Hydrogen Bonding with Sulfur

Matthew K. Krepps; Sean Parkin; David A. Atwood

doi:10.1021/cg015505v

Hydrogen Bonding with Sulfur

Matthew K. Krepps, Sean Parkin, David A. Atwood

Chemistry

Producción científica: Article › revisión exhaustiva

74 Citas (Scopus)

Resumen

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), [propylenediamineH₂]²⁺[HTMT]^2- (3), [ethylenediamineH]⁺₂[HTMT]^2- (4), and [pyridmeH]⁺[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 Å.

Idioma original	English
Páginas (desde-hasta)	291-297
Número de páginas	7
Publicación	Crystal Growth and Design
Volumen	1
N.º	4
DOI	https://doi.org/10.1021/cg015505v
Estado	Published - jul 2001

ASJC Scopus subject areas

General Chemistry
General Materials Science
Condensed Matter Physics

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title = "Hydrogen Bonding with Sulfur",

abstract = "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), [propylenediamineH2]2+[HTMT]2- (3), [ethylenediamineH]+2[HTMT]2- (4), and [pyridmeH]+[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 {\AA}.",

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doi = "10.1021/cg015505v",

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T1 - Hydrogen Bonding with Sulfur

AU - Krepps, Matthew K.

AU - Parkin, Sean

AU - Atwood, David A.

PY - 2001/7

Y1 - 2001/7

N2 - 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), [propylenediamineH2]2+[HTMT]2- (3), [ethylenediamineH]+2[HTMT]2- (4), and [pyridmeH]+[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 Å.

AB - 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), [propylenediamineH2]2+[HTMT]2- (3), [ethylenediamineH]+2[HTMT]2- (4), and [pyridmeH]+[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 Å.

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U2 - 10.1021/cg015505v

DO - 10.1021/cg015505v

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JO - Crystal Growth and Design

JF - Crystal Growth and Design

IS - 4

ER -

Hydrogen Bonding with Sulfur

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