- Lattice energetics and thermochemistry of acridine derivatives and substituted acridinium trifluoromethanesulphonates
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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.
- Zadykowicz, Beata,Storoniak, Piotr
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p. 1613 - 1624
(2017/08/16)
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- Structural considerations on acridine/acridinium derivatives: Synthesis, crystal structure, Hirshfeld surface analysis and computational studies
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This article describes a detailed study of the molecular packing and intermolecular interactions in crystals of four derivatives of acridine, i.e. 9-methyl-, 9-ethyl, 9-bromomethyl- and 9-piperidineacridine (1, 2, 3 and 4, respectively) and three 10-methy
- Wera, Micha?,Storoniak, Piotr,Serdiuk, Illia E.,Zadykowicz, Beata
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- Antitumour polycyclic acridines. Part 9. Synthesis of 7H-pyrido[4,3,2-kl]acridines with basic side chains
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[3 + 2] Cycloaddition of 3-(dialkylamino)-1-triphenylphosphoranylidenepropan-2-ones and 9-azidoacridine affords 9-[5-(dialkylaminomethyl)-1H-1,2,3-triazol-1-yl]acridines. Graebe-Ullmann thermolysis of the triazoles has been guided by differential scanning calorimetry to predict the optimum temperature for nitrogen extrusion. Boiling diphenyl ether (bp 259°C) is a suitable solvent to convert the triazolylacridines to 2-(dialkylaminomethyl)-7H-pyrido[4,3,2-kl]acridines.
- Ellis, Michael J.,Stevens, Malcolm F.G.
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p. 3174 - 3179
(2007/10/03)
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