Host-guest-like thiamine-anion complexation in thiaminium bis(tetrafluoroborate).
In the title compound, 3-[(4-amino-2-methyl-5-pyrimidin-1-io)methyl]-5-(2-hydroxyethyl)-4-methylthiazolium(2+) bis(tetrafluoroborate), C(12)H(18)N(4)OS(2+).2BF(4)(-), the divalent thiamine cation (in the F conformation) is associated with BF(4)(-) anions via two characteristic bridging interactions between the thiazolium and pyrimidinium rings, i.e. C-H...BF(4)(-)...pyrimidinium and N-H...BF(4)(-)...thiazolium interactions. Thiamine molecules are linked by N-H...O hydrogen bonds to form a helical chain structure.
Hu
N H
NH
Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, People's Republic of China. hunh@ciac.jl.cn
Aoki
K
K
Adeyemo
A O
AO
Williams
G N
GN
D000838:Anions; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D015394:Molecular Structure; D011743:Pyrimidines / Q000737:chemistry*; D013831:Thiamine / Q000031:analogs & derivatives* / Q000737:chemistry; D013844:Thiazoles / Q000737:chemistry*
C438625:3-((4-amino-2-methyl-5-pyrimidin-1-io)methyl)-5-(2-hydroxyethyl)-4-methylthiazolium(2+) bis(tetrafluoroborate); D000838:Anions; D011743:Pyrimidines; D013844:Thiazoles; D013831:Thiamine