9-(tert-Butylamino)acridine

Abstract

The crystal structure of 9‐(tert‐butyl­amino)­acridine, C17H18N2, is composed of mol­ecules of the amino tautomeric form. The acridine moiety is slightly folded along the C⋯N line passing through opposite atoms of the central ring, and the orientation of the tert‐butyl­amino group makes the conjugation between the lone pair of the N atom and the acridine π‐system almost negligible. An intermolecular hydrogen bond, involving the exocyclic NH group as donor and the endocyclic N atom as acceptor, links the mol­ecules into infinite chains stretching along the b axis of the crystal.

2-Methylphenyl acridine-9-carboxylate

“…Table 1 gives parameters characterizing the geometries of the central acridine ring and the ester group. These are typical of acridine-based derivatives (Hempel et al, 1979;Meszko et al, 2002;Mrozek et al, 2002;Sikorski et al, 2005).…”

“…Since the phenyl fragment is removed during the oxidation of these compounds, it has been hypothesized that the phenyl ring substituents exert the greatest influence on the stability of 9-carboxy-10methylacridinium phenyl esters and their ability to chemiluminescence (Sato, 1996;Rak et al, 1999). Despite the long interest shown in this group of compounds, there are only two publications (by our own research team) on the crystallography of alkylphenyl-9-carboxylates (Meszko et al, 2002;Sikorski et al, 2005). It is thus important to extend investigations to further representatives of this group, especially in view of the fact that information on the structure, crystal packing and other features may help in the design of hydrolysis-resistant compounds able to react efficiently with oxidizing agents to produce light.…”

9-(Trichloroacetylimino)acridine monohydrate

“…1.7 (3) À4.0 1.0 (3) 22.3 2Notes: (I) 9-(trichloroacetylimino)acridine monohydrate (this work); (II) 9-acridinamine hemihydrate (Chaudhuri, 1983); (III) 9-(tert-butylamino)acridine (Meszko et al, 2002); (IV) 9-(phenylamino)acridine (Leardini et al, 1998); (V) 9-(dimethylamino)acridine (Rak et al, 1998); (VI) 10-methyl-9-(methylimino)acridine (Rak et al, 1998 (Kuma, 1989); cell refinement: KM-4 Software; data reduction: KM-4 Software;…”

“…Theory also predicts the co-existence of tautomeric forms in 9-aminoacridines monosubstituted at the exocyclic N atom (Rak et al, 1998). The structures of only two such derivatives have been determined, namely 9-(tert-butylamino)acridine (Meszko et al, 2002) and 9-(phenylamino)acridine (Leardini et al, 1998). It was found that crystals of these compounds are composed of molecules of the amino tautomer.…”

10-Methyl-9-(2-methylphenoxycarbonyl)acridinium trifluoromethanesulfonate

“…Table 1 gives parameters characterizing the geometries of the central acridine ring and the ester fragment. They are typical of acridine-based derivatives (Hempel et al, 1979;Meszko et al, 2002;Mrozek et al, 2002;Sikorski et al, 2005).…”