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

J 2014

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 a Radek MAREK

Základní údaje

Originální název

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

Autoři

BADRI, Zahra (364 Írán, domácí), Kateřina BOUZKOVÁ (203 Česká republika, domácí), Cina FOROUTANNEJAD (364 Írán, domácí) a Radek MAREK (203 Česká republika, garant, domácí)

Vydání

Crystal Growth & Design, Washington, DC, American Chemical Society, 2014, 1528-7483

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10403 Physical chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

DOI: 10.1021/cg401899q

Impakt faktor

Impact factor: 4.891

Kód RIV

RIV/00216224:14740/14:00073614

Organizační jednotka

Středoevropský technologický institut

DOI

http://dx.doi.org/10.1021/cg401899q

UT WoS

000337018900012

Klíčová slova anglicky

polymorph; cluster; NMR chemical shift tensor; delocalization index; intermolecular interaction; hydrogen bonding; stacking

Štítky

kontrola MP, podil, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 7. 11. 2014 17:30, prof. RNDr. Radek Marek, Ph.D.

Anotace

V originále

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.

Návaznosti

ED1.1.00/02.0068, projekt VaV

Název: CEITEC - central european institute of technology

EE2.3.30.0009, projekt VaV

Název: Zaměstnáním čerstvých absolventů doktorského studia k vědecké excelenci

GAP206/11/0550, projekt VaV

Název: NMR spektroskopie pevného stavu organických molekul, polymorfů, solvátů a komplexů (Akronym: ssNMR)

Investor: Grantová agentura ČR, NMR spektroskopie pevného stavu organických molekul, polymorfů, solvátů a komplexů

Přiložené soubory

CGD14_14_2763_cg401899q.pdf

Požádat o autorskou verzi souboru

Citovat

BADRI, Zahra, Kateřina BOUZKOVÁ, Cina FOROUTANNEJAD a 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, roč. 14, č. 6, s. 2763-2772. ISSN 1528-7483. Dostupné z: https://dx.doi.org/10.1021/cg401899q.

@article{1182117,
   author = {Badri, Zahra and Bouzková, Kateřina and Foroutannejad, Cina and Marek, Radek},
   article_location = {Washington, DC},
   article_number = {6},
   doi = {http://dx.doi.org/10.1021/cg401899q},
   keywords = {polymorph; cluster; NMR chemical shift tensor; delocalization index; intermolecular interaction; hydrogen bonding; stacking},
   language = {eng},
   issn = {1528-7483},
   journal = {Crystal Growth & Design},
   title = {Origin of the Thermodynamic Stability of the Polymorph IV of Crystalline Barbituric Acid: Evidence from Solid-State NMR and Electron Density Analyses},
   url = {http://dx.doi.org/10.1021/cg401899q},
   volume = {14},
   year = {2014}
}

TY  - JOUR
ID  - 1182117
AU  - Badri, Zahra - Bouzková, Kateřina - Foroutannejad, Cina - Marek, Radek
PY  - 2014
TI  - Origin of the Thermodynamic Stability of the Polymorph IV of Crystalline Barbituric Acid: Evidence from Solid-State NMR and Electron Density Analyses
JF  - Crystal Growth & Design
VL  - 14
IS  - 6
SP  - 2763-2772
EP  - 2763-2772
PB  - American Chemical Society
SN  - 15287483
KW  - polymorph
KW  - cluster
KW  - NMR chemical shift tensor
KW  - delocalization index
KW  - intermolecular interaction
KW  - hydrogen bonding
KW  - stacking
UR  - http://dx.doi.org/10.1021/cg401899q
L2  - http://dx.doi.org/10.1021/cg401899q
N2  - 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.
ER  -

BADRI, Zahra, Kateřina BOUZKOVÁ, Cina FOROUTANNEJAD a Radek MAREK. Origin of the Thermodynamic Stability of the Polymorph IV of Crystalline Barbituric Acid: Evidence from Solid-State NMR and Electron Density Analyses. \textit{Crystal Growth \&{} Design}. Washington, DC: American Chemical Society, 2014, roč.~14, č.~6, s.~2763-2772. ISSN~1528-7483. Dostupné z: https://dx.doi.org/10.1021/cg401899q.

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