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    Exercise 22 - Hyperchem 8 04 MM Calculations Energy of Rotation Round Single Bonds

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    The document describes a study that rotated the ethenyl group of an ethenyl pyrrole molecule around its single bond to the pyrrole ring in 5 degree increments and recorded the energies. A graph of the energy values showed that the lowest energies occurred when the ethenyl group was rotated 180 degrees or 270 degrees from its original position. These conformations allowed for favorable double bond conjugation throughout the molecule as well as interaction between the ethenyl group's pi bonds and the nitrogen atom's orbitals, lowering the energy.

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    Exercise 22 - Hyperchem 8 04 MM Calculations Energy of Rotation Round Single Bonds

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    The document describes a study that rotated the ethenyl group of an ethenyl pyrrole molecule around its single bond to the pyrrole ring in 5 degree increments and recorded the energies. A graph of the energy values showed that the lowest energies occurred when the ethenyl group was rotated 180 degrees or 270 degrees from its original position. These conformations allowed for favorable double bond conjugation throughout the molecule as well as interaction between the ethenyl group's pi bonds and the nitrogen atom's orbitals, lowering the energy.

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    The document describes a study that rotated the ethenyl group of an ethenyl pyrrole molecule around its single bond to the pyrrole ring in 5 degree increments and recorded the energies. A graph of the energy values showed that the lowest energies occurred when the ethenyl group was rotated 180 degrees or 270 degrees from its original position. These conformations allowed for favorable double bond conjugation throughout the molecule as well as interaction between the ethenyl group's pi bonds and the nitrogen atom's orbitals, lowering the energy.

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    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
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    189 views5 pages

    Exercise 22 - Hyperchem 8 04 MM Calculations Energy of Rotation Round Single Bonds

    Uploaded by

    api-235187189
    The document describes a study that rotated the ethenyl group of an ethenyl pyrrole molecule around its single bond to the pyrrole ring in 5 degree increments and recorded the energies. A graph of the energy values showed that the lowest energies occurred when the ethenyl group was rotated 180 degrees or 270 degrees from its original position. These conformations allowed for favorable double bond conjugation throughout the molecule as well as interaction between the ethenyl group's pi bonds and the nitrogen atom's orbitals, lowering the energy.

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    © All Rights Reserved
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    of 5

    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.

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