FORMAL REPORT

COMPUTATIONAL CHEMISTRY PRACTICUM

CYCLOHEXANE ANALYSIS
ANALISIS SIKLOHEKSANA

By :
Roma Karisti Silalahi
15/386858/PA/17054

Wednesday, 21 February 2018

Assistant:

COMPUTATIONAL CHEMISTRY LABORATORIUM

FACULTY OF MATHEMATICS AND NATURAL SCIENCES
UNIVERSITAS GADJAH MADA
YOGYAKARTA
2018
 RATIFICATION PAGE
FORMAL REPORT
CYCLOHEXANE ANALYSIS

This laboratory work report has been prepared and created by:

ROMA KARISTI SILALAHI

15/386858/PA/17054

and has been checked by the assistant on:

05/03/2018

Yogyakarta, 05/03/18
Assistant, Practician,

Roma Karisti Silalahi

I. Objectives
Determine the most stable cyclohexane conformation using AMBER gravitational field
calculation.

II. Theoretical Background

Cyclohexane rings, either singly or in an integrated ring system (fused-ring system, ring
systems with a strength of carbon atoms) are the most important ring systems. If the
cyclohexane ring is flat, then all the hydrogen atoms on the carbon ring carbon will be
cascaded. But in a folded conformer, all hydrogen is shaky. Conformer energy folds of
cyclohexane are lower than flat cyclohexane energies, since sp3 bond angles are more
reasonable and also because rejects reject smaller hydrogens.
A cyclohexane ring may have many forms, and any single cyclohexane molecule
continues to be in a state of bending into various shapes (molecular models are most useful
in relating these conformations) so far only cyclohexane chair have been introduced. None
of the other conformations have the desired rocking hydrogen structure, such as the structure
of the seat form (conformation). Hydrogen eclipse as in the form of a bolt, adding molecular
energy. Energy requirements for the interconversion (inter-change) conformational
conformation of cyclohexane are shown in the following figure:

Figure II.1: Interconversion energy of cyclohexane conformations

Seen from the picture that the shape of the seat has the lowest energy, while the form of
half-seats (which has almost flat structure) has the highest energy. It can be estimated that
most cyclohexane molecules form seats at any time. It has been calculated that about 99.9%
 of the cyclohexane molecules are in seats at any time (Fessenden, 2006).

III. Discussion
In this experiment, the most stable conformation of cyclohexane was determined using
AMBER-style field calculations. The most stable determination of conformation will be
seen from the conformational energy contained in each conformation. From the experiment
conducted got the following results:
Torsion Angle Energy
Conformation Distance CC (Å) Angle CCC (˚) CCCC (˚) (kcal/mol)
Chair 1.53577 111.241 55.3799 5.7016
Boat 1.54214 113.739 7.41E-11 13.041986
Intermediate
(twisted boat) 1.54112 113.891 29.36 12.280711

The data is drawn from the optimized conformation structure using Amber-style field
calculations. In accordance with existing theory, the energy possessed by cyclohexane in
the form of a seat has the lowest energy compared with other forms of conformation. This
is because each carbon ring of cyclohexane binds two hydrogen atoms in two distinct
positions, axial hydrogen and equatorial hydrogen, each of these hydrogens when facing
each other will of course have a standoff between the hydrogen of each other, and from the
conformational structure that there is, the seat shape provides a position that has the lowest
hydrogen in sight so that the energy it has is the smallest. In contrast to the shape of the boat
and the shape of the twist that hydrogen positions more face to face so decreases the energy
repulsion that makes it become unstable.
When viewed from other data, the distance between the atoms CC and the angle formed
from the CCC atom no significant difference because the position C does not change in the
extreme. The difference is quite noticeable at the CCCC torque angle formed from the 4 C
atoms that make up the conformation shape, when viewed from the shape each of them has
a different shape between the shape of the seat, the boat and the twist, hence when calculated
the angle of torque between 4 C. Such conformations will be different from each other.
It is also known that the distance between H flagpole or H axial position is closest to
each other in the form of each conformation. In boat form before optimized distance of H
flagpole equal to 2,10232 Å while after optimized to 2,4374 Å. In the form of a twist before
the H flagpole is optimized distance of 2.38402 Å while optimized to 2.66762 Å. From the
data obtained, it is clear that there is a change of position after the structure is optimized
using AMBER force field calculation. The distance between H flagpole further indicates
that the optimized structure has an H distance that is too close so that the energy generated
is greater than the energy after it is optimized. As the distance H goes further is bound to be
followed by the smaller conformational energy, this indicates that the axial H spacing plays
an important role in the energy generated, therefore the less distance the H is facing and the
farther the position the cyclohexane will be much more stable and has low energy. From
the energy data conformation obtained can be calculated relative energy for each
conformation, which is as follows:
Chair Boat Twist
Absolute AMBER energy (kcal/mol) 5.7016 13.041986 12.280711
Relative AMBER energy (kcal/mol) 0 7.340386 6.579111

It can be seen that the energy of the smallest form of the seat and the shape of the
largest boat, so that the most stable seat shape and the most unstable boat shape. In the
event of a conformational change from one form to another it will require energy called
interconversion energy. The energy needed for change to change the shape can be seen
from the difference in energy held between the form as the following diagram:
IV. Conclusion
Thus, the conformation of the most stable cyclohexane is the seat form with a
conformational energy of 5.7016 kcal/mol smaller than the other conformational energy
when calculated using AMBER force field calculations.

V. Daftar Pustaka
Dean, John A., 1999, Lange’s Handbook of Chemistry, Mc Graw – Hill, Inc, New York.
Fessenden, R.J., dan Fessenden, J.S., 1986, Kimia Organik, Jilid 1, Erlangga, Jakarta.
McMurry J., 2012, Organic Chemistry, Eight Edition, Brooks/Cole Publishing Company,
California.
 APPENDICES
Chair conformation:

Boat conformation:

Twist conformation: