Table of Stereoelectronic Parameters

Stereoelectronic parameters of EZ3 ligands and groups (E = P, N, As, Sb; Si, Ge, Sn). Ligands are listed in order of increasing cone angle. The ligands are linked to compilations of analyses that include the specific ligand.

 

EZ3

E = P

E = N E = Si E = Sn E = As E = Sb

cd (a)

q (b)

Ear (c)

pp (d)

PH3

N Si Sn As Sb

17

87

0

3.7

PH2F

N Si Sn As Sb

22.3

93

0

6.9

PH2(OMe)

N Si Sn As Sb

17.3

87

0.3

3.4

PH2Me

N Si Sn As Sb

14.2

97

0

2.5

PF2H N Si Sn As Sb

27.7

98

0

10.0

PH2Cl

N Si Sn As Sb

25.3

99

1.4

4.2

          100    

PH(OMe)2

N Si Sn As Sb

17.6

100

0.3

3.1

P(OCH2)3CH

N Si Sn As Sb

 

101

 

 

P(OCH2)3CMe

N Si Sn As Sb

20.2

101

0.2

5

P(OCH2)3CEt

N Si Sn As Sb

20.2

101

0.2

5

PEtH2 N Si Sn As Sb
13.4
102
0
2.5
PH2(Hex) N Si Sn As Sb
13
103
0
2.5

PH2(Oct)

N Si Sn As Sb

13

103

0

2.5

PH2Pr

N Si Sn As Sb

13.1

103

0

2.5

PH2Bu

N Si Sn As Sb

13.1

103

0

2.5

PH(OEt)2 N Si Sn As Sb

16.2

102

0.7

3.2

PH(OBu)2

N Si Sn As Sb

16.3

102

0.9

3.2

P(CF3)H2

N Si Sn As Sb

22.3

104

0

6.2

PF3

N Si Sn As Sb

33

104

0

13.2

PH2(i-Bu)

N Si Sn As Sb

13.2

106

0

2.5

P(p-MeOC6H4)H2

N

Si   As Sb

14.8

106

1

2.5

P(p-MeC6H4)H2

N Si   As Sb

15.2

106

1

2.5

PH2Ph

N Si   As Sb

15.8

106

1

2.5

P(p-FC6H4)H2

N Si Sn As Sb

16.6

106

1

2.5

P(p-ClC6H4)H2

N

Si   As Sb

16.9

106

1

2.5

P(p-O2NC6H4)H2

N Si   As Sb

106

0

2.5

P(p-CF3C6H4)H2

N

Si   As Sb

18.2

106

1

2.5

PF(OMe)2

N Si Sn As Sb

22.9

106

0.7

6.3

PHMe2

N Si Sn As Sb

11.4

107

0

1.2

P(OMe)3

N Si   As Sb

17.9

107

1

2.8

PF(OEt)2

N Si Sn As Sb

21.5

107

0.8

6.3

P(OEt)(OMe)2

N Si Sn As Sb

17.2

108

1.0

2.8

P(OMe)2(OPr)

N Si Sn As Sb

17.2

108

1.0

28

P(OEt)3

N Si   As Sb

15.8

109

1.1

2.9

P(OPr)3 N Si   As Sb

15.9

109

1.1

2.9

PF2Me

N Si   As Sb

24.9

109

0

8.8

        110    

P(OBu)3

N Si   As Sb

15.9

110

1.3

2.7

P(OPr)3

N Si   As Sb

15.9

110

1.3

2.7

P(OCH2CH2Cl)3

N Si   As Sb

20.4

110

0.4

3.6

P(OCH2CH2C6F13)3

N Si   As Sb

22

110

0

5

PClHMe N Si   As Sb

22.5

110

1.4

3.0

P(i-Pr)H2

N Si   As Sb

12.5

111

0

2.5

PMe(OMe)2

N Si   As Sb
14.8

111

0.7

1.9

PClF2

N Si   As Sb
36

111

1.4

10.6

PMe(OEt)2

N Si   As Sb

13.4

112

0.7

1.9

PCl2H N Si   As Sb
33.7

 

112

2.7

4.8

PFMe2

N Si   As Sb

16.7

113

0

4.4

PEtF2

N Si Sn As Sb

24.1

113

0

8.8

PCl(OMe)2 N Si   As Sb

25.9

113

2.0

3.6

PF2Vi N Si   As Sb

26.5

113

*

8.8

PBrF2 N Si   As Sb
35.2
113
   

PMe2(OMe)

N Si   As Sb

11.7

114

0.3

0.9

PHPh(OEt)

N Si Sn As Sb

15.4

114

1.3

0.9

PHMe(CF3)

N Si Sn As Sb

19.5

114

0

4.9

P(OMe)2(OPh)

N Si Sn As Sb

19.8

114

1.1

3.2

P(OMe)2(O-p-ClC6H4)

