Reactivity of Alkyldibenzothiophenes Using Theoretical Descriptors

Table 2

Reactivity indexes for DBT and its methyl, dimethyl, and trimethyl derivatives, calculated using the DFT, the B3LYP/6-311+G(d,p) basis set, and the Merz-Kollman population analysis [20]: condensed Fukui functions for electrophilic attacks (𝑓⁻_S), vertical ionization potential (IP), vertical electron affinity (EA), global softness (S), and condensed atomic softness (𝑠⁻_S) at sulfur atom. Calculated and experimental data for thiophene and DBT are reported for comparison.

	𝑓^−S	IP (a.u.)	EA (a.u.)	𝜒 (a.u.)	S (a.u.^−1)	𝑠^−S (a.u.^−1)
Thiophene		0.329	−0.047
Thiophene (exp.)		0.329^b	−0.042^c
DBT	−0.347	0.286	−0.005	0.141	3.426	−1.189
DBT (exp.)		0.291^a
3-MDBT	−0.342	0.283	−0.008	0.137	3.433	−1.175
4-MDBT	−0.311	0.282	−0.007	0.138	3.455	−1.074
3,6-DMDBT	−0.306	0.279	−0.010	0.135	3.462	−1.061
1,3,6-TMDBT	−0.295	0.274	−0.013	0.131	3.486	−1.027
2,3,6-TMDBT	−0.288	0.273	−0.010	0.131	3.526	−1.017
3,7-DMDBT	−0.306	0.280	−0.011	0.134	3.441	−1.164
1,3,7-TMDBT	−0.278	0.274	−0.014	0.130	3.471	−0.965
2,3,7-TMDBT	−0.265	0.273	−0.011	0.131	3.516	−0.932
4,6-DMDBT	−0.305	0.279	−0.009	0.135	3.480	−1.062
1,4,6-TMDBT	−0.271	0.273	−0.011	0.131	3.516	−0.954
2,4,6-TMDBT	−0.279	0.273	−0.009	0.132	3.547	−0.988
3,4,6-TMDBT	−0.342	0.275	−0.011	0.132	3.495	−1.196
1,4,7-TMDBT	−0.273	0.273	−0.013	0.130	3.499	−0.956
2,4,7-TMDBT	−0.306	0.273	−0.010	0.132	3.526	−1.079
3,4,7-TMDBT	−0.262	0.273	−0.012	0.131	3.512	−0.921

a[30].
^b[31].
^c[32].