Bond Rotation
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C-C Bond Rotation
Dr. Edmund Nip
Chem 301-61
Hampton University
October 2, 2018
Hannah Collins
Lindsey Johnson Ashley Manuel
Abstract In this experiment the bond rotation between carbon 2 and carbon 3 was observed. The bond was
rotated every 10 degrees from 0 until 360 degrees was reached. Chem draw was used to draw structures and rotate the bond angles to find the dihedral angle and the corresponding energy of the molecule every 10 degrees until 360 degrees was reaches. This was the purpose of the experiment. Background
A Newman projection is a drawing convention. The bond looks down a specific bond and the bond being looked down was between C2 and C3. Most rotated molecules are rotated 60 degrees
all the way until 360 degrees but in this lab rotation was done every 10 degrees. Bond rotation strains are caused by the electrons in between different groups. Torsional strain is when the repulsion caused by the electrons in between different groups when they pass b each other. When a molecule is rotated around the sigma bond, there is going to be different levels of torsional strains that can change the placements of the substituents. This is how we come up with different conformations of molecules like staggered or eclipsed and the different energy levels and stability levels as well. The reagents that are being used within the system to do bond rotations is butane, 2-methylbutane, and 2,3-dimethylbutane. When you move
the bonds around the different arrangements are a result of the sigma bond rotation that is known
as conformations. This strain is due to electron repulsion or when it is not in its ideal geometry.
Purpose
To draw structures using ChemMagic and rotate the structures to find the cinedral angle and the corresponding energy of the molecules every 10 degrees until 360 degrees was reached.
Table of Reagents Compound molecular weight amount used B.P/M.P
density
Butane 58.12 g/mol
N/A
30.2
0
F/-220
0
F 2.48kg/m
3
2-methyllbutane 72.15g/mol
N/A
27.8
0
C/-160
0
C 616 kg/m
3
2,3-dimethylbutane 86.17g/mol N/A
58.3
0
C/-124
0
C 660 kg/m
3
Hazards Butane : extremely flammable and explosive
2-methylbutane: extremely flammable liquid and vapor
2 3-dimethylbutane: highly flammable liquid and vapor
Procedure The ChemMagic site was opened on a web browser. The “draw” button was selected under the “load Models” section. The skeletal structure of the compound, butane, was drawn. The “load models” button was clicked on once the structure was complete. The 3D model of the structure appeared and then the structure was optimized by selecting the “optimize” button under
the “Other Model Actions” section. The optimization number appeared at the top of the page. Next, “torsion” was clicked on under the “Other Model Actions” section. Four connected carbon atoms on the structure were clicked on an angle close to 180
0
appeared between the atoms. “Rotate bond” was selected and then the C2-C3 bond was clicked on. Then, the carbons were circled in red. The bond angle was rotated as close as possible to 0
0
. Under the “Other Model Actions” section “energy” was selected. The energy in KJ appeared on the screen. The bond angle and energy was recorded. “Rotate bond” was clicked on angle and the angle was rotated 10
0
. The energy button was selected and the bond angle and energy were recorded again. This part was repeated until the bond rotated 360
0
. This entire procedure was done for 2-methylbutane
and 2,3-dimethylbutane as well, making sure the center C-C bond was selected and rotated.
