. Author manuscript; available in PMC: 2015 Jul 15.

Published in final edited form as: Angew Chem Int Ed Engl. 2012 Feb 3;51(11):2758–2762. doi: 10.1002/anie.201108863

Table 1.

Predicted heterocyclic aryne regioselectivities.

entry	site of attack^a (angle difference)	entry	site of attack^a (angle difference)
1	C5 (4°) / B3LYP C5 (1°) / MP2	2	C5 (7°) / B3LYP C5 (3°) / MP2
	C5 (3°) / B3LYP C5 (<1°) / MP2		C5 (2°) / B3LYP N/A (0°) / MP2
	C6 (17°) / B3LYP C6 (7°) / MP2		C6 (20°) / B3LYP C6 (9°) / MP2

3	C5 (11°) / B3LYP C5 (4°) / MP2	4	C6 (2°) / B3LYP C6 (<1°) / MP2
	C5 (2°) / B3LYP C5 (1°) / MP2		C7 (1°) / B3LYP C7 (1°) / MP2
	C6 (20°) / B3LYP C6 (9°) / MP2		C7 (2°) / B3LYP C7 (3°) / MP2

Predicted site of attack based on the aryne distortion model.