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

被引：8

作者：

Matsulevich, Zhanna, V ^{[1
]}

Lukiyanova, Julia M. ^{[1
]}

Naumov, Vladimir, I ^{[1
]}

Borisova, Galina N. ^{[1
]}

Osmanov, Vladimir K. ^{[1
]}

Borisov, Alexander, V ^{[1
]}

Grishina, Maria M. ^{[2
]}

Khrustalev, Victor N. ^{[2
]}

机构：

[1] RE Alekseev Nizhny Novgorod State Tech Univ, Minin St 24, Nizhnii Novgorod 603950, Russia

[2] Peoples Friendship Univ Russia, RUDN Univ, Inorgan Chem Dept, 6 Miklukho Maklay St, Moscow 117198, Russia

来源：

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS | 2019年 / 75卷

关键词：

bromination; cycloaddition reaction; bis(pyridin-2-yl) diselenide; 2-pyridylselenenyl bromide; cyclopentene; 2,3,3a,9a-tetrahydro-1H-cyclopenta[4,5][1,3]selenazolo[3,2-a]pyri]pyridinium-9 bromide; crystal structure; ALKENES;

D O I：

10.1107/S2056989019004997

中图分类号：

O7 [晶体学];

学科分类号：

0702 ; 070205 ; 0703 ; 080501 ;

摘要：

1H-Pyridine-2-selenenyl dibromide, C5H5NSeBr2, 1, is a product of the bromination of bis(pyridin-2-yl) diselenide in methylene chloride recrystallization from methanol. Compound 1 is essentially zwitterionic: the negative charge resides on the SeBr2 moiety and the positive charge is delocalized over the pyridinium fragment. The C-Se distance of 1.927 (3) angstrom is typical of a single bond. The virtually linear Br-Se-Br moiety of 178.428 (15)degrees has symmetrical geometry, with Se-Br bonds of 2.5761 (4) and 2.5920 (4) angstrom, and is twisted by 63.79 (8)degrees relative to the pyridinium plane. The Se atom forms an intermolecular Se center dot center dot center dot Br contact of 3.4326 (4) angstrom, adopting a distorted square-planar coordination. In the crystal, molecules of 1 are linked by intermolecular N-H center dot center dot center dot Br and C-H center dot center dot center dot Br hydrogen bonds, as well as by non-covalent Se center dot center dot center dot Br interactions, into a three-dimensional framework. (3aSR,(9aRS)-2,3,3a,9a-Tetrahydro-1H-cyclopenta[4,5][1,3]selenazolo[3,2-a]pyridinium-9 bromide, C10H12NSe+center dot Br-, 2, is a product of the cycloaddition reaction of 1 with cyclopentene. Compound 2 is a salt containing a selenazolopyridinium cation and a bromide anion. Both five-membered rings of the cation adopt envelope conformations. The dihedral angle between the basal planes of these rings is 62.45 (11)degrees. The Se atom of the cation forms two additional non-covalent interactions with the bromide anions at distances of 3.2715 (4) and 3.5683 (3) angstrom, attaining a distorted square-planar coordination. In the crystal, the cations and anions of 2 form centrosymmetric dimers by non-covalent Se center dot center dot center dot Br interactions. The dimers are linked by weak C-H center dot center dot center dot Br hydrogen bonds into double layers parallel to (001).

引用

页码：675 / +

页数：11

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