4-(4'-isopropoxyphenyl)phenylboronic acid

4-(4'-isopropoxyphenyl)phenylboronic acid

molar mass | 256.1 g/mol formula | C_15H_17BO_3 empirical formula | C_15O_3B_H_17 SMILES identifier | CC(C)OC1=CC=C(C=C1)C2=CC=C(C=C2)B(O)O InChI identifier | InChI=1/C15H17BO3/c1-11(2)19-15-9-5-13(6-10-15)12-3-7-14(8-4-12)16(17)18/h3-11, 17-18H, 1-2H3 InChI key | NBOVAIFWBASNLS-UHFFFAOYSA-N

Draw the Lewis structure of 4-(4'-isopropoxyphenyl)phenylboronic 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), and oxygen (n_O, val = 6) atoms: n_B, val + 15 n_C, val + 17 n_H, val + 3 n_O, val = 98 Calculate the number of electrons needed to completely fill the valence shells for boron (n_B, full = 6), carbon (n_C, full = 8), hydrogen (n_H, full = 2), and oxygen (n_O, full = 8): n_B, full + 15 n_C, full + 17 n_H, full + 3 n_O, full = 184 Subtracting these two numbers shows that 184 - 98 = 86 bonding electrons are needed. Each bond has two electrons, so in addition to the 37 bonds already present in the diagram add 6 bonds. To minimize formal charge carbon wants 4 bonds. Identify the atoms that want additional bonds and the number of electrons remaining on each atom: Fill in the 6 bonds by pairing electrons between adjacent highlighted atoms. Note that the six atom rings are aromatic, so that the single and double bonds may be rearranged: Answer: | |

longest chain length | 13 atoms longest straight chain length | 3 atoms longest aliphatic chain length | 3 atoms aromatic atom count | 12 atoms H-bond acceptor count | 2 atoms H-bond donor count | 2 atoms

Find the elemental composition for 4-(4'-isopropoxyphenyl)phenylboronic acid in terms of the atom and mass percents: atom percent = N_i/N_atoms × 100% mass percent = (N_im_i)/m × 100% Plan: • Write the chemical formula and gather atomic masses from the periodic table. • Determine values for N_i, m_i, N_atoms and m using these items. • Finally, compute the percents and check the results. Write the chemical formula: C_15H_17BO_3 Use the chemical formula, C_15H_17BO_3, to count the number of atoms, N_i, for each element and find the total number of atoms, N_atoms: | number of atoms C (carbon) | 15 O (oxygen) | 3 B (boron) | 1 H (hydrogen) | 17 N_atoms = 15 + 3 + 1 + 17 = 36 Divide each N_i by N_atoms to calculate atom fractions. Then use the property that atom fractions must sum to one to check the work: | number of atoms | atom fraction C (carbon) | 15 | 15/36 O (oxygen) | 3 | 3/36 B (boron) | 1 | 1/36 H (hydrogen) | 17 | 17/36 Check: 15/36 + 3/36 + 1/36 + 17/36 = 1 Compute atom percents using the atom fractions: | number of atoms | atom percent C (carbon) | 15 | 15/36 × 100% = 41.7% O (oxygen) | 3 | 3/36 × 100% = 8.33% B (boron) | 1 | 1/36 × 100% = 2.78% H (hydrogen) | 17 | 17/36 × 100% = 47.2% Look up the atomic mass, m_i, in unified atomic mass units, u, for each element in the periodic table: | number of atoms | atom percent | atomic mass/u C (carbon) | 15 | 41.7% | 12.011 O (oxygen) | 3 | 8.33% | 15.999 B (boron) | 1 | 2.78% | 10.81 H (hydrogen) | 17 | 47.2% | 1.008 Multiply N_i by m_i to compute the mass for each element. Then sum those values to compute the molecular mass, m: | number of atoms | atom percent | atomic mass/u | mass/u C (carbon) | 15 | 41.7% | 12.011 | 15 × 12.011 = 180.165 O (oxygen) | 3 | 8.33% | 15.999 | 3 × 15.999 = 47.997 B (boron) | 1 | 2.78% | 10.81 | 1 × 10.81 = 10.81 H (hydrogen) | 17 | 47.2% | 1.008 | 17 × 1.008 = 17.136 m = 180.165 u + 47.997 u + 10.81 u + 17.136 u = 256.108 u Divide the mass for each element by m to calculate mass fractions. Then use the property that mass fractions must sum to one to check the work: | number of atoms | atom percent | mass fraction C (carbon) | 15 | 41.7% | 180.165/256.108 O (oxygen) | 3 | 8.33% | 47.997/256.108 B (boron) | 1 | 2.78% | 10.81/256.108 H (hydrogen) | 17 | 47.2% | 17.136/256.108 Check: 180.165/256.108 + 47.997/256.108 + 10.81/256.108 + 17.136/256.108 = 1 Compute mass percents using the mass fractions: Answer: | | | number of atoms | atom percent | mass percent C (carbon) | 15 | 41.7% | 180.165/256.108 × 100% = 70.35% O (oxygen) | 3 | 8.33% | 47.997/256.108 × 100% = 18.74% B (boron) | 1 | 2.78% | 10.81/256.108 × 100% = 4.221% H (hydrogen) | 17 | 47.2% | 17.136/256.108 × 100% = 6.691%