N Si Sn As Sb

21.0

114

1.1

3.2

PH(OPh)2

N Si Sn As Sb

21.4

114

0.9

4.0

PCl(OEt)2 N Si   As Sb

24.5

114

2.1

3.7

PMe2(OEt)

N Si   As Sb

11

115

0.4

1

PCyH2

N Si   As Sb

11.8

115

0

2.5

P(OEt)2(OPh)

N Si Sn As Sb

18.4

115

1.2

3.3

PCl(OPr)2 N Si   As Sb

24.6

115

2.2

3.6

PF2(CF3)

N Si Sn As Sb

33.0

115

0

12.5

PClMe(OMe)

N Si Sn As Sb

22.8

116

1.7

 

2.7

PEt2H N Si   As Sb
9.9

117

0

1.2

PEt(OEt)2

N Si Sn As Sb

12.6

117

0.7

1.8

PHMePh N Si   As Sb
12.9
117
1
1.2

P(CH2CH2CN)2H

N Si   As Sb

17.0

117

0

2

PClMe(OEt)

N Si Sn As Sb

22.1

117

1.7

2.7

PCl2F

N Si Sn As Sb

39

117

2.8

7.9

PMe3

N Si Sn As Sb

8.55

118

0

0

PBu(OEt)2

N Si Sn As Sb

12.3

118

0.7

1.8

PF2Ph

N Si   As Sb

26.4

118

1

4.4

PCl2(OMe)

N Si Sn As Sb

34.0

118

3.2

4.5

P(t-Bu)H2

N Si   As Sb

11.3

119

0

2.5

PBu(OBu)2

N Si Sn As Sb

12.4

119

0.7

1.8

P(C6F5)H2

N Si   As Sb

22.9

119

1.5

2.5

PClMePh N Si Sn As Sb

24.1

119

2.3

1.8

PCl2(OPr)

N Si Sn As Sb

33.3

119

3.2

4.4

PCl2(OEt)

N Si Sn As Sb

33.3

119

3.1

4.5

PCl2(OBu)

N Si Sn As Sb

33.3

119

3.2

4.4

        120    
P(Hex)2H N Si   As Sb
9
120
0
1.2
PH(pentyl)2 N Si   As Sb        

P(Oct)2H

N Si   As Sb

9

120

0

1.2

PBu2H

N Si   As Sb

9.2

120

0

1.2

P[O-(i-Bu)]3

N Si   As Sb

15.5

120

1.4

3

P(OMe)2Ph

N Si   As Sb

16.4

120

1.7

1.9

PClMe2

N Si   As Sb

19.7

120

1.4

1.8

P(CF3)2H

N Si   As Sb

27.7

120

0

8.6

P(OEt)2Ph

N Si   As Sb

15

121

1.7

1.9

P(OEt)2(p-ClC6H4)

N Si Sn As Sb

16.1

121

1.6

1.9

P(OMe)(OPh)2

N Si Sn As Sb
21.7

 

121

1.2

3.7

P(OMe)(O-p-ClC6H4)2

N Si Sn As Sb

24.1

121

1.2

3.6

PMe2(p-Me2NC6H4) N Si   As Sb

7.5

122

1

0

PMe2(p-MeOC6H4) N Si   As Sb
9.2
122
1
0
PMe2(p-MeC6H4) N Si   As Sb
9.5
122
1
0

PPhMe2

N Si   As Sb

10.5

122

1

0

PMe2(p-ClC6H4) N Si   As Sb
11.3
122
1
0
PPhMeF N Si   As Sb
18.3
122
1
4.4
PBrMe2 N Si Sn As Sb
18.9
122
   

P(OEt)(OPh)2

N Si Sn As Sb

21

122

1.2

3.7

PCl2Me

N Si Sn As Sb

30.9

122

2.7

3.5

PBr2F N Si Sn As Sb
37.3
122
PMe2(p-EtOC(O)C6H4) N Si Sn As Sb
122
PMe2(p-NCC6H4) N Si Sn As Sb
122
PMe2(p-NO2C6H4) N Si   As Sb
122
PMe2Pr N Si   As Sb
7.5
123
0
0

PMe2Et

N Si   As Sb

7.8

123

0

0

PMe2Vi N Si   As Sb

10.3

123

*

0

PMe2(CH2CH2CN)

N Si   As Sb

11.4

123

0

0.4

PMe2(hexyl) N Si Sn As Sb
7.4
124
0
0

P(i-Bu)2H

N Si   As Sb

9.5

124

0

1.2

P(CH2CH2CF3)Me2 N Si   As Sb
10.2
124
0
0.8

P(CF3)Me2

N Si Sn As Sb

16.7

124

0

3.7

PCl3

N Si Sn As Sb

42

124

4.1

5.3

PMe(OPh)2

N Si   As Sb

18.6

125

.8

2.8

PCl2(OPh)