Data Butane bond angle
energy
0.2
26.375
10.2
23.22
20
16.12
30
7.933
40
0.468
50
-6.218
60
-11.774
70
-14.739
80
-14.414
90
-11.51
100
-7.783
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110
-4.86
120
-3.806
130
-4.988
140
-8.135
150
-12.45
160
-16.796
170
-19.996
180
-21.168
190
-19.984
200
-16.775
210
-12.425
220
-8.115
230
-4.976
240
-3.806
250
-4.871
260
-7.797
270
-11.525
280
-14.412
290
-14.742
300
-11.741
310
-6.217
320
0.47
330
7.937
340
16.124
350
23.363
360
26.376
0
50
100
150
200
250
300
350
400
-30
-20
-10
0
10
20
30
Bond rotation C-C bonds (butane)
Bond Angle
Energy level (kJ/mol)
2-methylbutane bond angle
energy
0.4
36.293
10.4
33.659
20.4
27.458
30.4
20.088
40.4
13.529
50.4
8.962
60.4
7.183
70.4
8.414
80.8
12.107
90.8
16.764
100.6
21.444
110.5
25.212
120.9
26.758
130.9
24.867
140.9
20.06
150.3
14.282
160.3
8.427
170.3
4.035
180
1.885
190
2.266
200.6
4.907
210.7
9.252
220.7
14.023
230.9
17.05
240.7
19.427
250.7
18.607
260
15.331
270.6
11.299
280.6
7.374
290.8
5.57
300.8
6.919
310.8
11.07
320.8
16.575
330.9
36.293
340.8
33.659
350.8
27.458
360.8
20.088
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2,3-dimethylbutane
0.6
71.608
10.7
67.808
20.6
59.638
30.6
50.416
40.7
42.303
50.7
36.258
60.7
33.043
70.6
33.497
80.7
37.327
90.7
43.043
100.2
49.063
110.6
54.55
120.8
56.56
130.8
53.868
140.7
47.591
150.3
40.176
160.8
33.139
170.8
28.809
180
27.461
189.6
28.912
199.1
33.102
210
40.395
219.2
47.456
229.3
53.951
239.4
56.565
249.1
54.665
259.4
49.404
269.1
43.148
279.4
37.269
289.2
33.55
299.4
33.064
309.3
36.287
319.2
42.249
329.7
50.445
339.1
59.359
349.4
67.87
359.8
71.619
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Discussion
During the lab the purpose was to use Chemdraw to draw structures and rotate the bond angles to
find the dihedral angle and the corresponding energy of the molecule every 10 degrees until 360 degrees was reached. The graphs of the substances corresponded to the amount of energy that each bond produced. The local maxima for butane was at 0 degrees, 120 degrees, 240 degrees, and 360 degrees. The local minima for butane was 70 degrees, 180 degrees, 290 degrees. For 2,3-dimethylbutane the local maxima was 0.6 degree, 120.8 degrees, 239.4 degrees, and 359.8 degrees. The local minima for 2,3-dimethylbutane is 70.6 degrees, 180 degree, and 299.4 degrees. The local maxima for 2-methylbutane is 0.4 degrees, 120.9 degrees, 240.7 degrees, and 330.9 degrees. The local minima of 2-methylbutane is 60.4 degrees, 180 degrees, 290.8 degrees, and 360.8 degrees. In comparison the graphs shows the different energy that corresponds to the Newman projection of each substance. When two large atoms are next to each other they create tension which leads to an eclipsed projection having more energy than a staggered projection. This can be shown in the graph as well and for such reason I believe that the maxima and minima for each compound was what is to be expected. Possible errors that could potentially alter the data would have been the accuracy in collecting data. When conducting the experiment it was a challenge keeping consistent numbers when evaluating the bond angles. In conclusion the observation of angles with their energy was observed and compared to one another. This affected their Newman projections and their corresponding energies as seen in the graph.
References
Bump, Charles. (2007).
Organic Laboratory Experiments: Semi and Microscale Investigations in
General Organic Chemistry. Mason, Ohio.
Libretexts. (2016, July 21)/ 2.10: Rotation Occurs About Carbon-Carbon Single Bonds. Retrieved from https://chem.libretexts.org/Textbook_Maps/Organic_Chemistry/Map
%3A_Organic_Chemistry_(Bruice)/02%3A_An_Introduction_to_Organic_Compounds
%3A_Nomenclature%2C_Physical_Properties%2C_and_Representation_of_Structure/
2.10%3A_Rotation_Occurs_About_Carbon-Carbon_Single_Bonds
Strain. (2012, June 20). Retrieved October 11, 2018 from http://www.chem.ucla.edu/~harding/notes/strain_01.pdf
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