Origin of the Thermodynamic Stability of the Polymorph IV of Crystalline Barbituric Acid: Evidence from Solid-State NMR and Electron Density Analyses

BADRI, Zahra, Kateřina BOUZKOVÁ, Cina FOROUTANNEJAD and Radek MAREK. Origin of the Thermodynamic Stability of the Polymorph IV of Crystalline Barbituric Acid: Evidence from Solid-State NMR and Electron Density Analyses. Crystal Growth & Design. Washington, DC: American Chemical Society, 2014, vol. 14, No 6, p. 2763-2772. ISSN 1528-7483. Available from: https://dx.doi.org/10.1021/cg401899q.

Basic information

• Original name: Origin of the Thermodynamic Stability of the Polymorph IV of Crystalline Barbituric Acid: Evidence from Solid-State NMR and Electron Density Analyses
• Authors: BADRI, Zahra (364 Islamic Republic of Iran, belonging to the institution), Kateřina BOUZKOVÁ (203 Czech Republic, belonging to the institution), Cina FOROUTANNEJAD (364 Islamic Republic of Iran, belonging to the institution) and Radek MAREK (203 Czech Republic, guarantor, belonging to the institution).
• Edition: Crystal Growth & Design, Washington, DC, American Chemical Society, 2014, 1528-7483.

Other information

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 10403 Physical chemistry
• Country of publisher: United States of America
• Confidentiality degree: is not subject to a state or trade secret
• WWW: DOI: 10.1021/cg401899q
• Impact factor: Impact factor: 4.891
• RIV identification code: RIV/00216224:14740/14:00073614
• Organization unit: Central European Institute of Technology
• Doi: http://dx.doi.org/10.1021/cg401899q
• UT WoS: 000337018900012
• Keywords in English: polymorph; cluster; NMR chemical shift tensor; delocalization index; intermolecular interaction; hydrogen bonding; stacking
• Tags: kontrola MP, podil, rivok
• Tags: International impact, Reviewed

Abstract

In this contribution, the origin of the stability of the polymorph IV (enol form) of crystalline barbituric acid relative to the polymorph II (keto form) is investigated using solid-state NMR spectroscopy and electron density analysis. Electron density analysis reveals differences in the nature of the intermolecular contacts in the different polymorphs of barbituric acid. Comparing the properties of hypothetical single molecules of barbituric acid with cluster models shows that the electronic and magnetic properties of polymorphs of barbituric acid can be employed to measure the strengths of the intermolecular interactions. Changes in the magnitudes of the NMR chemical shift tensors are also shown to be parallel to the intermolecular QTAIM delocalization index, which measures the covalency of an intermolecular interaction.

Links

• ED1.1.00/02.0068, research and development project: Name: CEITEC - central european institute of technology
• EE2.3.30.0009, research and development project: Name: Zaměstnáním čerstvých absolventů doktorského studia k vědecké excelenci
• GAP206/11/0550, research and development project: Name: NMR spektroskopie pevného stavu organických molekul, polymorfů, solvátů a komplexů (Acronym: ssNMR)

Investor: Czech Science Foundation