Crystal polymorphism and spectroscopical properties of sulfonamides in solid state by means of First Principles calculations
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Springer
Materia
Sulfonamides Polymorphism DFT calculations Infrared spectroscopy Hydrogen bonds
Date
2022-07-26Referencia bibliográfica
Sainz-Díaz, C.I... [et al.]. Crystal polymorphism and spectroscopical properties of sulfonamides in solid state by means of First Principles calculations. J Comput Aided Mol Des 36, 549–562 (2022). [https://doi.org/10.1007/s10822-022-00465-2]
Sponsorship
EU Framework Program Horizon 2020 CA17120; Andalusian project P18-RT-3786; Secretaria de Educacion, Ciencia, Tecnologia e Innovacion (SECTEI) of the Mexico City PAPIIT-IN230419Abstract
Sulfonamides are an important class of therapeutic agents. The increase in the number of new sulfonamide derivatives makes
it necessary to study more rationally the chemical structure, because the solid forms often display different mechanical,
thermal and physicochemical properties that can influence the bioavailability and stability of the drugs; consequently, the
polymorphic structures are of great interest to the pharmaceutical industry because of their ability to modify the physical
properties of the active pharmaceutical ingredient. The molecular interactions of these drugs in their crystal lattice are
important for the stability of the crystals and polymorphism and for preparing composite complexes for optimizing the use of
these drugs. In this work, the crystal structure of these drugs and crystal polymorphism is investigated. So, the crystal forms
of antibiotics derivatives of the sulfonamides, sulfamethoxazole, sulfamethazine, sulfachloropyridazine, and sulfacetamide
are studied at the molecular and supramolecular level by using computational modeling approach at quantum mechanical
level. The spectroscopic properties of these systems are also studied explaining assignments of previous experimental data.
The results of DFT calculations reproduce the crystal structures of sulfonamides determined experimentally and the polymorphism
in these molecules have been clarified. Likewise, the main intermolecular interactions in all crystal forms of these
sulfonamides are H-bonds among the sulfonic and amino groups and SNH groups, and also some π-π interactions. Also,
these 3-D periodical models allow the exploration of the intermolecular interactions included in the crystal structures and
some of these interactions can alter the vibration modes of the molecules. Therefore, the use of these models can be useful
for experimental spectroscopy studies where use actual crystal solids.