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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-)

From the reaction, K can be expressed as,

Based on the titration of this species with a base, the enthalpy change for the reaction can be
determined using the vant Hoff equation,

and by assuming that

is independent of T, integrating the above equation gives,

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.

Procedure

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0.3043 g of glycine was weighed and transferred into 100
volumetric flask. 10
of 2.0
mol/
KCl was then added and made to the mark using distilled water. The water bath was set to
25 C. The apparatus was set up as Figure 1.

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.

Results and Discussions

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The data collected were tabulated and treated according to both temperatures 25C and 43.5C set
during the experiment. Using the values calculated, the Kc value for each temperature was averaged
and the standard deviation was obtained.
In Table 1 and Table 2, the Kc values for NaOH volume of 0 mL gave negative values of -4.05E+12 and
-2.53E+12 respectively. Inconsistencies of the Kc values for both experimented temperatures were
also notified in both tables. These may be due to improper cleansing of the titration cell giving
inaccurate pH readings.

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

Table 1: Data of the experiment at 25C

Vol/mL
0
0.5
1
1.5
2
3
4
5
6
7
8
9
10

pH

[H+]
tvol
TA
alka [-OH] TH
para-1
para-2
Kc
7.4 3.98107E-08
25 0.040537
0 0.040537 4.05E-02 -4.02E-07 -2.53E+12
8.16 6.91831E-09
25.5 0.039742 0.0018431 0.037899 3.79E-02 1.84E-03 2.98E+09
8.31 4.89779E-09
26 0.038978 0.0036154 0.035363 3.54E-02 3.61E-03 2.00E+09
8.42 3.80189E-09
26.5 0.038243 0.0053208 0.032922 3.29E-02 5.32E-03 1.63E+09
8.62 2.39883E-09
27 0.037534 0.006963 0.030571 3.06E-02 6.96E-03 1.83E+09
9.01 9.77237E-10
28 0.036194 0.0100714 0.026122 2.61E-02 1.01E-02 2.66E+09
9.19 6.45654E-10
29 0.034946 0.0129655 0.02198 2.20E-02 1.29E-02 2.63E+09
9.33 4.67735E-10
30 0.033781 0.0156667 0.018114 1.82E-02 1.56E-02 2.48E+09
9.52 3.01995E-10
31 0.032691 0.0181935 0.014498 1.46E-02 1.81E-02 2.66E+09
9.66 2.18776E-10
32 0.03167 0.0205625 0.011107 1.12E-02 2.05E-02 2.50E+09
9.74 1.8197E-10
33 0.03071 0.0227879 0.007922 8.02E-03 2.27E-02 1.94E+09
9.84 1.44544E-10
34 0.029807 0.0248824 0.004924 5.05E-03 2.48E-02 1.41E+09
10.16 6.91831E-11
35 0.028955 0.0268571 0.002098 2.35E-03 2.66E-02 1.28E+09

Table 2: Data of the experiment at 43.5 C

temperature, C average Kc
standard deviation
25
8.07E+09
76988075
43.5
2.59E+09
88959032.91

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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).

NaOH (mL) vs pH at 25C

12

volume of NaOH

10
8
6
4
2
0
0

pH

Graph 1: Total volume of NaOH (mL) against pH at 25C

10

12

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NaOH (mL) vs pH at 43.5 C

12

Volume of NaOH (mL)

10
8
6
4
2
0
0

10

12

pH

Graph 2: Total volume of NaOH (mL) against pH at 43.5C

Calculations

Exercises
1. Literature value of

(R. M. Izatt, 1992 retrieved on 27th September 2012)

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Actual value calculated:

2.

Conclusion
As a conclusion, protonation of glycine depends on the temperature and thus, affecting the enthalpy
of its protonation.