The molecular structure of o-carboxyphenyl methyl sulphoxide and o-carboxyphenyl methyl selenium oxide

Abstract

o-Carboxyphenyl methyl sulphoxide and o-carboxyphenyl methyl selenium oxide are monoclinic (P2Jc) with cell dimensions a= 8-979, b = 11"660, c= 9.554 A, t= 123.62 ° and a= 8.948, b = 11.445, c= 9.583 A, t= 122.03 ° respectively. Although the two compounds show very similar atomic positions the molecular structures are essentially different. The hydroxyl hydrogen atom of the carboxyl group of the sulphur compound corresponds to the hydrogen atom attached to the selenium oxide oxygen, and there are several structural indications that there is ring closure by a Se-O bond. However, this bond is 2.378 A which is 34 % longer than a normal Se-O covalent bond. Both molecules are mainly planar except for the methyl group, which projects from the benzene ring plane. The molecules are linked together by a hydrogen bond from the hydroxyl oxygen to the oxygen attached to sulphur and selenium respectively in the adjacent molecule.

Synthesis, Structure and Antioxidant Activity of Cyclohexene-Fused Selenuranes and Related Derivatives

“…The geometry around the central atom is distorted trigonal bipyramidal in which two Se–O bonds occupy the axial positions, two Se–C bonds and the lone pair occupy the equatorial positions. The Se–O bond length of 1.971(1) Å is slightly elongated compared to the covalent Se–O bond length (1.83 Å) and in good agreement with reported Se–O bond distance of 1.968(1) Å for 3,3′-spirobis(3-selenanaphthalide) [44] and significantly longer than that observed in 2-carboxylphenylmethyl selenoxide [45], {Se–O (1.774 Å)}. The O1A–Se–O1A bond angle is 172.99° which is deviated from the linear arrangement of 180°.…”

Synthesis and structural characterization of pincer type bicyclic diacyloxy- and diazaselenuranes

“…The O(3)-Se-O(2) angle is 163.86 (7) • , which is significantly smaller than that observed for 1 (172.4(3) • ), the monocyclic selenurane 42 (169.9 (2) • ) 28 and spiroselenurane 6 (172.99 • ). 11 However, it is in close agreement with the corresponding angles 163.4(2) • and 165.8(2) • , observed for the 1,2-oxaselenetane 5 8a and spirocyclic selenurane 43, 29 respectively.…”

Experimental and theoretical evidence for cyclic selenurane formation during selenomethionine oxidation

“…The Se-O bond to the carboxylic acid is slightly shorter than that in the crystal structure of 4b (2.378 A ˚). 24 The theoretical results suggest that the resonances at 703 and 716 ppm are Se-N selenuranes, but cannot conclusively eliminate the Se-O species. Experimental confirmation of the theoretical results was sought by derivatizing SeMet to block interactions between Se and the amino acid groups.…”