THEORETICAL STUDIES OF POLYMORPHISM ON THIOUREA

DERIVATIVES; 1,3-BIS(4-FLUOROPHENYL)THIOUREA

Nur Najwa Alyani Mohd Nabil*1, Lee Sin Ang2

1, 2
Universiti Teknologi MARA Cawangan Perlis, Kampus Arau, MALAYSIA.
(E-mail: najwalyani90@yahoo.com, lsina2003@yahoo.com)

ABSTRACT

Same molecule found to be stable in more than one configuration is a crucial

phenomenon in various industries. This phenomenon, known as polymorphism may
cause changes in the physical properties of the compound, hence affecting their
usual usages. In this theoretical study, we embark on the aim to find the lowest
energy conformer of a flexible-type compound, 1,3-bis(4-fluorophenyl)thiourea.
This compound is a symmetrically substituted thiourea derivatives, where the
identical substituents exist on both sides of the HNCSNH. While most of other
symmetrically substituted thiourea derivative compounds had found to exhibit
polymorphism, previous experimental results of this compound show that the
substituents only adopt the cis-cis configuration as the most stable arrangement.
The calculations were performed using Gaussian 09 suite of program, with
B3LYP/DEF2-TZVP model chemistry. In order to assess the existence of another
lowest energy conformer, the substituents were rotated along the CN bond of the
molecules. The results show that, apart from its original configuration (cis-cis),
there exists another lowest configuration in the cis-trans configuration. Two
maxima exist on the potential energy surface in between these two stable
conformers. Based on the results, it may be concluded that this compound possesses
the ability to exist in another stable configuration, hence showing polymorphism.
However, this conclusion is based on the results of one-molecule system, where
interaction in a solid state environment is being neglected. Further works are being
performed in this direction to improve on the results.

Key word: Polymorphism, Thiourea, Conformer