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

Research output: Contribution to journal › Article › peer-review

73 Scopus citations

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 Å.

Original language	English
Pages (from-to)	291-297
Number of pages	7
Journal	Crystal Growth and Design
Volume	1
Issue number	4
DOIs	https://doi.org/10.1021/cg015505v
State	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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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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JF - Crystal Growth and Design

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ER -

Hydrogen Bonding with Sulfur

Abstract

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