N Si Sn As Sb

35.9

125

3.2

4.9

PH(p-MeC6H4)2 N Si   As Sb

13.3

126

2

1.2

PPh2H

N Si   As Sb

14.5

126

2

1.2

PF(CF3)2

N Si   As Sb

33

126

0

11.8

PMeEt2

N Si   As Sb

7.1

127

0

0

PBu2(OBu)

N Si Sn As Sb

8.8

127

0.4

0.9

PCl(OPh)2

N Si Sn As Sb

29.7

127

2.3

4.5

PBr2Me

N Si Sn As Sb

29.8

127

2.7

3.5

PPrCl2

N Si   As Sb

29.8

127

2.7

3.5

PCl2Et

N Si   As Sb

30.1

127

1.4

3.6

PCl2Vi N Si   As Sb

32.6

127

*

3.5

PMe2(m-ClC6H4)

N Si Sn As Sb

12.2

128

1

0

PMe(CH2CH2CN)2

N Si   As Sb

14.2

128

0

0.8

P(O-p-MeC6H4)3

N Si   As Sb

22.4

128

1.4

4.1

P(O-p-MeOC6H4)3

N Si   As Sb

22.5

128

1.4

3.8

PCl(O-i-Pr)2 N Si   As Sb

22.9

128

2.2

3.6

P(OC6H5)3

N Si   As Sb

23.6

128

1.3

4.1

P(O-p-ClC6H4)3

N Si   As Sb

27.2

128

1.3

4

PBuCl2

N Si Sn As Sb

29.8

128

2.8

3.6

P(O-p-NCC6H4)3

N Si   As Sb

31.7

128

1

3.7

P(CF3)Cl2

N Si   As Sb

39

128

2.7

7.2

PMePr2 N Si   As Sb
6.5
129
0
0
PPhMeCl N Si   As Sb
21.3
129
2.3
1.8

PEt(OPh)2

N Si   As Sb

17.8

129

0.8

 

2.8

PClEt2

N Si Sn As Sb

18

129

1.4

1.8

       
130
   
PMe(pentyl)2 N Si   As Sb
6.2
130
0
0
PMe(hexyl)2 N Si   As Sb
6.2
130
0
0
PMe(heptyl)2 N Si   As Sb
6.2
130
0
0
PMe(octyl)2 N Si   As Sb
6.20
130
0
0
PMe(nonyl)2 N Si   As Sb
6.20
130
0
0
PMe(decyl)2 N Si   As Sb
6.20
130
0
0
PBu2Me N Si   As Sb
6.4
130
0
0
PMe(CH2CH2CF3)2 N Si   As Sb
11.8
130
0
0.8

P(O-i-Pr)3

N Si   As Sb

13.4

130

1.3

2.9

P(t-Bu)F2

N Si   As Sb

22

130

0

8.8

P(OCH2CF3)3

N Si   As Sb

 

 

 

 

PFPh2 N Si   As Sb
19.8
131
2.0
4.4

P(CF3)2Me

N Si   As Sb

24.9

131

0

7.4

P(p-MeOC6H4)Cl2

N Si   As Sb

31.5

131

3.7

3.5

PPhCl2

N Si Sn As Sb

32.4

131

3.7

3.5

PBr3 N Si Sn As Sb
39.5
131
   

PEt3

N Si Sn As Sb

6.3

132

0

0

PMe2(i-Pr)

N Si   As Sb

6.9

132

0

0

PEt2(CH2CH2CN)

N Si   As Sb

9.9

132

0

0.4

PEt(CH2CH2CN)2

N Si   As Sb

13.4

132

0

0.8

P(OMe)Ph2

N Si   As Sb

14.8

132

2.3

0.9

P(CH2CH2CN)3

N Si   As Sb

17

132

0

1.2

PBu2Cl

N Si Sn As Sb

17.5

132

1.4

1.8

P(octyl)(CH2CH2CN)2

N Si   As Sb

13

133

0

0.8

P(OEt)Ph2

N Si   As Sb

14.1

133

2.4

1

PPh2OCH2CH2C6F13

N Si      

 

P(C6F5)(OMe)2 N Si   As Sb
23.5
133
2
1.8

P(CF3)2Cl

N Si   As Sb

36

133

1.4

9.2

PEt2Vi N Si   As Sb
8.8
132
0
PEtVi2 N Si   As Sb
11.2
132
0
PVi3 N Si   As Sb
13.65
132
0
PEtPr2 N Si   As Sb
5.7
133
0
0

PPr3

N Si   As Sb

5.4

134

0

0

PPr3 N Si Sn As Sb
5.4
134
0
0

PBu(CH2CH2CN)2

N Si   As Sb

13.1

134

0

0.8

PPh(OPh)2

N Si   As Sb

20.2

134

1.9

2.7

PBr(CF3)2

N Si Sn As Sb

35.2

134

 

 

