Exercise 22 - HyperChem 8.

04 MM Calculations - Energy of Rotation round Single Bonds

Theoretical Organic Chemistry, 2013
Anastazija Ristovska

Figure 1: Ethenyl Pyrrole Structural Balls-and-Sticks Representation

Were going to rotate the ethenyl group around the single bond that attaches it to the pyrrole ring, and
record the energies as we change the angle of rotation by 5 degrees at a time. From the energy values
obtained were going to construct a graph plot, and determine the angle of the ethenyl group is oriented
to the pyrrole ring at the lowest energy cost.
All calculations, molecular models, and data were obtained using the HyperChem v.8.04 Software.

Figure 2: Ethenyl Pyrrole Structural Balls-and-Sticks Representation - We have Selected the Ethenyl Group and now
we're going to rotate it around its single bond.

Angle of
Rotation ()

Energy
(kcal/mol)

115

15,72

240

15,39

120

15,39

245

15,72

12,3

125

15,02

250

16,01

12,33

130

14,63

255

16,25

10

12,42

135

14,23

260

16,43

15

12,58

140

13,83

265

16,55

20

12,79

145

13,44

270

16,59

25

13,06

150

13,09

275

16,57

30

13,36

155

12,76

280

16,48

35

13,7

160

12,49

285

16,32

40

14,06

165

12,26

290

16,11

45

14,44

170

12,1

295

15,84

50

14,82

175

12

300

15,53

55

15,18

180

11,96

305

15,18

60

15,53

185

12

310

14,82

65

15,84

190

12,1

315

14,44

70

16,11

195

12,26

320

14,06

75

16,32

200

12,49

325

13,7

80

16,48

205

12,76

330

13,36

85

16,57

210

13,09

335

13,06

90

16,59

215

13,44

340

12,79

95

16,55

220

13,83

345

12,58

100

16,43

225

14,23

350

12,42

105

16,25

230

14,63

355

12,33

110

16,01

235

15,02

360

12,3

Figure 3: Ethenyl Group Rotated around

Single Bond for 30 degrees

Figure 4: Ethenyl Group Rotated around

Single Bond for 60 degrees

Figure 5: Ethenyl Group Rotated around

Single Bond for 90 degrees
Figure 8: Ethenyl Group Rotated around
Single Bond for 180 degrees

Figure 6: Ethenyl Group Rotated around

Single Bond for 120 degrees

Figure 9: Ethenyl Group Rotated around

Single Bond for 210 degrees

Figure 7: Ethenyl Group Rotated around

Single Bond for 150 degrees
Figure 10: Ethenyl Group Rotated around
Single Bond for 240 degrees

Figure 11: Ethenyl Group Rotated around

Single Bond for 270 degrees

Figure 13: Ethenyl Group Rotated around

Single Bond for 330 degrees

Figure 14: Ethenyl Group Rotated around

Single Bond for 360 degrees

Figure 12: Ethenyl Group Rotated around

Single Bond for 300 degrees

90; 16,59
kcal/mol

16,8

270;
16,59kcal/mol

Energy (kcal/mol)

15,8

14,8

13,8

12,8

180;
11,96kcal/mol

11,8
0

50

100

150

200

250

360; 12,3kcal/mol
300

350

400

Degree of Rotation ()

When rotated by 180 from its original position, the

molecule hit lowest energy. Even though the original
position of the ethenyl group was favorable for double
bonds conjugation throughout the molecule, the 180
rotated ethenyl group, in addition to favorable
conformation for the formation of double bonds
conjugation throughout the entire molecule, also
provided -bonds and molecular orbitals space from the
ethenyl group for the electron density of the nitrogen
atom, and vice-versa, the nitrogen atom provided empty
p atomic orbitals for stabilizing the electron density of
the double bond approaching it.