. 2022 Mar 4;7(10):8199–8208. doi: 10.1021/acsomega.1c07176

Table 2. Barrier Heights (in kcal·mol^–1) for the Identity Exchange EAS Reaction of Monosubstituted Benzenes with Hydrogen Fluoride and Hirshfeld Charges (in Electrons) Are Given for meta and para Carbons from M06-2X/aug-cc-pVDZ Computations^a.

R	isomer	q(Hirsh)	barrier height	R	isomer	q(Hirsh)	barrier height
H		–0.0498	28.41	tBu	m-	–0.0514	27.63
Cl	m-	–0.0414	31.57		p-	–0.0554	25.34
	p-	–0.0488	27.35	CCl₃	m-	–0.0417	31.10
Et	m-	–0.0506	27.79		p-	–0.0387	31.89
	p-	–0.0554	25.23	CF₃	m-	–0.0399	32.23
F	m-	–0.0419	31.64		p-	–0.0368	33.16
	p-	–0.0560	25.38	CHO	m-	–0.0449	31.16
Me	m-	–0.0506	28.45		p-	–0.0337	32.96
	p-	–0.0558	24.59	CN	m-	–0.0380	33.47
NH₂	m-	–0.0501	30.29		p-	–0.0326	33.94
	p-	–0.0717	11.09	COF	m-	–0.0408	33.00
NMe₂	m-	–0.0525	29.83		p-	–0.0292	34.90
	p-	–0.0748	12.18	NH₃⁺	m-	–0.0082	53.02
OH	m-	–0.0474	29.56		p-	–0.0048	54.92
	p-	–0.0658	16.69	NO₂	m-	–0.0365	34.29
Pr	m-	–0.0508	28.49		p-	–0.0296	35.37
	p-	–0.0554	24.69	NO	m-	–0.0420	31.85
					p-	–0.0298	34.08
				SO₃H	m-	–0.0356	33.68
					p-	–0.0296	35.33

Adapted from ref (16), with permission from the author.

Table 2. Barrier Heights (in kcal·mol–1) for the Identity Exchange EAS Reaction of Monosubstituted Benzenes with Hydrogen Fluoride and Hirshfeld Charges (in Electrons) Are Given for meta and para Carbons from M06-2X/aug-cc-pVDZ Computationsa.