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https://doi.org/10.5562/cca3346

Experimental Charge Density Analysis of the Anti-inflammatory Drug Meloxicam [sodium 4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxamide Monohydrate]

Niranjana Devi Rajendran ; Department of Physics, Fatima College, Madurai, Tamil Nadu, India
Arputharaj David Stephen ; Department of Physics, Sri Shakthi Institute of Engineering and Technology, Coimbatore, Tamil Nadu, India
Christian Jelsch ; CRM2, UNR CNRS 7036, Institut Jean Barriol, Université de Lorraine, Vandoeuvre les Nancy cedex, France
Eduardo C. Escudero-Adán ; The Barcelona Institute of Science and Technology, Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16 - 43007 Tarragona, Spain


Puni tekst: engleski pdf 8.220 Kb

str. 221-232

preuzimanja: 787

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Sažetak

The charge density analysis of meloxicam sodium monohydrate [sodium 4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxamide monohydrate] was performed with high-resolution X-ray diffraction data measured at low temperature (90 K). The experimental results were compared with those derived from the corresponding periodic theoretical calculations at the B3LYP/6-31G** level of theory. The multipolar charge-density analysis highlights the regions of meloxicam which are the most electronegative. These regions correspond to those forming short electrostatic interactions with the Na+ cation.
The molecular conformation in the crystal is maintained by a strong intramolecular N−H…O=C hydrogen bond. The Na+ cation interacts with as much as five neighboring oxygen atoms. The strong hydrogen bonds N/O−H…O/N, the Na…O short contacts and hydrophobic aromatic stacking between the two aromatic cycles constitute the most represented and enriched contact types and act as the driving force in the crystal packing formation. The crystal packing presents several meloxicam anion dimers but also one Na+…Na+ repulsive interactions which are largely compensated by the electrostatic favorable attractions between anions and cations.

This work is licensed under a Creative Commons Attribution 4.0 International License.

Ključne riječi

meloxicam; X-ray crystallography; quantum calculation; electron density; topological analysis; electrostatic potential; interaction energy

Hrčak ID:

202769

URI

https://hrcak.srce.hr/202769

Datum izdavanja:

4.6.2018.

Posjeta: 1.279 *