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 language | English (US) |
|---|---|
| Journal | Acta Crystallographica Section C: Crystal Structure Communications |
| Volume | 65 |
| Issue number | 4 |
| DOIs | |
| State | Published - 2009 |
Fingerprint
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
Cite this
3-[5-(4-Chloro-phen-yl)-1-(4-methoxy-phen-yl)-1H-pyrazol-3-yl]propionic acid and the corresponding methyl ester. / Kumarasinghe, Isuru R.; Hruby, Victor J; Nichol, Gary S.
In: Acta Crystallographica Section C: Crystal Structure Communications, Vol. 65, No. 4, 2009.Research output: Contribution to journal › Article
}
TY - JOUR
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
Y1 - 2009
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.
UR - http://www.scopus.com/inward/record.url?scp=64249110195&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=64249110195&partnerID=8YFLogxK
U2 - 10.1107/S010827010900941X
DO - 10.1107/S010827010900941X
M3 - Article
VL - 65
JO - Acta Crystallographica Section C: Crystal Structure Communications
JF - Acta Crystallographica Section C: Crystal Structure Communications
SN - 0108-2701
IS - 4
ER -