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Lattice energetics and thermochemistry of acridine derivatives and substituted acridinium trifluoromethanesulphonates

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Abstract

The enthalpies and temperatures of melting of eight 9-substituted acridines (alkyl, aryl or alkoxy) (I) and six their 10-methylated-acridinium trifluoromethanesulphonate (II) derivatives were measured by DSC. The enthalpies and temperatures of volatilisation of the first group of compounds were also determined by DSC or obtained by fitting TG curves to the Clausius–Clapeyron relationship. By combining the enthalpies of formation of gaseous acridines or 10-methylacridinium trifluoromethanesulphonate ions, obtained by the DFT method, and the corresponding enthalpies of sublimation and/or crystal lattice enthalpies, the enthalpies of formation of the compounds in the solid phase were predicted. For compounds whose crystal structures are known, experimental enthalpies of sublimation correspond reasonably well to crystal lattice enthalpies predicted theoretically as the sum of electrostatic, dispersive and repulsive interactions. Analysis of crystal lattice enthalpy contributions indicates that dispersive interactions between molecules always predominate in the case of acridine derivatives, whilst the crystal lattices of their quaternary salts are stabilised by electrostatic interactions between ions. Only in the case of 9-bromomethylacridine derivative, which crystallises in the monohydrated form, electrostatic contribution to the crystal lattice energy is significantly higher than in the other investigated acridines.

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Acknowledgements

The authors are grateful to Dr. Julian D. Gale for supplying the GULP program and permission to use it. They would also like to thank Mrs Gabriela Nowak-Wiczk for her contribution to the DSC and TG measurements. This study was financed from the State Funds for Scientific Research through National Science Centre grant 2011/03/D/ST4/02419 (contract No. UMO-2011/03/D/ST4/02419). Calculations were carried out on the computers of the Wroclaw Centre for Networking and Supercomputing (WCSS) (Grants No. 196 and 215).

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  1. Faculty of Chemistry, University of Gdańsk, Wita Stwosza 63, 80-308, Gdańsk, Poland

    Beata Zadykowicz & Piotr Storoniak

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  1. Beata Zadykowicz
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Correspondence to Beata Zadykowicz.

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Zadykowicz, B., Storoniak, P. Lattice energetics and thermochemistry of acridine derivatives and substituted acridinium trifluoromethanesulphonates. J Therm Anal Calorim 129, 1613–1624 (2017). https://doi.org/10.1007/s10973-017-6306-4

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