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