1. © The Author(s) 2013. Published by Science and Education Publishing.
Table 1. Taft *, pKa, nucleophilicities (n) and dipole moments of different amines. All the physical quantities are from references
Sl.No.
Amine
*
pKa
(aq.sol.) n
Dipole moments in
Benzene
Cyclohexane
Gas phase
Pure liquids 1
NH3
1.47
9.21
4.23 2
H2NNH2
1.60
8.10
1.75 3
CH3NH2
0.98
10.62
5.20
1.31 4
C2H5NH2
0.88
10.63
4.93
1.22 5
n-PrNH2
0.86
10.53
1.35
1.34
1.17 6
n-BuNH2
0.79
10.43
5.04
1.45
1.00 7
i-PrNH2
4.68
1.19 8
sec-BuNH2
0.77
10.56
1.28 9
t-BuNH2
0.68
10.45
1.29 10
i-BuNH2
0.85
10.59
4.99
1.27 11
CH2=CHCH2NH2
1.11
9.49
1.32
1.2 12
HOCH2CH2NH2
1.18
9.50 13
NH2CH2CH2NH2
1.06
9.98 14
C6H5CH2NH2
1.20
9.34
1.38
1.15 15
C6H5NH2
1.58
9.13
1.53 16
cy-C6H13NH2
0.83
10.64
1.26 17
(CH3)2NH
0.49
5.63
1.03 18
(C2H5)2NH
0.29
10.98
4.75
0.92 19
(n-Pr)2NH
0.25
11.0
1.01 20
(i-Pr)2NH
0.11
11.05 21
(n-Bu)2NH
0.23
11.25
4.77
1.12
1.09 22
(i-Bu)2NH
10.5
4.60
1.10 23
C6H5CH2(Et)NH
0.61
10.3 24
(C6H5CH2)2NH
0.93
8.52
1.02
0.97 25
C6H5(CH3)NH
4.85
1.67 26
(CH2CH2OH)2NH
0.89
7.76
2.84 27
(CH3)3N
0.00
9.76
6.00
0.612 28
(C2H5)3N
-0.30
10.65
4.09
0.81
0.78
0.66 29
(n-Bu)3N
-0.39
10.89 30
(CH2CH2OH)3N
0.60
7.77
3.57 31
(C6H5CH2)3N
7.10
0.65 32
C6H5(CH3)2N
8.35 33
C6H5(C2H5)2N
0.40
7.44
1.80
1.40 34
pyrrolidine
11.27
5.67 35
piperdine
0.35
11.22
5.59 36
(CH3)2N(C2H5)
-0.10
10.36
5.44 37
(CH3)2N(n-C4H9)
-0.19
10.06
5.38 38
(CH3)N(C2H5)2
-0.20
10.29
4.80
R. Sanjeev et al. Significance of Nucleophilic Solvation of Ammonium Bond (≡N+-H) in Protonated Amines: A Thought Provoking Physical-Organic Chemistry Lecture to Graduate Students. World Journal of Chemical Education, 2013, Vol. 1, No. 1, 1-5. doi: /wjce-1-1-1
© The Author(s) Published by Science and Education Publishing.