction paths were dependent on the starting mixture composition, and we find that the formation of intermediates and the final product can be predicted from solid-state ab initio calculations of relative energies of possible reaction mixtures. In some cases, the quantitative assessment revealed different reaction profiles derived from PXRD and Raman monitoring, directly indicating, for the first time, different mechanochemical reactivity on the molecular and the bulk crystalline level of the reaction mixture.

Item Type: Article
Additional Information: Financial support from the Croatian Science Foundation (Grant No. UIP-2014-09-4744) is gratefully acknowledged. I.H. is grateful to the Adris foundation for supporting this work. S.L. is supported by the Croatian Science Foundation. I.L. and P.L. are supported by the Unity Through Knowledge Fund, Contract No. 22/15 and the H2020 CSA Twinning Project No. 692194, RBI-T-WINNING. We are grateful to the team at the fine-mechanics workshop of the Ruder Boskovic Institute for their continuous support and the staff of the 11-BM beamline for powder data collection of the salana cocrystal. Use of the Advanced Photon Source at Argonne National Laboratory was supported by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences, under Contract No. DE-AC02-06CH11357.
Uncontrolled Keywords: Mechanochemistry; Polymorphism; Cocrystals
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Physical Chemistry
Projects:
Project titleProject leaderProject codeProject type
Mehaniokemijska reaktivnost pod kontroliranim uvjetima temperature i atmosfere za čišću sintezu funkcionalnih materijala-MECHANOCONTROLKrunoslav UžarevićUIP-2014-09-4744HRZZ
Depositing User: Krunoslav Užarević
Date Deposited: 28 Nov 2019 13:30
Last Modified: 28 Nov 2019 13:30
URI: http://fulir.irb.hr/id/eprint/5165
DOI: 10.1021/acs.cgd.7b01512

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