Silver(I) complexes based on diorganoselenium(II) ligands with amino or hydroxo functionalities

On the coordination behaviour of diorganoselenium ligands based on amino and azole functionalities: silver(i) complexes with relevance for biological applications

“…Compounds 2 and 3 are monomeric species in which the diorganoselenides act as N,Se,N -triconnective moieties (κ 2 N , N ′-κ Se coordination mode), 29 with selenium and both nitrogen atoms, one from the pendant arm (N1) and the other from the thiazole ring (N2) coordinated to silver. The Se–Ag interatomic distances show strong interactions in both complexes (2.7784(2) Å in 2 and 2.7967(3) Å in 3 , vs. ∑ r cov (Ag,Se) = 2.51 Å and ∑ r vdW (Ag,Se) = 3.60 Å), 30 with values in the range found for the closely related compounds [Ag(OTf){2-(Me 2 NCH 2 )C 6 H 4 } 2 Se] (2.6602(2) Å) 22 and [Ag(psbi) 2 ](BF 4 ) (psbi = 2-phenylselenomethyl-1 H -benzimidazole; Ag–Se1 2.923(1) Å and Ag–Se2 3.040(1) Å). 18 b The N–Ag interactions (N1–Ag1 2.2986(14) Å and N2–Ag1 2.3049(13) Å in 2 ; N1–Ag1 2.284(2) Å and N2–Ag1 2.282(2) Å in 3 ; vs. ∑ r cov (Ag,N) = 2.04 Å and ∑ r vdW (Ag,N) = 3.25 Å 30 ) are of a similar strength to those found in [Ag(OTf){2-(Me 2 NCH 2 )C 6 H 4 } 2 Se] (N1–Ag1 2.3706(15) Å and N2–Ag1 2.3040(15) Å), 22 or in [Ag(psbi) 2 ](BF 4 ) (Ag–N1 2.249(4) Å and Ag–N3 2.252(4) Å).…”

“…Compounds 2 and 3 are monomeric species in which the diorganoselenides act as N,Se,N-triconnective moieties (k 2 N,N 0 -kSe coordination mode), 29 with selenium and both nitrogen atoms, one from the pendant arm (N1) and the other from the thiazole ring (N2) coordinated to silver. The Se-Ag interatomic distances show strong interactions in both complexes 15) Å and N2-Ag1 2.3040(15) Å), 22 or in [Ag(psbi) 2 ](BF 4 ) (Ag-N1 2.249(4) Å and Ag-N3 2.252(4) Å). 18b The two complexes differ in the coordination behaviour of the anionic triflato ligand, e.g.…”

“…19 We have previously reported about homo-and heteroleptic diorganoselenium compounds bearing aryl groups decorated with one or two pendant arms capable for N-Se intramolecular interactions, e.g. 22 As a continuation of our work on this topic, we report herein on the synthesis and structural characterization of the new homoleptic diorganoselenide (PhtzCH 2 ) 2 Se (L7) as well as new silver(I) complexes of type [Ag(OTf)L], where L is a neutral diorganoselenide of type RSeR (6); and R = R 0 = CH 2 Phtz (7)). Our studies on their antiproliferative activity against the murine melanoma B16.F10 cells are also reported herein.…”

“…20 We were interested also in combining the structural characteristics of hypercoordinated selenium with the sterical and biological properties expected in the presence of pyrazole or phenylthiazole and we have recently reported on the synthesis and structural characterization of the homoleptic (pzCH 2 CH 2 ) 2 Se 20 and [(3,5-dmpz)CH 2 CH 2 ] 2 Se 21 and the heteroleptic diorganoselenides of types [2-(R 2 NCH 2 )C 6 H 4 ]Se(CH 2 CH 2 pz) and [2-(R 2 NCH 2 )C 6 H 4 ]Se(CH 2 Phtz), 20 as well as on the Ag( i ) complexes [Ag(OTf)L] (L = [(3,5-dmpz)CH 2 CH 2 ] 2 Se, [2-(R 2 NCH 2 )C 6 H 4 ]Se[(3,5-dmpz)CH 2 CH 2 ], 21 (pzCH 2 CH 2 ) 2 Se, 20 [2-(Me 2 NCH 2 )C 6 H 4 ] 2 Se). 22 As a continuation of our work on this topic, we report herein on the synthesis and structural characterization of the new homoleptic diorganoselenide (PhtzCH 2 ) 2 Se ( L7 ) as well as new silver( i ) complexes of type [Ag(OTf)L], where L is a neutral diorganoselenide of type RSeR′ (R = 2-(Me 2 NCH 2 )C 6 H 4 , R′ = CH 2 Phtz ( 1 ), CH 2 CH 2 pz ( 4 ); R = 2-(Et 2 NCH 2 )C 6 H 4 , R′ = CH 2 Phtz ( 2 ), CH 2 CH 2 pz ( 5 ); R = 2-[O(CH 2 CH 2 ) 2 NCH 2 ]C 6 H 4 , R′ = CH 2 Phtz ( 3 ), CH 2 CH 2 pz ( 6 ); and R = R′ = CH 2 Phtz ( 7 )). Our studies on their antiproliferative activity against the murine melanoma B16.F10 cells are also reported herein.…”

“…dmpzCH 2 CH 2 ) 2 Se}][NO 3 ] (N-Ag 2.22 Å and Se-Ag 2.63 Å) 33 and [Ag(NO 3 ){2-(Me 2 NCH 2 )C 6 H 4 } 2 Se] (N-Ag 2.30/2.37 Å and Se-Ag 2.66 Å) 22. The dimers are further connected through triflate bridges to other dimers with weak F4Á Á ÁH4 interactions of 2.7862(20) Å (vs. P r vdW (F,H) = 2.80 Å 30 ), thus forming chains of dimers (see the ESI, † Fig.…”