PBu2Pr N Si   As Sb

5.3

135

0

0

PEt(hexyl)2 N Si   As Sb
5.4
135
0
0
PEt(heptyl)2 N Si   As Sb
5.4
135
0
0
PEt(nonyl)2 N Si   As Sb
5.4
135
0
0
PEt(octyl)2 N Si   As Sb
5.4
135
0
0
PEt(decyl)2 N Si   As Sb
5.4
135
0
0
PEtBu2 N Si   As Sb
5.6
135
0
0

PCyMe2

N Si   As Sb

6.2

135

0

0

PMe(i-Bu)2

N Si   As Sb

6.7

135

0

0

PBu2Vi

N Si   As Sb

8.1

135

0

P(Oct)2(CH2CH2CN)

N Si   As Sb

9

135

0

0.4

PBu2(CH2CH2CN)

N Si   As Sb

9.2

135

0

0.4

PEt(CH2CH2CF3)2

N Si   As Sb

11

135

0

1.4

PEt(CF3)2

N Si   As Sb

24.1

135

0

7.4

P(C16H33)3

N Si Sn As Sb

5

136

0

0

P(decyl)3

N Si Sn As Sb

5

136

0

0

P(dodecyl)3

N Si Sn As Sb

5

136

0

0

P(Hexyl)3 N Si   As Sb
5
136
0
0
P(Heptyl)3 N Si   As Sb
5
136
0
0

P(nonyl)3

N Si Sn As Sb

5

136

0

0

P(Pentyl)3

N Si   As Sb

5

136

0

0

POct3

N Si   As Sb

5

136

0

0

PBu3

N Si Sn As Sb

5.25

136

0

0

PMe(p-MeNC6H4)2

N Si Sn As Sb

6.35

136

2

0

PEt2(p-MeOC6H4) N Si   As Sb

7.7

136

1

0

PEt2(p-MeC6H4) N Si   As Sb

8

136

1

0

PH(i-Pr)2 N Si   As Sb
8
136
0
1.2

PMe(p-MeC6H4)(p-Me2NC6H4)

N Si Sn As Sb

8.4

136

2

0

PPhEt2

N Si   As Sb

8.6

136

1.1

0

PEt2(p-ClC6H4) N Si   As Sb

9.8

136

1

0

PMe(p-MeOC6H4)2

N Si Sn As Sb

9.9

136

2

0

PMe(p-MeC6H4)2

N Si   As Sb

10.5

136

2

0

PMePh(p-MeOC6H4)

N Si Sn As Sb

10.8

136

2

0

PMePh(p-MeC6H4)

N Si Sn As Sb

10.9

136

2

0

PPh2Me

N Si Sn As Sb

12.6

136

2.2

0

PMePh(p-ClC6H4)

N Si Sn As Sb

12.9

136

2

0

PPh(CH2CH2CN)2

N Si   As Sb

15.8

136

1

0.8

P(CH2CH2C6F13)3

N Si   As Sb

13.4

136

0

2.3

P(CH2CH2Rf8)3

N Si   As Sb

13.4

136

0

2.3

P(CH2)3Rf8)3

N Si   As Sb

 

136

P(CH2)4Rf8)3

N Si   As Sb

 

136

P(CH2)5Rf8)3

N Si   As Sb

 

136

P(CH2CH2CF3)3 N Si   As Sb
13.,4
136
0
2.3
PVi3 N Si   As Sb
13.,65
136
0
0

PMe(p-ClC6H4)2

N Si   As Sb

14.1

136

2

0

PBr2Ph N Si Sn As Sb
30.8
136

P(CF3)3

N Si   As Sb

33

136

0

11.1

PMe(p-MeOC(O)C6H4)2

N Si Sn As Sb

 

136

 

 

PPhPr2

N Si   As Sb

8

138

1

0

PMe(m-MeC6H4)2

N Si   As Sb

10.4

138

2

0

PMe(m-ClC6H4)2

N Si   As Sb

15.9

138

2

0

PCl(p-MeC6H4)2 N Si   As Sb
21.7
138
3.4
3.6

PPh2Cl

N Si Sn As Sb

22.8

138

3.4

1.8

P(t-Bu)Me2

N Si   As Sb

5.7

139

0

0

PEt(i-Bu)2

N Si   As Sb

5.9

139

0

0

PPhBu2

N Si   As Sb

8.1

139

1.3

0

P(Cl)(NC4H8)2

N Si   As Sb

13.2

139

1.0

2.4

PPh2(OC6H5)

N Si   As Sb

16.7

139

2.4

1.4

PCl2Cy

N Si Sn As Sb

28.5

139

2.8

3.6

           
140
   

PPh2Et

N Si   As Sb

11.1

140

2.3

0

PEt(p-ClC6H4)2

N Si   As Sb

13.3

140

2

0

PPh2Vi

N Si   As Sb

13.65

140

0

P(C6F5)Me2 N Si   As Sb
17.3
140
1.4
0

PPh2(CH2CH2CN)

