Crystal polymorphism and spectroscopical properties of sulfonamides in solid state by means of First Principles calculations

Abstract

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.

Insight into the Structure and Property Diversity of Four Nicorandil Oxalate Salt Polymorphs Based on Experiments and Quantum Chemistry Study

“…Quantum chemical studies on crystal polymorphism increased rapidly with the improvement in computer technology. − Beran et al presented the crystal energy landscape of ROY by intramolecular conformational energy and crystal energy calculation. Malec et al used Born–Oppenheimer molecular dynamics to explore the disappearance of the thermodynamically stable form of urea-barbituric acid cocrystal.…”

“…Other property differences such as color can also be explained through quantum chemical study. 28 Quantum chemical study provided a new route to understand the relationship between crystal structure and physicochemical property in polymorphism. 32,33 In this work, four polymorphs of NIC-OA salt were first prepared through ethanol/water solution crystallization.…”

“…Furthermore, Prado et al analyzed the electronic structure of Carvedilol polymorphs’ crystal faces and pointed out that differences between crystal surfaces would change the crystal habit in the solvent, which in turn would alter the dissolution rates. Other property differences such as color can also be explained through quantum chemical study . Quantum chemical study provided a new route to understand the relationship between crystal structure and physicochemical property in polymorphism. , …”

Conformational Stability and Vibrational Relaxation as a Function of Halogen Substitution in Benzene sulfonamides: A Theoretical Study

“…BSA are a class of compounds that are of great interest in the biochemical field since they are effective against a wide range of diseases. [60][61][62][63][64][65][66][67][68][69][70][71][72][73][74][75][76][77] Derivatives are used as medications to inhibit the formation of carbonic acid by the carbonic anhydrase enzyme. According to a recent study, [78] an inhibitor ligand's ability to adopt the proper shape to fit into the target binding site impacts both the strength of the effect and how well it binds to the target.…”

“…BSA are a class of compounds that are of great interest in the biochemical field since they are effective against a wide range of diseases [60–77] . Derivatives are used as medications to inhibit the formation of carbonic acid by the carbonic anhydrase enzyme.…”