3-[5-(4-Chloro-phen-yl)-1-(4-methoxy-phen-yl)-1H-pyrazol-3-yl]propionic acid and the corresponding methyl ester

Isuru R. Kumarasinghe, Victor J Hruby, Gary S. Nichol

Research output: Contribution to journalArticle

Abstract

The synthesis of 3-[5-(4-chloro-phen-yl)-1-(4-methoxy-phen-yl)-1H-pyrazol- 3-yl]propionic acid, C19H17ClN2O3, (I), and its corresponding methyl ester, methyl 3-[5-(4-chloro-phen-yl)-1-(4-methoxy-phen-yl)-1H-pyrazol-3-yl]propionate, C20H19ClN2O3, (II), is regiospecific. However, correct identification of the regioisomer formed by spectroscopic techniques is not trivial and single-crystal X-ray analysis provided the only means of unambiguous structure determination. Compound (I) crystallizes with Z′ = 2. The propionic acid groups of the two crystallographically unique mol-ecules form a hydrogen-bonded dimer, as is typical of carboxylic acid groups in the solid state. Conformational differences between the meth-oxy-benzene and pyrazole rings give rise to two unique mol-ecules. The structure of (II) features just one mol-ecule in the asymmetric unit and the crystal packing makes greater use than (I) of weak C - H⋯A inter-actions, despite the lack of any functional groups for classical hydrogen bonding.

Original languageEnglish (US)
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume65
Issue number4
DOIs
StatePublished - 2009

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Esters
Propionates
X ray analysis
Hydrogen Bonding
Carboxylic Acids
Benzene
Dimers
Functional groups
Hydrogen
Hydrogen bonds
X-Rays
Single crystals
Crystals
propionic acid
pyrazole

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)

Cite this

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title = "3-[5-(4-Chloro-phen-yl)-1-(4-methoxy-phen-yl)-1H-pyrazol-3-yl]propionic acid and the corresponding methyl ester",
abstract = "The synthesis of 3-[5-(4-chloro-phen-yl)-1-(4-methoxy-phen-yl)-1H-pyrazol- 3-yl]propionic acid, C19H17ClN2O3, (I), and its corresponding methyl ester, methyl 3-[5-(4-chloro-phen-yl)-1-(4-methoxy-phen-yl)-1H-pyrazol-3-yl]propionate, C20H19ClN2O3, (II), is regiospecific. However, correct identification of the regioisomer formed by spectroscopic techniques is not trivial and single-crystal X-ray analysis provided the only means of unambiguous structure determination. Compound (I) crystallizes with Z′ = 2. The propionic acid groups of the two crystallographically unique mol-ecules form a hydrogen-bonded dimer, as is typical of carboxylic acid groups in the solid state. Conformational differences between the meth-oxy-benzene and pyrazole rings give rise to two unique mol-ecules. The structure of (II) features just one mol-ecule in the asymmetric unit and the crystal packing makes greater use than (I) of weak C - H⋯A inter-actions, despite the lack of any functional groups for classical hydrogen bonding.",
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T1 - 3-[5-(4-Chloro-phen-yl)-1-(4-methoxy-phen-yl)-1H-pyrazol-3-yl]propionic acid and the corresponding methyl ester

AU - Kumarasinghe, Isuru R.

AU - Hruby, Victor J

AU - Nichol, Gary S.

PY - 2009

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N2 - The synthesis of 3-[5-(4-chloro-phen-yl)-1-(4-methoxy-phen-yl)-1H-pyrazol- 3-yl]propionic acid, C19H17ClN2O3, (I), and its corresponding methyl ester, methyl 3-[5-(4-chloro-phen-yl)-1-(4-methoxy-phen-yl)-1H-pyrazol-3-yl]propionate, C20H19ClN2O3, (II), is regiospecific. However, correct identification of the regioisomer formed by spectroscopic techniques is not trivial and single-crystal X-ray analysis provided the only means of unambiguous structure determination. Compound (I) crystallizes with Z′ = 2. The propionic acid groups of the two crystallographically unique mol-ecules form a hydrogen-bonded dimer, as is typical of carboxylic acid groups in the solid state. Conformational differences between the meth-oxy-benzene and pyrazole rings give rise to two unique mol-ecules. The structure of (II) features just one mol-ecule in the asymmetric unit and the crystal packing makes greater use than (I) of weak C - H⋯A inter-actions, despite the lack of any functional groups for classical hydrogen bonding.

AB - The synthesis of 3-[5-(4-chloro-phen-yl)-1-(4-methoxy-phen-yl)-1H-pyrazol- 3-yl]propionic acid, C19H17ClN2O3, (I), and its corresponding methyl ester, methyl 3-[5-(4-chloro-phen-yl)-1-(4-methoxy-phen-yl)-1H-pyrazol-3-yl]propionate, C20H19ClN2O3, (II), is regiospecific. However, correct identification of the regioisomer formed by spectroscopic techniques is not trivial and single-crystal X-ray analysis provided the only means of unambiguous structure determination. Compound (I) crystallizes with Z′ = 2. The propionic acid groups of the two crystallographically unique mol-ecules form a hydrogen-bonded dimer, as is typical of carboxylic acid groups in the solid state. Conformational differences between the meth-oxy-benzene and pyrazole rings give rise to two unique mol-ecules. The structure of (II) features just one mol-ecule in the asymmetric unit and the crystal packing makes greater use than (I) of weak C - H⋯A inter-actions, despite the lack of any functional groups for classical hydrogen bonding.

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