N Si   As Sb

14.5

140

2

0.4

PBrPh2

N Si Sn As Sb

22

140

PPh2Pr

N Si   As Sb

10.6

141

2

0

PPh2Bu

N Si   As Sb

11.3

142

2.1

0

PPh2CH2CH2C6F13

N Si   As Sb

13.3

142

2

0.8

P(i-Bu)3

N Si   As Sb

5.7

143

0

0

P(i-Pr)2OCH2CH2C6F13

N Si   As Sb

P(t-Bu)Cl2

N Si   As Sb

28

143

2.7

3.5

PCy2H

N Si   As Sb

6.6

144

0

1.2

P(C6F5)Cl2 N Si Sn As Sb
39.6
144
4.1
3.5

P(p-Me2NC6H4)3

N Si   As Sb

5.25

145

2.7

0

P(p-MeOC6H4)3

N Si Sn As Sb

10.5

145

2.7

0

PPh2(p-Me2NC6H4)

N Si   As Sb

10.6

145

2.7

0

P(p-MeC6H4)3

N Si Sn As Sb

11.5

145

2.7

0

PCy(CH2CH2CN)2

N Si   As Sb

11.8

145

0

0.8

PPh2(p-MeC6H4)

N Si   As Sb

12.8

145

2.7

0

PPh2(p-MeOC6H4)

N Si   As Sb

12.3

145

2.7

0

P(C6H5)3

N Si Sn As Sb

13.25

145

2.7

0

PPh2(p-FC6H4)

N Si   As Sb

14.1

145

2.7

0

PPh2(p-ClC6H4)

N Si   As Sb

14.4

145

2.7

0

PPh(p-FC6H4)2

N Si Sn As Sb

14.9

145

2.7

0

PPh(p-ClC6H4)2

N Si Sn As Sb

10.8

136

2

0

P(p-FC6H4)3

N Si Sn As Sb

15.7

145

2.7

0

PPh2(p-F13C6Ph)

N Si   As Sb

16.5

145

2.7

0

P(p-ClC6H4)3

N Si Sn As Sb

16.8

145

2.7

0

PPh(p-F13C6Ph)2

N Si   As Sb

19.8

145

2.7

0

PPh2(Pyr)

N Si   As Sb

19.5

145

3.1

0.6

P(p-F3CC6H4)3

N Si   As Sb

20.5

145

2.7

0

P(p-F13C6Ph)3

N Si   As Sb

23

145

2.7

0

PPh2[Pyr-3,4-(CO2Et)2]

N Si   As Sb

23.2

145

3.1

0.7

PPh(Pyr)2

N Si   As Sb

25.7

145

3.2

1.3

P(Pyr)3

N Si   As Sb

31.9

145

3.3

1.9

PPh[Pyr-3,4-(CO2Et)2]2

N Si   As Sb

33.1

145

3.2

1.4

P[Pyr-3,4-(CO2Et)2]3

N Si   As Sb

43

145

3.3

2

P(p-MeSC6H4)3

N Si Sn As Sb

145

2.7

0

P(p-MeSO2C6H4)3

N Si Sn As Sb

145

2.7

0

P(p-BrC6H4)3

N Si Sn As Sb

 

 

 

 

P(p-EtC6H4)3

N Si Sn As Sb

 

 

 

 

PMe(i-Pr)2

N Si   As Sb

5.7

146

0

0

P(NC4H8)3

N Si   As Sb

-1.2

146

-0.6

0.9

PPh(m-ClC6H4)2

N Si Sn As Sb

17.7

147

2.7

0

P(m-MeC6H4)3

N Si   As Sb

11.3

148

2.7

0

PEt2(C6F5)

N Si Sn As Sb

15.8

148

1.4

0

P(m-ClC6H4)3

N Si   As Sb

19.6

148

2.7

0

PEt2(t-Bu)2

N Si   As Sb

4.2

149

0

0

PPh(C6HF5)Me N Si   As Sb
18.9
149
2.3
0
           
150
   

P(t-Bu)2H

N Si   As Sb

5.7

150

0

1.2

PCy2OCH2CH2C6F13

N Si   As Sb

P(i-Pr)Ph2

N Si   As Sb

9.6

150

1.7

0

PEt(i-Pr)2 N Si   As Sb
4.4
151
0
0

P(t-Bu)(CF3)2

N Si Sn As Sb

22

151

0

7.4

P(i-Pr)2CH2CH2C6F13

N Si   As Sb

6.8

152

0

0.8

PCy2Me N Si   As Sb
3.8
153
0
0

PPh2Cy

N Si   As Sb

9.1

153

1.6

0

P(i-Pr)2(p-MeC6H4)

N Si   As Sb

6.1

155

1

0

PPh(i-Pr)2

N Si   As Sb

10

155

2

0

PPh2(o-MeC6H4) N Si   As Sb
12.4
156
2.7
0

P(t-Bu)2F

N Si   As Sb

11

156

0

4.4

P(CH2CH2CN)Cy2

N Si   As Sb

6.6

157

0

0.4

PPh2(t-Bu)

N Si   As Sb

8.8

157

2

0

PMe(o-MeC6H4)2

N Si   As Sb

9.9

158

2

0

PPh2(C6F5) N Si Sn As Sb
20.2
158
3.2
0

PCy2CH2CH2C6F13

N Si   As Sb

5.4

159

0

0.8

       
160
   
P(t-Bu)2(NH2) N Si   As Sb
160?

