Thermochemistry and crystal lattice energetics of phenyl acridine-9-carboxylates and 9-phenoxycarbonyl-10-methylacridinium trifluoromethanesulphonates

Chemiluminogenic Properties of 10-Methyl-9-(phenoxycarbonyl)acridinium Cations in Organic Environments

“…33 Crystallographic data relevant to some of the derivatives discussed here are given elsewhere. [29][30][31][32][34][35][36] The chromatographic parameters of AE were established using a chromatographic set consisting of a Waters 600E Multisolvent Delivery System, a W2487 Dual λ Absorbance Detector (λ(obsd) ) 268, 254 nm), a Gemini 5 µm C6 phenyl 110 column (Phenomenex), and a 60/40 v/v % acetonitrile/water mixture containing 2 mM phosphates (Na 2 HPO 4 + NaHPO 4 , pH ) 3.5) as stationary and mobile phases, respectively. Retention times (R T ) and % areas under signals are presented as the average values of at least three runs.…”

“…Acridinium salts investigated (Scheme ) were synthesized starting from 2-methoxyacridine-9-carboxylic acid ( 1 − 3 : 2-methoxy-10-methyl-9-(phenoxycarbonyl)acridinium ( 1 ), 2-methoxy-10-methyl-9-[(2-methylphenoxy)carbonyl]acridinium ( 2 ), and 9-[(2-chlorophenoxy)carbonyl]-2-methoxy-10-methylacridinium ( 3 )) or acridine-9-carboxylic acid (Aldrich) ( 4 − 6 : 10-methyl-9-(phenoxycarbonyl)acridinium ( 4 ), 10-methyl-9-[(2-methylphenoxy)carbonyl]acridinium ( 5 ), and 9-[(2-chlorophenoxy)carbonyl]-10-methylacridinium ( 6 )) and the appropriate hydroxybenzene (Aldrich): phenol, 2-methylphenol, or 2-chlorophenol. ,, Detailed information concerning synthesis of the compounds and their analyses are given in the Supporting Information. Physicochemical properties concerning derivatives 4 − 6 are reported in some of our other papers: spectral, thermal , and NMR ( 1 H + 13 C) . Crystallographic data relevant to some of the derivatives discussed here are given elsewhere. − ,− …”

Structure, formation, thermodynamics and interactions in 9-carboxy-10-methylacridinium-based molecular systems

“…In the past, employing the same computational methodology as in the current study, we Please do not adjust margins Please do not adjust margins predicted E L for a series phenyl acridine-9-carboxylates and satisfactory correlations with the experimental data were found. 7 The theoretical lattice energies were also obtained for several 9-phenoxycarbonyl-10-methylacridinium triflates, containing CMA as a structural fragment. 7 However, for the latter compounds -similarly as in the case of compounds 1, 2 and 3 -experimental thermodynamic characteristics were not available.…”

“…7 The theoretical lattice energies were also obtained for several 9-phenoxycarbonyl-10-methylacridinium triflates, containing CMA as a structural fragment. 7 However, for the latter compounds -similarly as in the case of compounds 1, 2 and 3 -experimental thermodynamic characteristics were not available. In such cases computer-aided simulations appear to be the only strategy to gain information regarding thermodynamic properties of investigated crystals.…”

9-[(Mesityloxy)carbonyl]-10-methylacridinium trifluoromethanesulphonate and its derivative mesityl 9-methoxy-10-methyl-9,10-dihydroacridine-9-carboxylate: Structural and physicochemical features

“…The process (1 0 ) leading to separate ions (1(C) + 1(A)) is predicted to be highly endothermic (positive D r,298 H°) and forced (positive D r,298 G°) in the gaseous phase, but spontaneous (negative D r,298 G°) in CH 2 Cl 2 ( Table 5). The ions formed in reaction (1 0 ) interact electrostatically and dispersively; the energy of these interactions is 625 kJ/mol (the crystal lattice energy [49]). Lowering the D r,298 H°of reaction (1 0 ) (gaseous phase) by this value yields a value of À323 kJ/mol, which corresponds to the reaction of gaseous 4 and 5 leading to crystalline 1.…”