The stable inner salt 2,2-dimorpholino-2-ethylium-1-dithioate

Abstract

The title compound, C(10)H(16)N(2)O(2)S(2), is considered to maintain an inner-salt structure in the crystal, where the planes of the carbenium and the thiocarboxylate moieties are nearly perpendicular to each other [77 (2) degrees ], and the backbone C-C bond length [N(2)C-CS(2) 1.510 (2) A] is significantly shorter than a normal C-C single-bond length.

1,4-Bis(dimorpholinomethyl)benzene

“…The dihedral angle between the plane formed by C9, N1, N2 and the benzene ring plane is 78.87 (9)°. The bond angle of N2-C9-N1 is 107.7 (1)° and the bond length of the backbone C9-C10 is 1.520 (2) Å, which are comparable with those reported in the references (Fujihara et al, 2002;Ma et al, 2005). The morpholine rings adopt the usual chair conformation.…”

“…For related literature, see: Averkiev et al (2005); Bellon et al (1996); Fujihara et al (2002); Goodman & Jacobsen (2002); Lanman & Myers (2004); Ma et al (2005). Data collection: TEXRAY (Molecular Structure Corporation, 1985); cell refinement: TEXRAY; data reduction: TEXSAN (Molecular Structure Corporation, 1985); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97.…”

Carbene Complexes of Nonmetals

“…In each case, the CS 2 Ϫ group is nearly perpendicular to the NϪCϪN plane. The central CϪC bond lengths (151: 149.7 pm, [212c] 153: 149.8 pm, [216] 155 : 149.8, [213a] 158: 151.0 [217] ) appear to be slightly shorter than those of the analogous carboxylates.…”

2-{[2,2-Bis(diethylamino)ethan-2-yliumthioyl]sulfanyl}-1,1-bis(diethylamino)ethylium bis(perchlorate)

“…For general background to bis(N,N-disubstituted amino)carbeniumdithiocarboxylates, see: Winberg & Coffman (1965); Nagasawa et al (1995); Nakayama & Akiyama (1992); Nakayama et al (1997Nakayama et al ( , 2000; Nakayama (2000Nakayama ( , 2002; Miller et al (2000); Fujihara et al (2002); Siemeling et al (2012). For transition metal complexes, see: Miyashita et al (1998); Banerjee et al (2002); Fujihara et al (2004); Sugaya et al (2009).…”

“…, which have a zwitterionic (inner-salt) form and a neutral form as canonical structures (Nagasawa et al, 1995;Fujihara et al, 2002), are structurally and reactively interesting (Winberg & Coffman, 1965;Otani et al, 1998;Nakayama & Akiyama, 1992;Nakayama et al, 2000;Nakayama, 2000Nakayama, , 2002Banerjee & Zubieta, 2004;Siemeling et al, 2012). We have reported the syntheses, structures, and properties of the various transition metal complexes using (R 2 N) 2 C 2 S 2 as ligands (Miyashita et al, 1998;Banerjee et al, 2002;Fujihara et al, 2004;Sugaya et al, 2009), and the ligands act as neutral monodentate, bridging, and chelating ligands maintaining the characteristic zwitterionic form.…”