P(i-Pr3)

N Si   As Sb

3.45

160

0

0

PMe(t-Bu)2 N Si   As Sb
2.85
161
0
0

PPhCy2

N Si   As Sb

5.7

162

1.6

0

PMe(C6F5)2 N Si Sn As Sb

26.1

162

2.7

0

P(t-Bu)2Cl

N Si   As Sb

14

163

1.4

1.8

PCl(C6F5)2 N Si Sn As Sb
36.8
164
4.1
3.6
PBz3 N Si Sn As Sb
10.65
165
PEt(C6F5)2 N Si Sn As Sb

25.3

167

2.7

0

       
170
   

PCy3

N Si Sn As Sb

1.4

170

0

0

PPh(C6F5)2 N Si Sn As Sb
27.1
171
3.6
0
PCy2(t-Bu) N Si   As Sb
0.95
174
0
0

P(o-MeC6H4)

N Si   As Sb

10.65

178

2.7

0

         
180
   
P(t-Bu)3 N Si   As Sb
0
182
0
0

P(C6F5)3

N Si Sn As Sb

34.8

184

4.1

0

       
Misc
   
P-C-Hal                  
PF2(CH2Cl) N Si Sn As Sb

 

 

 

 

PF2(CCl3) N Si   As Sb        
P(CH2Cl)(OEt)2 N Si Sn As Sb

 

 

 

 

P(CH2Cl)(OMe)2 N Si Sn As Sb

 

 

 

 

PH(CH2Cl)(OMe) N Si Sn As Sb

 

 

 

 

P(CH2Cl)2(OMe) N Si Sn As Sb

 

 

 

 

PCl(CH2Cl)2 N Si Sn As Sb

 

 

 

 

PMe(CH2I)2 N Si   As Sb
PBu2(CH2Cl) N Si   As Sb
P(ClCH2)Me2 N Si   As Sb
P(ClCH2)2Me N Si   As Sb
P(CCl3)(OMe)2 N Si Sn As Sb

 

 

 

 

PPCl(CCl3)2 N Si Sn As Sb

 

 

 

 

PCl2(CCl3) N Si   As Sb        
PCl2(CH2Cl) N Si   As Sb        
PCl(CH2Cl)(OEt) N Si Sn As Sb

 

 

 

 

PCl(C2F5) N Si Sn As Sb

 

 

 

 

PCl2(C2F5) N Si Sn As Sb

 

 

 

 

P(CF2CCl=CF2)(OMe)2 N Si Sn As Sb

 

 

 

 

P(CF3)2(NMe2) N Si Sn As Sb

 

 

 

 

