Solvent mediated reaction of 1-methyl-1H-tetrazoline-5-thione with iodine

被引：8

作者：

Aleshina, Nataliya V. ^{[2
]}

Chernov'yants, Margarita S. ^{[1
]}

Shcherbakov, Igor N. ^{[1
]}

Starikova, Zoya A. ^{[3
]}

机构：

[1] So Fed Univ, Rostov Na Donu 344090, Russia

[2] Russian Acad Sci SSC RAS, So Sci Ctr, Rostov Na Donu 344006, Russia

[3] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

来源：

STRUCTURAL CHEMISTRY | 2011年 / 22卷 / 02期

关键词：

X-ray structure; Heterocyclic compounds; Stability constant; Iodine chemistry; CRYSTAL-STRUCTURES; X-RAY; COMPLEXES; DIIODINE; ADDUCTS; THIONES;

D O I：

10.1007/s11224-010-9710-y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

1-Methyl-1H-tetrazoline-5-thione (1) reacts with iodine in CHCl3 with formation of 1:1 stable sigma-complex (log beta = 3.8 +/- A 0.1 is found by spectrophotometry). In the ethanol solution irreversible oxidation with formation of disulfide product 5,5'-dithiobis(1-methyl-1H-tetrazole) (2) is observed. The structure of (2) was determined by X-ray diffraction. Strong intermolecular interactions with shortened contacts are observed between sulfur atom of disulfide bridge and heterocyclic nitrogen of the neighboring molecule (S center dot center dot center dot N 3.0179(15) ) forming infinite supramolecular chains which are further linked with pi-pi stacking interaction of tetrazole rings (interplane distance is 3.1685(6) angstrom).

引用

页码：313 / 317

页数：5

共 26 条

[1] The Cambridge Structural Database: a quarter of a million crystal structures and rising [J].

Allen, FH .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 2002, 58 (3 PART 1) :380-388

[2]

[Anonymous], 2005, PROGR APEX 2 VERS 2

[3]

[Anonymous], SHELXS97 SHEXL97 PRO

[4]

[Anonymous], 2008, RUSS CHEM REV+

[5] Charge-transfer adducts between donors containing chalcogens (S and Se) and di-iodine: solution studies [J].

Aragoni, MC ;

Arca, M ;

Devillanova, FA ;

Garau, A ;

Isaia, F ;

Lippolis, V ;

Verani, G .

COORDINATION CHEMISTRY REVIEWS, 1999, 184 :271-290

[6] Anti-thyroid drug methimazole:: X-ray characterization of two novel ionic disulfides obtained from its chemical oxidation by I2 [J].

Aragoni, MC ;

Arca, M ;

Demartin, F ;

Devillanova, FA ;

Garau, A ;

Isaia, F ;

Lippolis, V ;

Verani, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (17) :4538-4539

[7] Acidity constants of some tetrazole compounds in various aqueous-organic solvent media [J].

Boraei, AAA .

JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2001, 46 (04) :939-943

[8] Further structural motifs from the reactions of thioamides with diiodine and the interhalogens iodine monobromide and iodine monochloride: an FT-Raman and crystallographic study [J].

Boyle, PD ;

Christie, J ;

Dyer, T ;

Godfrey, SM ;

Howson, IR ;

McArthur, C ;

Omar, B ;

Pritchard, RG ;

Williams, GR .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2000, (18) :3106-3112

[9] The reactions of sulfur and selenium donor molecules with dihalogens and interhalogens [J].

Boyle, PD ;

Godfrey, SM .

COORDINATION CHEMISTRY REVIEWS, 2001, 223 :265-299

[10] 5,5′-Dithiobis(1-phenyl-1H-tetrazole) [J].

Brito, Ivan ;

Cardenas, Alejandro ;

Mundaca, Aldo ;

Villalobos, Hada ;

Lopez-Rodriguez, Matias .

ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 :O2581-O2583

← 1 2 3 →