Roger E. Cramer, Christopher A. Waddling, Cy H. Fujimoto, David W. Smith and K. Emilei Kim
Reflux of thiamin
[3-(4-amino-2-methylpyrimidin-5-ylmethyl)-5-(2-hydroxyethyl)-4-methylth
iazolium] mononitrate in methanol for 2 h, followed by recrystallization
from methanol, produced single crystals of
[L][NO3]6·16H2O
{L =
5,12,19,26,33,40-hexaamino-3,10,17,24,31,38-hexamethyl[1.6
](1,5)pyrimidiniophane, or 24-pyrimidinium crown 6}. The compound
crystallizes in the rhombohedral space group
R,
a = b = c
= 14.131(11) Å,
α = β = γ =
115.26(5)°, Z = 1,
R = 0.0469, 1352 independent reflections with
F > 2.0σ(F
). Reflux of
[L][NO3]6·16H2O in
methanol–water (3∶2) for 182 h produced single crystals of
the nitric acid salt of 4-amino-5-methoxymethyl-2-methylpyrimidine. The
compound crystallizes in the triclinic space group P
,
a = 9.116(6),
b = 9.452(5),
c = 12.742(8) Å,
α = 101.14(5), β = 107.13(5),
γ = 93.27(5)°, Z = 4,
R = 0.0644, 2690 independent reflections with
F > 2.0σ(F
). The nitric
acid salt of 4-amino-2-methylpyrimidine-5-methanol has been isolated and
identified by 1H NMR spectroscopy from the thermal
decomposition reaction of
[L][NO3]6·16H2O in water. The
alcohol has also been observed by 1H NMR spectroscopy in the
decomposition of [L]6+ in aqueous solutions at room
temperature.