The tetrafluoroborate salt of 4-methoxybenzyl N-2-(dimethylamino)ethyl-N- nitrosocarbamate: Synthesis, crystal structure and DFT calculations

Helene Hedian, Vladimir Benin

Research output: Contribution to journalArticlepeer-review

Abstract

The tetrafluoroborate salt of 4-methoxybenzyl N-2-(dimethylamino)ethyl-N- nitrosocarbamate was prepared in two steps, via the corresponding carbamate. Its crystal structure is monoclinic, space group P21/c. The unit cell dimensions are: a = 19.499(8) Å , b = 5.877(3) Å , c = 15.757(7) Å , α = 90°, β = 110.019(7)°, γ = 90°, V = 1696.5(12) Å 3, Z = 4. The structure exhibits an unexpected, pseudo-gauche conformation with respect to the C2-C3 bond, due to a stabilizing hydrogen bond between the carbonyl oxygen (O1) and the hydrogen atom at the trialkylammonium center (H3n), with a distance between them of 2.37 Å. DFT calculations on the cation (B3LYP/6-31 + G(d)) confirm that the hydrogen bond stabilized gauche conformation is the global minimum structure.

Original languageEnglish (US)
Pages (from-to)1976-1980
Number of pages5
JournalJournal of Chemical Crystallography
Volume41
Issue number12
DOIs
StatePublished - Dec 1 2011
Externally publishedYes

Keywords

  • DFT
  • Gauche conformation
  • Hydrogen bond
  • N-nitrosocarbamate
  • Tetrafluoroborate salt
  • Trialkylammonium salt

ASJC Scopus subject areas

  • Chemistry(all)
  • Condensed Matter Physics

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