11137660
123.220 Experiment 7
Enthalpy of Protonation of Glycine
Introduction
Glycine, the smallest amino acid is known to be ambivalent (able to be either inside or outside of the
protein molecule) due to the presence of amine (-NH2) and carboxylate (-COOH) groups in the
molecule. Glycine can behave as base to produce (+NH3CH2COO) ion in acidic solution and able to
act as acid to produce (NH2CH2COO-) ion in basic solutions.
In aqueous solution, glycine may be present as a dipolar ion or better called zwitterion
(+NH3CH2CO2-). The equilibrium constant of the protonation of the amine functional group is
shown below:
(NH2CH2CO2-)
+ H+
(+NH3CH2CO2-)
Based on the titration of this species with a base, the enthalpy change for the reaction can be
determined using the vant Hoff equation,
H 1 1
( ) ln k 2 ln k1
R
T2 T1
Where:
is the equilibrium constant at ,
is the equilibrium constant at ,
R is a constant = 8.314 J/mol K.
25
of the glycine/KCl solution was pipetted into clean dry titration cell. The solution was titrated
using 0.10 mol/
NaOh/0.10 mol/
KCl solution. pH of titrant volumes of 13 values up to 10
was recorded and the pH titration curve was constructed. The steps were repeated with the
water bath is set to 43.5 C.
Further explanation of the procedures may be referred to Advanced Chemistry Lab Manual page 47
and 48.
Vol/mL
0
0.5
1
1.5
2.05
3
4.2
5
6.4
7.1
8
9
10
pH
7.06
8.03
8.65
9.01
9.26
9.46
9.67
9.85
10.12
10.22
10.43
10.71
11.07
[H+]
8.70964E-08
9.33254E-09
2.23872E-09
9.77237E-10
5.49541E-10
3.46737E-10
2.13796E-10
1.41254E-10
7.58578E-11
6.0256E-11
3.71535E-11
1.94984E-11
8.51138E-12
tvol
25
25.5
26
26.5
27.05
28
29.2
30
31.4
32.1
33
34
35
TA
0.040537
0.039742
0.038978
0.038243
0.037465
0.036194
0.034706
0.033781
0.032275
0.031571
0.03071
0.029807
0.028955
alka [-OH]
0
0.0018431
0.0036154
0.0053208
0.0071238
0.0100714
0.0135205
0.0156667
0.0191592
0.0207913
0.0227879
0.0248824
0.0268571
TH
0.040537
0.037899
0.035363
0.032922
0.030341
0.026122
0.021186
0.018114
0.013116
0.01078
0.007922
0.004924
0.002098
para-1
4.05E-02
3.79E-02
3.54E-02
3.29E-02
3.04E-02
2.62E-02
2.13E-02
1.82E-02
1.33E-02
1.11E-02
8.40E-03
5.83E-03
4.17E-03
para-2
-1.15E-07
1.84E-03
3.61E-03
5.30E-03
7.09E-03
1.00E-02
1.34E-02
1.55E-02
1.89E-02
2.05E-02
2.23E-02
2.40E-02
2.48E-02
Kc
-4.05E+12
2.21E+09
4.38E+09
6.36E+09
7.79E+09
7.53E+09
7.40E+09
8.31E+09
9.30E+09
8.96E+09
1.01E+10
1.25E+10
1.97E+10
Vol/mL
0
0.5
1
1.5
2
3
4
5
6
7
8
9
10
pH
7.4
8.16
8.31
8.42
8.62
9.01
9.19
9.33
9.52
9.66
9.74
9.84
10.16
[H+]
tvol
TA
alka [-OH] TH
para-1
para-2
Kc
3.98107E-08
25 0.040537
0 0.040537 4.05E-02 -4.02E-07 -2.53E+12
6.91831E-09
25.5 0.039742 0.0018431 0.037899 3.79E-02 1.84E-03 2.98E+09
4.89779E-09
26 0.038978 0.0036154 0.035363 3.54E-02 3.61E-03 2.00E+09
3.80189E-09
26.5 0.038243 0.0053208 0.032922 3.29E-02 5.32E-03 1.63E+09
2.39883E-09
27 0.037534 0.006963 0.030571 3.06E-02 6.96E-03 1.83E+09
9.77237E-10
28 0.036194 0.0100714 0.026122 2.61E-02 1.01E-02 2.66E+09
6.45654E-10
29 0.034946 0.0129655 0.02198 2.20E-02 1.29E-02 2.63E+09
4.67735E-10
30 0.033781 0.0156667 0.018114 1.82E-02 1.56E-02 2.48E+09
3.01995E-10
31 0.032691 0.0181935 0.014498 1.46E-02 1.81E-02 2.66E+09
2.18776E-10
32 0.03167 0.0205625 0.011107 1.12E-02 2.05E-02 2.50E+09
1.8197E-10
33 0.03071 0.0227879 0.007922 8.02E-03 2.27E-02 1.94E+09
1.44544E-10
34 0.029807 0.0248824 0.004924 5.05E-03 2.48E-02 1.41E+09
6.91831E-11
35 0.028955 0.0268571 0.002098 2.35E-03 2.66E-02 1.28E+09
temperature, C average Kc
standard deviation
25
8.07E+09
76988075
43.5
2.59E+09
88959032.91
Table 3: average and standard deviation values at each temperature
Based on Table 3 above, the average Kc value at 25 C is higher compared to that at 43.5 C. This
indicates that more dipolar ion (zwitterion) was produced at 25 C compared when at 43.5C.
The titration curve for both temperatures were produced and presented in Graph 1 and Graph 2.
Both graphs gave increasing linear trend lines indicating that as the volume of NaOH (base) increases,
the pH of glycine increases (becoming more alkaline).
volume of NaOH
10
8
6
4
2
0
0
pH
10
12
10
8
6
4
2
0
0
pH
Calculations
10
12
2.
Conclusion
As a conclusion, protonation of glycine depends on the temperature and thus, affecting the enthalpy
of its protonation.