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Article
The Tetrafluoroborate Salt of 4-Methoxybenzyl N-2-(dimethylamino)ethyl-N-nitrosocarbamate: Synthesis, Crystal Structure and DFT Calculations
Journal of Chemical Crystallography
  • Helene Hedian, University of Dayton
  • Vladimir Benin, University of Dayton
Document Type
Article
Publication Date
12-1-2011
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) Å3, 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.
Inclusive pages
1976-1980
ISBN/ISSN
1074-1542
Document Version
Postprint
Comments

The document available for download is the authors' accepted manuscript, posted here in compliance with the publisher's policy on self-archiving.

Some differences may exist between this version and the publisher's version; as such, researchers wishing to quote directly from it are advised to consult the version of record.

Permission documentation is on file.

Publisher
Springer
Peer Reviewed
Yes
Citation Information
Helene Hedian and Vladimir Benin. "The Tetrafluoroborate Salt of 4-Methoxybenzyl N-2-(dimethylamino)ethyl-N-nitrosocarbamate: Synthesis, Crystal Structure and DFT Calculations" Journal of Chemical Crystallography Vol. 41 Iss. 12 (2011)
Available at: http://works.bepress.com/vladimir_benin/14/