Reactivity of Alkyldibenzothiophenes Using Theoretical Descriptors

Table 1

Electrostatic and geometric properties at the ground state 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]: charge of the sulfur atom, 𝑞_S, the C_4𝑎 atom, 𝑞_C4𝑎, the C_6𝑎 atom, 𝑞_C6𝑎, the dipole moment, 𝜇, the bond distances, 𝑑, and the bond angle, 𝑎. The calculated and experimental data for DBT and thiophene are reported for comparison.

	𝑞S (|𝑒^−|)	𝑞C4𝑎 (|𝑒^−|)	𝑞C6𝑎 (|𝑒^−|)	𝜇 (D)	𝑑S-C4𝑎 (Å)	𝑑S-C6𝑎 (Å)	𝑎C4𝑎-S-C6𝑎 (°)
Thiophene				0.515	1.7329		91.50
Thiophene (exp.)				0.55^c	1.7140^d		92.17^d
DBT	−0.161	0.106		0.793	1.7657		90.96
DBT (exp.)				0.789^a	1.7345^b		91.51^b
3-MDBT	−0.151	0.147	0.063	0.993	1.7660	1.7663	90.97
4-MDBT	−0.124	−0.249	0.227	0.480	1.7689	1.7652	90.99
3,6-DMDBT	−0.120	0.231	−0.228	0.507	1.7654	1.7694	90.99
1,3,6-TMDBT	−0.122	0.296	−0.256	0.772	1.7610	1.7627	90.97
2,3,6-TMDBT	−0.116	0.215	−0.274	0.936	1.7661	17692	90.89
3,7-DMDBT	−0.141	0.104		0.822	1.7666		90.98
1,3,7-TMDBT	−0.129	0.182	0.072	1.093	1.7624	1.7601	90.94
2,3,7-TMDBT	−0.119	0.065	0.075	1.126	1.7672	1.7665	90.87
4,6-DMDBT	−0.148	−0.052		0.024	1.7681		91.03
1,4,6-TMDBT	−0.129	0.022	−0.112	0.334	1.7638	1.7613	91.01
2,4,6-TMDBT	−0.114	−0.054	−0.162	0.441	1.7684	1.7677	90.94
3,4,6-TMDBT	−0.131	−0.029	−0.087	0.558	1.7704	1.7687	91.10
1,4,7-TMDBT	−0.125	−0.080	0.145	0.773	1.7652	1.7587	90.97
2,4,7-TMDBT	−0.126	−0.255	0.204	0.673	1.7695	1.7650	90.90
3,4,7-TMDBT	−0.134	−0.159	0.178	0.460	1.7743	1.7648	91.14

a[26].
^b[27].
^c[28].
^d[29].