Hydrogen bonding with sulfur

被引：69

作者：

Krepps, MK ^{[1
]}

Parkin, S ^{[1
]}

Atwood, DA ^{[1
]}

机构：

[1] Univ Kentucky, Dept Chem, Lexington, KY 40506 USA

来源：

CRYSTAL GROWTH & DESIGN | 2001年 / 1卷 / 04期

关键词：

D O I：

10.1021/cg015505v

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The hydrogen-bonding capabilities of the sulfur-containing molecule trimercaptotriazine (TMT) was explored using various amines. The amines were chosen to observe the effect of varying base strength on the resulting hydrogen-bonded structures. The specific compounds [pyrrolidineH](+)(2)[HTMT]2-.THF (1), [triethylamineH](+)[H2TMT](-).THF (2), [propylenediamineH(2)](2+)[HTMT](2-) (3), [ethylenediamineH](+)2[HTMT](2-) (4), and [pyridineH](+)[H2TMT](-)(H3TMT.2(pyridine)) (5) were characterized by melting point, elemental analysis, infrared spectroscopy, and X-ray crystallography. It was found that the TMT molecule is readily deprotonated by all of the amines and that the subsequent ammonium hydrogens formed several types of hydrogen bonds. Importantly, these bonds were observed to form with the sulfur atoms of the TMT, with S...N distances of 3.3-3.5 Angstrom.

引用

收藏

页码：291 / 297

页数：7

相关论文

共 23 条

[1]

ADMAN E, 1975, P NATL ACAD SCI USA, V72, P4854, DOI 10.1073/pnas.72.12.4854

[2] Resonance-induced hydrogen bonding at sulfur acceptors in R1R2C=C and R1CS2- systems [J].

Allen, FH ;

Bird, CM ;

Rowland, RS ;

Raithby, PR .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1997, 53 :680-695

[3] Transition metal complexes of 2,4,6-trimercapto-1,3,5-triazine (TMT): potential precursors to nanoparticulate metal sulfides [J].

Bailey, JR ;

Hatfield, MJ ;

Henke, KR ;

Krepps, MK ;

Morris, JL ;

Otieno, T ;

Simonetti, KD ;

Wall, EA ;

Atwood, DA .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 623 (1-2) :185-190

[4] CRYSTAL-STRUCTURE AND THERMIC BEHAVIOR OF ADDITION-COMPOUNDS OF TRITHIOCYANURIC ACID WITH TETRAHYDROFURAN AND 1,4-DIOXANE [J].

BELAJ, F ;

TRIPOLT, R ;

NACHBAUR, E .

MONATSHEFTE FUR CHEMIE, 1990, 121 (2-3) :99-108

[5] ELECTRON-DISTRIBUTION IN 1-ORGANO-1H-TETRAZOLE-5-THIOLS - CRYSTAL AND MOLECULAR-STRUCTURE OF 1-METHYL-1H-TETRAZOLE-5-THIOL AND ITS POTASSIUM(18-CROWN-6) SALT [J].

CEAOLIVARES, R ;

JIMENEZSANDOVAL, O ;

HERNANDEZORTEGA, S ;

SANCHEZ, M ;

TOSCANO, RA ;

HAIDUC, I .

HETEROATOM CHEMISTRY, 1995, 6 (01) :89-97

[6] METAL-COMPLEXES OF 1,3,5-TRIAZINE-2,4,6-TRITHIOL [J].

CHUDY, JC ;

DALZIEL, JAW .

JOURNAL OF INORGANIC & NUCLEAR CHEMISTRY, 1975, 37 (12) :2459-2461

[7] The N-H•S hydrogen bond in (TACN)2Fe2S6 (TACN = triazacyclononane) and in model systems involving the persulfido moiety:: An ab initio and DFT study [J].

François, S ;

Rohmer, MM ;

Bénard, M ;

Moreland, AC ;

Rauchfuss, TB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) :12743-12750

[8]

HAHN T, INT TABLES CRYSTALLO, VA

[9] CRYSTAL ENGINEERING OF HYDROGEN-BONDED CO-CRYSTALS BETWEEN CYANURIC ACID AND DIAMIDE MOLECULES - INVESTIGATIONS ON THE FORMATION AND STRUCTURE OF CO-CRYSTALS CONTAINING CYANURIC ACID AND OXALYL DIHYDRAZIDE [J].

HARRIS, KDM ;

STAINTON, NM ;

CALLAN, AM ;

HOWIE, RA .

JOURNAL OF MATERIALS CHEMISTRY, 1993, 3 (09) :947-952

[10] Group 2 complexes of 2,4,6-trimercaptotriazine (TMT) [J].

Henke, K ;

Atwood, DA .

INORGANIC CHEMISTRY, 1998, 37 (02) :224-227