Philicity and Fugality Scales for Organic Reactions

Table 1

Nucleophilic sites for electron donors and contributions to the regional nucleophilicity index. Adapted with permission from [30].

Species	Nucleophilic sites
HO^−	O	−3.93	0.99	−3.89
HOO^−	O	−3.48	0.74	−2.58
	N1	−5.79	0.49	−2.84
	N2		0.02	−0.12
	N3		0.49	−2.84
CH3O^−	O	−3.99	0.73	−2.91
CF3CH2O^−	O	−4.91	0.75	−3.68
C6H5S^−	S	−5.45	0.62	−3.38
CN^−	C	−6.97	0.39	−2.72
	N		0.61	−4.25
NH2OH	N	−3.72	0.71	−2.64
	O		0.27	−1.00
NH3	N	−4.58	0.97	−4.44
NH2CONHNH2	O	−5.41	0.48	−2.60
H2O	O	−6.65	0.98	−6.52
CF3CH2NH2	N	−4.83	0.78	−3.77
CH3ONH2	O	−3.84	0.68	−2.61
	N		0.23	0.88
CH3CH2CH2S^−	S	−3.46	0.94	−3.25
CH3CH2S^−	S	−3.43	0.95	−3.26
OHCH2CH2S^−	S	−3.15	0.94	−2.96
Piperidine	N	−4.32	0.66	−2.85
Morpholine	N	−4.46	0.49	−2.19
	O		0.13	−0.58

is the central atom.