The first step in finding the oxidation states (or oxidation numbers) in 4-(4'-isopropoxyphenyl)phenylboronic acid is to draw the structure diagram. Next set every oxidation number equal to the atom's formal charge: In 4-(4'-isopropoxyphenyl)phenylboronic acid hydrogen is not bonded to a metal with lower electronegativity, so it will have an oxidation state of +1. Any element bonded to hydrogen gains the bonding electrons, decreasing their oxidation state by 1 for every bond: With hydrogen out of the way, look at the remaining bonds. There are 1 boron-carbon bond, 2 boron-oxygen bonds, 2 carbon-oxygen bonds, and 15 carbon-carbon bonds. For each of these bonds, assign the bonding electrons to the most electronegative element. First examine the boron-carbon bond: element | electronegativity (Pauling scale) | B | 2.04 | C | 2.55 | | | Since carbon is more electronegative than boron, the electrons in this bond will go to carbon. Decrease the oxidation number for carbon (by 1 for single bonds, 2 for double bonds, and 3 for triple bonds), and increase the oxidation number for boron accordingly: Next look at the boron-oxygen bonds: element | electronegativity (Pauling scale) | B | 2.04 | O | 3.44 | | | Since oxygen is more electronegative than boron, the electrons in these bonds will go to oxygen: Next look at the carbon-oxygen bonds: element | electronegativity (Pauling scale) | C | 2.55 | O | 3.44 | | | Since oxygen is more electronegative than carbon, the electrons in these bonds will go to oxygen: Next look at the carbon-carbon bonds: element | electronegativity (Pauling scale) | C | 2.55 | C | 2.55 | | | Since these elements are the same the bonding electrons are shared equally, and there is no change to the oxidation states: Now summarize the results: Answer: | | oxidation state | element | count -3 | C (carbon) | 2 -2 | O (oxygen) | 3 -1 | C (carbon) | 9 0 | C (carbon) | 3 +1 | C (carbon) | 1 | H (hydrogen) | 17 +3 | B (boron) | 1

First draw the structure diagram for 4-(4'-isopropoxyphenyl)phenylboronic acid, and for every non-hydrogen atom, count the σ-bonds. Note that double and triple bonds consist of one σ-bond together with one or two π-bonds: Identify those atoms with lone pairs: Find the steric number by adding the lone pair count to the number of σ-bonds: Consult the following chart to determine the hybridization from the steric number: steric number | hybridization 2 | sp 3 | sp^2 4 | sp^3 5 | dsp^3 6 | d^2sp^3 7 | d^3sp^3 Assign the provisional hybridization based on the table: Next identify any sp^3 atoms with lone pair electrons which can participate in a conjugated π-bond system. These atoms can lower their energy by placing a lone pair in a unhybridized p orbital to maximize overlap with the neighboring π-bonds. Note that halogens and elements from the third period and below do not engage in bond conjugation, except in the case of aromaticity: Adjust the provisional hybridizations to arrive at the result: Answer: | |

vertex count | 36 edge count | 37 Schultz index | 14670 Wiener index | 3732 Hosoya index | 7.061×10^6 Balaban index | 2.412