Ethyl 2-[[2-(3-nitrophenyl)-5-phenyl-1H-imidazol-4-yl]sulfanyl]acetate: synthesis via a microwave-mediated combinatorial chemistry approach.
The orange title compound, C(19)H(17)N(3)O(4)S, can be synthesized either via microwave-mediated combinatorial chemistry strategies or conventional synthetic procedures. The phenyl and meta-nitrophenyl C(6) rings are essentially coplanar with the central imidazolyl ring, with interplanar angles of 0.87 (5) and 0.97 (4), respectively, resulting in optimum conjugation (SCH(2) moiety included); lambda(max) = 281 nm in CH(3)CN. The principal intermolecular interactions are N(imid)-H...O(nitro) and N(imid)-H...O[double bond]C [N...O = 3.058 (2) and 3.432 (3) A, and N-H...O = 128 and 153, respectively]. The closest H.S distance is an intramolecular C-H...S contact, with H...S = 2.54 A and C-H...S = 136.
Gallagher
John F
JF
School of Chemical Sciences, Dublin City University, Dublin 9, Ireland. john.gallagher@dcu.ie
Coleman
Clare M
CM
O'Shea
Donal F
DF
D000085:Acetates / Q000138:chemical synthesis / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry*; D008872:Microwaves; D008958:Models, Molecular; D008968:Molecular Conformation; D013457:Sulfur Compounds
D000085:Acetates; D007093:Imidazoles; D013457:Sulfur Compounds; C455518:ethyl 2-((2-(3-nitrophenyl)-5-phenyl-1H-imidazol-4-yl)sulfanyl)acetate