Table 2.

Distortion/Interaction Analysis for the Cycloaddition of Diazoacetamide 1 (R = Me) with Alkynes 3a and 3b and with ONDs 4a and 4b^a

						Δ G ‡ dist				charge (e−) on the dipole (1) in the TSb
dipolarophile		R1	R2	Δ E ‡	Δ G ‡	dipolarophile	dipole (1)	total	Δ G ‡ int	gas-phase	MeOH	Δ
	3a	CO2Me	CF3	9.6	21.5	10.4	14.8	25.2	−3.6	0.25	0.28	0.3
	3b	CO2Me	CO2Me	9.8	22.8	12.7	13.1	25.8	−3.0	0.26	0.28	0.2
	4a	CO2Me	CF3	8.2	22.1	8.1	16.2	24.3	−2.2	0.24	0.25	0.1
	4b	CO2Me	CO2Me	7.8	22.5	6.4	17.7	24.1	−1.6	0.22	0.23	0.1

^aCalculations were performed at the M06-2X/6-31+G(2d,p) level of theory. Energies (kcal/mol) include solvation corrections (MeOH) on gas-phase geometries with the IEFPCM model (radii = UFF);

^bCalculated with natural bond orbital (NBO) analysis.¹⁸