2(s)-amino-6-boronohexanoic acid

2(s)-amino-6-boronohexanoic acid

formula | C_6H_15BNO_5 Hill formula | BC_6H_15NO_5 name | 2(s)-amino-6-boronohexanoic acid IUPAC name | [(5S)-5-azaniumyl-6-hydroxy-6-oxohexyl]-trihydroxyboron mass fractions | B (boron) 5.63% | C (carbon) 37.5% | H (hydrogen) 7.88% | N (nitrogen) 7.3% | O (oxygen) 41.7%

Draw the Lewis structure of 2(s)-amino-6-boronohexanoic acid. Start by drawing the overall structure of the molecule, ignoring potential double and triple bonds: Count the total valence electrons of the boron (n_B, val = 3), carbon (n_C, val = 4), hydrogen (n_H, val = 1), nitrogen (n_N, val = 5), and oxygen (n_O, val = 6) atoms, including the net charge: n_B, val + 6 n_C, val + 15 n_H, val + n_N, val + 5 n_O, val - n_charge = 78 Calculate the number of electrons needed to completely fill the valence shells for boron (n_B, full = 8), carbon (n_C, full = 8), hydrogen (n_H, full = 2), nitrogen (n_N, full = 8), and oxygen (n_O, full = 8). Note that boron has three valence electrons but four bonds, implying that the net charge was given to boron, allowing boron to make the fourth bond and fully fill its valence shell: n_B, full + 6 n_C, full + 15 n_H, full + n_N, full + 5 n_O, full = 134 Subtracting these two numbers shows that 134 - 78 = 56 bonding electrons are needed. Each bond has two electrons, so in addition to the 27 bonds already present in the diagram add 1 bond. To minimize formal charge carbon wants 4 bonds and oxygen wants 2 bonds. Identify the atoms that want additional bonds and the number of electrons remaining on each atom: Fill in the 1 bond by pairing electrons between adjacent highlighted atoms, noting the formal charges of the atoms: Answer: | |

molar mass | 192 g/mol phase | solid (at STP)

predicted LogP hydrophobicity | -2.93 predicted LogS | -1.87

approval status | experimental | small molecule

PubChem CID number | 5287595 PubChem SID number | 7885638 SMILES identifier | NC(CCCC[B-](O)(O)O)C(O)=O InChI identifier | InChI=1/C6H15BNO5/c8-5(6(9)10)3-1-2-4-7(11, 12)13/h5, 11-13H, 1-4, 8H2, (H, 9, 10)/q-1/f/h9H InChI key | BLVGFZFOWWBCCZ-BGGKNDAXCJ