Synthesis and molecular structures of 2-trimethylsilyl-, 2-trimethylgermyl-, and 2-trimethylstannyl-pyridines

Frank Riedmiller, Alexander Jockisch, Hubert Schmidbaur

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

5-Methyl-2-trimethylsilyl-pyridine (1) has recently been prepared via the "in situ" Grignard reaction of 1-bromo-5-methyl-pyridine with magnesium and trimethylchlorosilane in refluxing tetrahydrofuran (thf) and structurally characterized. 2-Trimethylgermyl-(2) and 2-trimethylstannyl-pyridine (3) were now obtained from 2-bromo-pyridine through metallation (with n-BuLi) and treatment of the intermediates with Me3GeBr and Me3SnC1, respectively, in diethylether/ thf at -70°C. The crystal and molecular structure of compound 2 has been determined by low temperature (in situ) single crystal X-ray diffraction methods. There is a significant bending of the Me3Ge substituent towards the nitrogen heteroatom [Ge-C-N = 114.7(2)°]. This phenomenon is known from previous studies of the silicon analogue 1 to be not due to intramolecular (peripheral) Si/Ge←N coordination, but to be rather an intrinsic property of the heteroarene skeleton, as also confirmed by quantum-chemical calculations. Furthermore, there is no evidence for intermolecular coordination in the crystals. Such interactions could also be ruled out for the solution state of 2 and 3 through variable temperature multinuclear NMR investigations.

Original languageEnglish
Pages (from-to)13-17
Number of pages5
JournalZeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume54
Issue number1
DOIs
StatePublished - Jan 1999
Externally publishedYes

Keywords

  • 2-Germyl-pyridine
  • 2-Silyl-pyridine
  • 2-Stannyl-pyridine
  • Molecular structure
  • Pyridine

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