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FINAL EXAM FORMAL REPORT

COMPUTATIONAL CHEMISTRY PRACTICUM


AMIDE ROTATION
ROTASI AMIDA

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

Wednesday, 23 May 2018


Assistant:

COMPUTATIONAL CHEMISTRY LABORATORIUM


FACULTY OF MATHEMATICS AND NATURAL SCIENCES
UNIVERSITAS GADJAH MADA
YOGYAKARTA
2018
RATIFICATION PAGE
FORMAL REPORT
AMIDE ROTATION

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:


23/05/2018

Yogyakarta, 23/05/18
Assistant, Practician,

Roma Karisti Silalahi


I. Objectives
To obtain the information regarding the rotation of the C-N bond on amide through the
use of semi-empirical AM1 method.

II. Theoretical Background


The internal rotation about the C-N bond in amides provides information in
understanding conformational characteristics of the backbone of peptides and proteins. The
barrier of amide bond increases as the polarity of hydrogen-bond ability of the solven
increases (Young, et al., 2004).
III. Discussion
a. Experimental Result
Molecule Torsion angle (°) Bond Energy (kcal/mol)
Dimethylformamide 20 -1086.941588
40 -1086.9472
60 -1086.9748
80 -1086.9271
100 -1086.959325
120 -1086.9525
140 -1086.9467
180 -1086.9757
Benzamide 20 -1749.7535
40 -1749.7616
60 -1749.7451
80 -1749.7492
100 -1749.7513
120 -1749.7545
140 -1749.7514
180 -1749.7510

b. Discussion
This experiment was conducted to obtain information regarding the C-N
bond strength of an amide using the semi-empirical AM1 method. The
experiment was done by the implementation of different angle torsion to four
different atoms within the compound with the same bondage. To the first
compound, dimethylformamide, it can be seen that the bond energy of each
angle has a very minimum difference. Whereas, for benzamide, the bond energy
for all the torsion angels are very similar, without any anomalies. When
comparing the two structures, overall, benzamide has a bigger bond energy for
all the torsion angles compared to dimethylformamide. This may be due to the
stearic groups contained within the benzamide, resulting in a larger bond energy
that only contains two from the methyl groups that are not equivalent to each
other.

IV. Conclusion
In comparison for the two structures analyzed, the compound that has the higher bond
energy for each and every torsion angle is benzamide.

V. References
Young, K. K., Park, H. S. 2004. Internal rotation about the C-N bond of amides. Journal of
Molecular Structure (Theochem), 676, 171-176, pp.
APPENDICES
Angle (°) Dimethylformamide Benzamide
20

40

60
80

100

120
140

180