PMe2(CH2Br) N Si   As Sb
PMe2(CH2I) N Si   As Sb
P-R, Vi, Allyl etc.                  
PMe2(decyl) N Si   As Sb        
DMPP N Si   As Sb        
DPPE N Si   As Sb        
1-phospha[2,2,1]-heptane N Si   As Sb        
P(neoPentyl)PhMe N Si   As Sb        
PMe2(neopentyl) N Si   As Sb
PMe(i-pentyl)2 N Si   As Sb
PEt(i-pentyl)2 N Si   As Sb
P(i-pentyl)3 N Si   As Sb
P(allyl)Bu2 N Si   As Sb        
PMe2(CH2CH=CH2) N Si   As Sb
PMe(CH2CH=CH2)2 N Si   As Sb
P(CH2CH=CH2)3 N Si   As Sb
PMe2(C2H) N Si   As Sb
P(C2H)3 N Si   As Sb
P(CC-t-Bu) N Si   As Sb        
P(2-ethylhexyl)3 N Si   As Sb        
P(i-pentyl)3 N Si   As Sb        
P(i-pentyl)(0ctyl)2 N Si   As Sb        
P(s-hexyl)3 N Si   As Sb        
PH(neopentyl)2 N Si   As Sb        
PH2(octyl) N Si   As Sb        
PPh(octyl)2 N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
P-N                  
P(NEt2)F2 N Si   As Sb        
P(NMe2)F2 N Si   As Sb        
P(NMe2)Cl2 N Si   As Sb        
P(NMe2)2Cl N Si   As Sb        
P(NEt2)3 N Si   As Sb        
P(NPr2)3 N Si   As Sb        
P(N(pentyl)2)3 N Si   As Sb        
P(NMe2)2(OMe) N Si   As Sb        
P(NMe2)(OMe)2 N Si   As Sb        
P(NMe2)2(OEt) N Si   As Sb        
PNMe2(O-i-Pr) N Si   As Sb        
P(NMe2)(OMe)2 N Si   As Sb        
PTA N Si   As Sb        
P(NMe2)3 N Si   As Sb        
PMe2(NMe2) N Si   As Sb
PMe(NMe2)2 N Si   As Sb
PClMe(NMe2) N Si   As Sb        
P(N(i-Bu)2)3 N Si   As Sb        
P(NBu2)2(OBu) N Si   As Sb        
P(NBu2)(OBu)2 N Si   As Sb        
P(NBu2)3 N Si   As Sb        
P(NHBu)(OBu)2 N Si   As Sb        
P(NHBu)2(OBu) N Si   As Sb        
P(NHBu)3 N Si   As Sb        
P(NMe2)(OEt)2 N Si   As Sb        
PMe(NBu2)2 N Si   As Sb        
PMe(NMe2)(OMe) N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
P-Aryl                  
P(m-CF3C6H4)Me2 N Si   As Sb        
P(o-CF3C6H4)3 N Si   As Sb        
P(m-CF3C6H4)3 N Si   As Sb        
PMe2(p-O2NC6H4) N Si   As Sb
PMe(m-O2NC6H4)2 N Si   As Sb        
PMe2(m-MeOC6H4) N Si   As Sb
PMe2(o-MeOC6H4) N Si   As Sb        
P((m-MeOC6H4) N Si   As Sb
PPh2(o-MeOC6H4) N Si   As Sb
P(o-MeOC6H4)3 N Si   As Sb        
P(2,6-(MeO)2C6H4)3 N Si   As Sb        
P(2,4,6-Me3C6H4)3 N Si   As Sb        
PPh2(m-FC6H4) N Si   As Sb
P(m-FC6H4)3 N Si   As Sb
P(m-BrC6H4)3 N Si   As Sb        
P(m-FC6H4)2(p-FC6H4) N Si   As Sb        
P(m-FC6H4)3 N Si   As Sb        
P(m-O2NC6H4)3 N Si   As Sb        
P(m-FC6H4)(p-FC6H4)2 N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
P-Bz (benzyl)                  
PBz(p-MeC6H4)2 N Si   As Sb
PBzMe2 N Si   As Sb
PBz2Me N Si   As Sb
PBzPh2 N Si   As Sb
PPh2(p-MeBz) N Si   As Sb
PPh2(p-MeOBz) N Si   As Sb
PPh2(p-MeBz) N Si   As Sb
PBz2H N Si   As Sb
PBzEt2 N Si   As Sb        
PBz(i-Pr)2 N Si   As Sb        
PBu2Bz N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
P-C-SiZ3                  
PMe2(CH2SiMe3) N Si   As Sb        
PMe2C(SiMe3)3 N Si   As Sb        
P-OR                  
P(O)(OEt)2(-) N Si   As Sb        
P(OH)(OEt)2 N Si   As Sb        
P(OH)3 N Si   As Sb        
P(O)(OH)2(-) N Si   As Sb        
PMe2(OSiMe3) N Si   As Sb
P(O-i-Bu)3 N Si   As Sb
P(O-s-Bu)3 N Si   As Sb
P(O-2-ethylhexyl)3 N Si   As Sb        
P(OMe)(OCH2CH2O) N Si   As Sb        
P(O-allyl)3 N Si   As Sb
P(O-t-Bu)3 N Si   As Sb        
P(2-ethylhexyl)2(O-2-ethylhexyl) N Si   As Sb        
P(cresyl)3 N Si   As Sb        
P(O-2,4-Cl2C6H3)3 N Si   As Sb        
P(O-i-Bu)2(O-p-ethylhexylC6H4) N Si   As Sb        
P(O-m-MeC6H4)3 N Si   As Sb        
P(O-o-MeC6H4)3 N Si   As Sb        
P(OEt)2(O-p-ethylhexylC6H4) N Si   As Sb        
P(OEt)(O-p-ethylhexylC6H4)2 N Si   As Sb        
P(O-octyl)3 N Si   As Sb        
P(O-p-O2NC6H4)3 N Si   As Sb        
P(O-amyl)3 N Si   As Sb        
P(OCH2CH2Br)(OMe)2 N Si   As Sb        
P(octyl)(O-octyl)2 N Si   As Sb        
P(octyl)2(O-octyl) N Si   As Sb        
P(OEt)2(p-O2NC6H4) N Si   As Sb        
P(OMe)(O-p-2,4-Cl2C6H3)2 N Si   As Sb        
P(OMe)(O-p-O2NC6H4)2 N Si   As Sb        
P(OMe)2(O-2,4-Cl2C6H3) N Si   As Sb        
P(cresyl)(OPh)2 N Si   As Sb        
PH(O-2-ethylhexyl)2 N Si   As Sb        
PMe2(O2CPh) N Si   As Sb        
PVi(OCH2CH2Cl)2 N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
P-Misc                  
PH(2,2-biphenylene) N Si   As Sb
P(perhydro-1-napthyl)3 N Si   As Sb
P(a-Np)PhMe N Si   As Sb        
P(a-Np)(m-FC6H4)Me N Si   As Sb        
P(a-Np)(m-MeOC6H4)Me N Si   As Sb        
P(a-Np)(m-CF3C6H4)Me N Si   As Sb        
P(a-Np)(p-MeC6H4)Me N Si   As Sb        
P(a-Np)(p-MeOC6H4)Me N Si   As Sb        
P(a-Np)(p-CF3C6H4)Me N Si   As Sb        
P(a-Np)(C6HF5)Me N Si   As Sb        
PNpPh2 N Si   As Sb        
PNp2Ph N Si   As Sb        
PNp3 N Si   As Sb        
PAnPh2 N Si   As Sb        
PAn3 N Si   As Sb        
P-Br                  
PBr2(OMe) N Si   As Sb        
P-X                  
P(N3)3 N Si Sn As Sb        
P(NCO)3 N Si   As Sb        
P(NCS)3 N Si   As Sb        
P-Cl                  
PCl2(O-t-Bu) N Si   As Sb        
P-I                  
PI3 N Si Sn As Sb
34.4
     
