The crystallography of acridine. I

Lowde, R. D.; Phillips, David; Wood, R.G.

doi:10.1107/s0365110x53001496

Cited by 31 publications

(24 citation statements)

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“…Furthermore, there is more than one molecular geometry, including different bond lengths and the degree of deviation from planarity, even within one crystal structure. 18 Apparently the acridine structure is rather mercurial, a character which is conducive to more than one reaction geometry substituted into a fluorene lattice. This aspect of the Ac/F reaction system requires further study.…”

Section: Kinetics At 150 Kmentioning

confidence: 99%

High pressure studies of the acridine/fluorene photoreaction: Vibration assisted tunneling

Chan

Dernis

Wong

et al. 1995

The Journal of Chemical Physics

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Articles you may be interested inThe highpressure range of the reaction of CH(2Π) with N2 High pressure range of addition reactions of HO. II. Temperature and pressure dependence of the reaction HO+COHOCO→H+CO2 High pressure range of the addition of HO to HO, NO, NO2, and CO. I. Saturated laser induced fluorescence measurements at 298 K High pressure studies of a hydrogentransfer photoreaction in a crystalline solid: Acridine/fluoreneWe report a multifaceted investigation of the hydrogen transfer photoreaction in acridine-doped fluorene crystals at higher temperature. The purpose is to elucidate the role of vibrationally assisted tunneling in this reaction system. Raman experiments were conducted at various pressures and 77 K to document the change of vibrational frequency for the promoting mode͑s͒. Upon compression, a line with a large pressure coefficient emerges from under the strong phonon mode at 96.5 cm Ϫ1 . Through polarization studies under pressure, we have identified it as a molecular butterfly mode of B 1 symmetry. We have measured the reaction rate at 150 K in order to examine the effect of a suggested promoting mode at ϳ440 cm Ϫ1 . The reaction rate again increases exponentially with pressure, but with a significantly higher pressure coefficient than that at 1.4 and 77 K. Mode patterns based on a recently published ͓J. Phys. Chem. 98, 12 223 ͑1994͔͒ normal coordinate analysis of fluorene are used to help establish the promoting modes for this reaction. This consideration suggests that the 95 and 238 cm Ϫ1 modes are likely promoting modes in addition to the 125 cm Ϫ1 libration. A computation of the Franck-Condon factor for the H-transfer process indicates that a small population of a high overtone of a promoting mode may make a disproportionally large contribution to the reaction rate. This calculation fails to account for the greater pressure coefficient of the reaction rate at higher temperature. Instead, such an increase may come partly from a greater compressibility at higher temperature.

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Section: Kinetics At 150 Kmentioning

confidence: 99%

High pressure studies of the acridine/fluorene photoreaction: Vibration assisted tunneling

Chan

Dernis

Wong

et al. 1995

The Journal of Chemical Physics

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“…Acridine is often used as a luminophore [3,4], electron-acceptor [5], and DNA-intercalator [6,7]. In crystallography, acridine is well known to crystallize in seven polymorphic forms [8][9][10][11][12][13][14]. The complicated polymorphism of acridine is due to various intermolecular interactions, i.e., p-p, CH-p, and CH-N interactions.…”

mentioning

confidence: 99%

Herringbone structures of 2,7-dihalogenated acridine tailored by halogen–halogen interactions

Yamamura

Ikuma

Nabeshima

2015

Journal of Molecular Structure

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“…These requirements are satisfied by the series anthraceneacridine-phenazine. The results of a crystallographic survey of several polymorphic modifications of acridine (see also Phillips, 1950;Lowde, Phillips & Wood, 1953) and phenazine are collected in Table 1. The cell constants listed in this table were obtained from the appropriate Weissenberg zero-level photographs, after extrapolation to 0 = 90°; the space groups were determined from zero-and n-level Weissenberg photographs.…”

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The crystal and molecular structures of heterocyclic compounds. I. The analysis of the crystal structure of α-phenazine

Herbstein¹,

Schmidt²

1955

Acta Cryst

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In a survey of heterocyclic compounds suited to both experimental and theoretical study of molecular dimensions, the crystallographic constants of two forms of phenazine and of four forms of acridine were measured. ~-Phenazine was chosen as the most suitable crystal structure for a detailed X-ray analysis.The intensities of 714 reflections (including 682 out of a possible total of 1024 within the limiting sphere for Cu Ks) were estimated visually. The structure problem was solved by the method of the molecular Fourier transform. Refinement was achieved in the hOl zone by Fourier methods and in the h/c0 and 0]d zones by the method of least squares. The coordinates from the two-dimensional analysis were refined by one least-squares treatment of the F(hkl) to a new set of coordinates, which corresponded to R(hkl) = O. 16. Final parameters were computed by one set'of Fo and Fc differential syntheses. The electron-density distribution in the best plane through the atomic centres was calculated by a direct Fourier method.The standard deviation a(x) of the final atomic coordinates was estimated to be 0.009 A; within the limits of error the molecule has symmetry mmm.The crystal and molecular structures of phenazine are discussed in Part II. IntroductionWhile encouraging agreement has recently been reported between observed and calculated bond lengths in aromatic hydrocarbons, a similar comparison in the heterocyclic series is difficult because of the lack of accurate experimental results for compounds suitable for theoretical study. Thus, in choosing compounds for a detailed analysis by X-ray methods we have confined our attention to molecules in which the perturbations introduced by the hetero-atom may be assumed small, and where a comparative study of a related, fully-investigated homocycllc system might be expected to facilitate theoretical work. These requirements are satisfied by the series anthraceneacridine-phenazine. The results of a crystallographic survey of several polymorphic modifications of acridine (see also Phillips, 1950;Lowde, Phillips & Wood, 1953) and phenazine are collected in Table 1. The cell constants listed in this table were obtained from the appropriate Weissenberg zero-level photographs, after extrapolation to 0 = 90°; the space groups were determined from zero-and n-level Weissenberg photographs. The data indicate that the most suitable compound for detailed study is a-phenazine, whose analysis by three-dimensional methods is reported in Part I of the present series. In Part II we discuss the crystal and molecular structures of phenazine and compare the experimental bond lengths with the theoretical values.

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The crystallography of acridine. I

Cited by 31 publications

References 0 publications

High pressure studies of the acridine/fluorene photoreaction: Vibration assisted tunneling

High pressure studies of the acridine/fluorene photoreaction: Vibration assisted tunneling

Herringbone structures of 2,7-dihalogenated acridine tailored by halogen–halogen interactions

The crystal and molecular structures of heterocyclic compounds. I. The analysis of the crystal structure of α-phenazine

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