1-Methyl-2,3-dihydro-1H-benzimidazole-2-selone

Abstract

The title compound C 8 H 8 N 2 Se, is the product of the reaction of 2-chloro-1-methyl­benzimidazole with sodium hydro­selenide. The mol­ecule is almost planar (r.m.s. deviation = 0.041 Å) owing to the presence of the long chain of conjugated bonds (Se=C—NMe—C=C—C=C—C=C—NH). The C=Se bond length [1.838 (2) Å] corresponds well to those found in the close analogs and indicates its pronounced double-bond character. In the crystal, mol­ecules form helicoidal chains along the b axis by means of N—H⋯Se hydrogen bonds.

Protolytic Cleavage of Hg–C Bonds Induced by 1-Methyl-1,3-dihydro-2H-benzimidazole-2-selone: Synthesis and Structural Characterization of Mercury Complexes

“… 27 However, in contrast to the numerous studies pertaining to 1-R-imidazole-2-thiones, there are few corresponding investigations of 1-R-imidazole-2-selones, H(seim R ). 28 − 32 For example, only H(seim Me ) 28 , 29 and H(seim Mes ), 29 and the benzannulated derivatives, H(sebenzim Me ) 30 , 31a and H(sebenzim Bu t ), 31a have been synthesized and structurally characterized (Figure 2 ). Moreover, there are very few examples of structurally characterized metal complexes that feature 1-R-imidazole-2-selone ligands.…”

“…1-R-imidazole-2-thiones, H­(mim R ), − of which the methyl derivative is the well-known antithyroid drug, methimazole (tapazole), , are a widely studied class of molecules that can bind to a variety of metals, − including mercury . However, in contrast to the numerous studies pertaining to 1-R-imidazole-2-thiones, there are few corresponding investigations of 1-R-imidazole-2-selones, H­(seim R ). − For example, only H­(seim Me ) , and H­(seim Mes ), and the benzannulated derivatives, H­(sebenz­im Me ) , and H­(se­benzim Bu t ), have been synthesized and structurally characterized (Figure ). Moreover, there are very few examples of structurally characterized metal complexes that feature 1-R-imidazole-2-selone ligands. ,− It is, therefore, appropriate to develop the chemistry of this class of ligands with respect to mercury.…”

Structural Characterization of 2-Imidazolones: Comparison with their Heavier Chalcogen Counterparts

“…2-Imidazolones, 2-imidazolethiones, and 2-imidazoleselones − belong to a class of five-membered heterocyclic nitrogen compounds that respectively feature exocyclic CO, CS, and CSe functional groups (Figure ) . In addition to these chalcogenone forms, the molecules also have potential for existing in equilibrium with their chalcogenol tautomers (Figure ), although the latter are typically less stable. − ,− Imidazolones , and imidazolethiones , possess various biological activities, with the latter having been most extensively studied because the methyl derivative, methimazole (tapazole), is a widely used antithyroid drug . Imidazoleselones have also received attention with respect to potential antithyroid activity, , and a derivative has been discovered in the blood of bluefin tuna .…”

“…In addition to these chalcogenone forms, the molecules also have potential for existing in equilibrium with their chalcogenol tautomers (Figure ), although the latter are typically less stable. − ,− Imidazolones , and imidazolethiones , possess various biological activities, with the latter having been most extensively studied because the methyl derivative, methimazole (tapazole), is a widely used antithyroid drug . Imidazoleselones have also received attention with respect to potential antithyroid activity, , and a derivative has been discovered in the blood of bluefin tuna . 2-Imidazolones, 2-imidazolethiones, , and 2-imidazoleselones are also capable of coordinating to metals, and one of our interests pertains to the ability to convert these compounds to multidentate ligands, namely, tris­(2-oxoimidazolyl)­hydroborato, [To R ], tris­(2-mercaptoimidazolyl)­hydroborato, [Tm R ], , and tris (2-selenoimidazolyl)­hydroborato ligands, [Tse R ], − which respectively provide [O 3 ], [S 3 ], and [Se 3 ] donor arrays .…”

Bromination of bis(pyridin-2-yl) diselenide in methylene chloride: the reaction mechanism and crystal structures of 1H-pyridine-2-selenenyl dibromide and its cycloadduct with cyclopentene (3aSR,9aRS)-2,3,3a,9a-tetrahydro-1H-cyclopenta[4,5][1,3]selenazolo[3,2-a]pyridinium bromide

“…5). The C2-Se1 distance of 1.927 (3) Å is typical for a single bond [in comparison, the lengths of the C Se bonds in related compounds are 1.817 (7) Å (Husebye et al, 1997), 1.8236 (11) Å (Mammadova et al, 2011) and 1.838 (2) Å (Mammadova et al, 2012)]. The N1-C2 and N1-C6 bond lengths are almost equal to each other because of the aromaticity of the cyclic system.…”