Table 8.

Difference in electronic energies (kcal/mol) between regioisomeric ring opening products (R or S isomer) from reaction of (S)-2a with nucleophile (DLPNO-CCSD(T)/cc-pVTZ).

Nu	Major isomer+	Minor isomer+	ΔE = E(S)-E(R) (kcal/mol)
F	(R)-3a	(S)-4a	6.31
Cl	(R)-5a		4.94
Br	(R)-6a		4.50
I	(R)-7a	(S)-8a	3.81
CN	(S)-9aa	(R)-10aa	2.03
H	(S)-9ab	(R)-10ab	1.52
N3	(R)-9ac	(S)-10ac	5.04
n-PrNH	(S)-9ad	(R)-10ad	5.28
n-PrS	(S)-9ae	(S)-10ae	3.41
OH	(R)-9af	(S)-10af	5.65
CH3O	(R)-9ag	(S)-10ag	3.96
n-PrO	(R)-9ah	(S)-10ah	2.56
Su*	(S)-11		1.67
ONO2	(R)-12		4.70

^*succinimidyl;

⁺isolated