Hydrogen Bonding with Sulfur

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

Research output: Contribution to journalArticlepeer-review

69 Scopus citations


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 languageEnglish
Pages (from-to)291-297
Number of pages7
JournalCrystal Growth and Design
Issue number4
StatePublished - Jul 2001

ASJC Scopus subject areas

  • General Chemistry
  • General Materials Science
  • Condensed Matter Physics


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