Table 3.

Kinetic vs. thermodynamic study of various neocannabinoids with experimental selectivity ratios and DFT-calculated energies

Entry	Resorcinol 7x	Allylic alcohol 10x	(r.r.), 1 h (3x:6x)a	(r.r.), 24 h (3x:6x)a	Isolated product (±)-3x	% Yield isolated (±)-3x, 24 h	Computational results
							K3/k6 b	ΔG (kcal/mol)c
1	7a	10c	(1:3)	(1:1)	3ac	9%	0.48	1.3
2	7a	10d	(2:5)	(3:4)	3ad	37%	0.24	1.7
3	7a	10e	(1:10)	(3:10)	3ae	16%	0.48	5.9
4	7a	10	(2:3)	(11:1)	3a	47%	1.20	4.8
5	7a	10f	(5:1)	(9:1)	3af	51%	0.34	4.0
6	7	10c	(7:10)	(1:1)	3c	43%	0.67	1.0
7	7	10d	(1:1)	(5:1)	3d	56%	0.85	4.0
8	7	10e	(1:4)	(1:3)	3e	18%	0.51	2.1
9	7	10	(11:10)	(1:0)	3	81%	0.49	1.7
10	7	10f	(27:1)	(25:1)	3f	75%	2.34	1.7
11	7b	10c	(1:0)	(1:0)	3bc	98%	4.52	7.3
12	7b	10d	(1:0)	(1:0)	3bd	98%	8.80	9.3
13	7b	10e	(1:0)	(1:0)	3be	72%	206.01	11.4
14	7b	10	(1:0)	(1:0)	3b	79%	49.72	10.8
15	7b	10f	(1:0)	(1:0)	3bf	56%	117.65	11.9

^aRatio determined by HPLC/ELSD/MS and ¹H NMR analysis.

^b${}^{k^3}∕_{k^6}=e^{{}^{\Delta \Delta G}∕_{kT}}$, where ΔΔG = G(6x^‡) – G(3x^‡), T = 298.15 K, and G(3/6x^‡) is the Boltzmann-averaged free energy.

^cΔG = G(6x) – G(3x), where G(3/6x) is the Boltzmann-averaged free energy.