Input interpretation
6-chloropurine riboside
Chemical names and formulas
formula | C_10H_11ClN_4O_4 name | 6-chloropurine riboside IUPAC name | (2R, 3R, 4S, 5R)-2-(6-chloro-9-purinyl)-5-(hydroxymethyl)tetrahydrofuran-3, 4-diol alternate names | (2R, 3R, 4S, 5R)-2-(6-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3, 4-diol | (2R, 3R, 4S, 5R)-2-(6-chloropurin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3, 4-diol | (2R, 3R, 4S, 5R)-2-(6-chloropurin-9-yl)-5-methylol-tetrahydrofuran-3, 4-diol | 6-chloropurine-9-β-D-ribofuranoside mass fractions | C (carbon) 41.9% | Cl (chlorine) 12.4% | H (hydrogen) 3.87% | N (nitrogen) 19.5% | O (oxygen) 22.3%
Lewis structure
Draw the Lewis structure of 6-chloropurine riboside. Start by drawing the overall structure of the molecule, ignoring potential double and triple bonds: Count the total valence electrons of the carbon (n_C, val = 4), chlorine (n_Cl, val = 7), hydrogen (n_H, val = 1), nitrogen (n_N, val = 5), and oxygen (n_O, val = 6) atoms: 10 n_C, val + n_Cl, val + 11 n_H, val + 4 n_N, val + 4 n_O, val = 102 Calculate the number of electrons needed to completely fill the valence shells for carbon (n_C, full = 8), chlorine (n_Cl, full = 8), hydrogen (n_H, full = 2), nitrogen (n_N, full = 8), and oxygen (n_O, full = 8): 10 n_C, full + n_Cl, full + 11 n_H, full + 4 n_N, full + 4 n_O, full = 174 Subtracting these two numbers shows that 174 - 102 = 72 bonding electrons are needed. Each bond has two electrons, so in addition to the 32 bonds already present in the diagram add 4 bonds. To minimize formal charge nitrogen wants 3 bonds and carbon wants 4 bonds. Identify the atoms that want additional bonds and the number of electrons remaining on each atom: Fill in the 4 bonds by pairing electrons between adjacent highlighted atoms. Note that the six atom ring is aromatic, so that the single and double bonds may be rearranged: Answer: | |
3D structure
3D structure
Basic properties
molar mass | 286.67 g/mol phase | solid (at STP) melting point | 160 °C
Units
Chemical identifiers
CAS number | 5399-87-1 Beilstein number | 40573 PubChem CID number | 93003 PubChem SID number | 24888323 SMILES identifier | C1=NC2=C(C(=N1)Cl)N=CN2C3C(C(C(O3)CO)O)O InChI identifier | InChI=1/C10H11ClN4O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4, 6-7, 10, 16-18H, 1H2/t4-, 6-, 7-, 10-/m1/s1 MDL number | MFCD00005738