PF2I N Si   As Sb 33.5      
PIMe2 N Si Sn As Sb 17.2      
PIPh2 N Si Sn As Sb 20.3      
PI2Me N Si Sn As Sb 25.8      
PI2Ph N Si Sn As Sb 27.4      
PI2(NHCy) N Si   As Sb        
P-Si                  
PMe2(SiMe3) N Si   As Sb        
P(SiH3)3 N Si   As Sb        
P-S                  
P(SMe)3 N Si   As Sb        
P(S-i-Pr)3 N Si   As Sb        
P(SEt)3 N Si   As Sb        
PCl(SMe)2 N Si   As Sb        
PCl2(SMe) N Si   As Sb        
PClMe(SEt)) N Si   As Sb        
PF2(SMe) N Si   As Sb        
P(OMe)(SMe)2 N Si   As Sb        
P(OMe)2(SMe) N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
P-CN                  
P(CN)F2 N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
N Si   As Sb        
                   
                   
                   

acd values for the phosphines and phosphites are taken from references 1, 2, 3,4, and 5 or calculated by additivity using the data found in these references.

bValues for cone angles (q) are taken from references 6 and 5 or calculated by additivity using the data found in these references.

c) Ear values are taken from references 2, 4, 3.and 5.

d) pp values are taken from references 4, 5 and 3

References

 

1. Bartik, T., Himmler, T., Schulte, H.-. and Seevogel, K.J.: Substituenteneinflusse aud die Basizitat von Phosphorliganden in R3PNi(CO)3-Komplexen. J. Organomet. Chem. 272, 29 (1984)

2. Fernandez, A.L., Lee, T.Y., Reyes, C., Prock, A., Giering, W.P., Haar, C.M. and Nolan, S.P.: A thermodynamic method based on isoequilibrium behavior to determine
the values of stereoelectronic parameters of phosphines. J. C. S. Perkin Trans. 2 2631 (1999)

3. Woska, D., Prock, A. and Giering, W.P.: Determination of the Stereoelectronic Parameters of PF3, PCl3, PH3, and P(CH2CH2CN)3. The Quantitative Anlysis of LIgand Effects (QALE). Organometallics 19, 4629 (2000).

3a. Fernandez, A. L., Wilson, M. R., Prock, A., Giering, W. P.Evaluation of the Syereoelectronic Parameters of Fluorous Phosphorus(Iii) Ligands. The Qunatitative Analysis of Ligand Effects. Submitted for publicationi.

4. Fernandez, A.L., Reyes, C., Prock, A. and Giering, W.P.: The Stereoelectronic Parameters of Phosphites. The Quantitative Analysis of Ligand Effects (QALE). Perkin Trans 2 1033 (2000)

5. Fernandez, A.L., Reyes, C., Lee, T.Y., Prock, A., Giering, W.P., Haar, C.M. and Nolan, S.P.: Assessing the Stereoelectronic Properties of Pyrrolyl Phosphines and Related LIgands. The Quantitative Analysis of Ligand Effects. (QALE). Perkin Trans. 2 1349 (2000)

6. Tolman, C.A.: Steric Effects of Phosphorus Ligands in Organometallic Chemistry and Homogeneous Catalyst. Chem. Rev. 77, 313 (1977)