TY - JOUR
T1 - The tetrafluoroborate salt of 4-methoxybenzyl N-2-(dimethylamino)ethyl-N- nitrosocarbamate
T2 - Synthesis, crystal structure and DFT calculations
AU - Hedian, Helene
AU - Benin, Vladimir
N1 - Funding Information:
Acknowledgments The authors acknowledge Benjamin E. Kucera and Victor G. Young, Jr., at the X-Ray Crystallographic Laboratory of the Department of Chemistry, University of Minnesota, for the X-ray structure acquisition. V. Benin thanks the University of Dayton Research Council for financial and material support.
Copyright:
Copyright 2012 Elsevier B.V., All rights reserved.
PY - 2011/12
Y1 - 2011/12
N2 - 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.
AB - 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.
KW - DFT
KW - Gauche conformation
KW - Hydrogen bond
KW - N-nitrosocarbamate
KW - Tetrafluoroborate salt
KW - Trialkylammonium salt
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U2 - 10.1007/s10870-011-9991-z
DO - 10.1007/s10870-011-9991-z
M3 - Article
AN - SCOPUS:84855855769
SN - 1074-1542
VL - 41
SP - 1976
EP - 1980
JO - Journal of Chemical Crystallography
JF - Journal of Chemical Crystallography
IS - 12
ER -