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Hydrogen bonding interactions in E- or Z-2-phenyl-3-(X'-pyridyl)propenoic acid (X=2, 3 or 4) assemblies - A molecular modeling study

Csehi, József and Pálinkó, István (2004) Hydrogen bonding interactions in E- or Z-2-phenyl-3-(X'-pyridyl)propenoic acid (X=2, 3 or 4) assemblies - A molecular modeling study. JOURNAL OF MOLECULAR MODELING, 10 (2). pp. 151-154. ISSN 1610-2940

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Abstract

The agglomeration properties of stereoisomeric 2-phenyl-3-(X'-pyridyl)propenoic acids (X=2, 3 or 4) were studied by the PM3 semiempirical quantum chemical method. Calculations revealed that dimers kept together by the intermolecular hydrogen bonding interactions of the carboxylic groups could be built from both stereoisomers irrespective of the position of the nitrogen heteroatom. The dimers of the Z-isomers could also be built through (aromatic)C-H...N hydrogen bonds between the dimer units. The longest agglomerate was the pentamer of the dimers when the nitrogen was in the 2' position. Longer hydrogen-bonded agglomerates than dimers could only be constructed from the E-isomer with the nitrogen in position 4'. Here, the trimer of the dimers proved to be the longest hydrogen-bonded entity and similarly to the Z-isomers, the dimer units are kept together by (aromatic)C-H...N intermolecular hydrogen bonds.

Item Type: Article
Subjects: Q Science / természettudomány > QA Mathematics / matematika > QA75 Electronic computers. Computer science / számítástechnika, számítógéptudomány
Q Science / természettudomány > QD Chemistry / kémia
Q Science / természettudomány > QH Natural history / természetrajz > QH301 Biology / biológia > QH3011 Biochemistry / biokémia
Q Science / természettudomány > QH Natural history / természetrajz > QH301 Biology / biológia > QH3015 Molecular biology / molekuláris biológia
Q Science / természettudomány > QH Natural history / természetrajz > QH301 Biology / biológia > QH3020 Biophysics / biofizika
SWORD Depositor: MTMT SWORD
Depositing User: MTMT SWORD
Date Deposited: 31 May 2013 10:36
Last Modified: 31 May 2013 10:36
URI: http://real.mtak.hu/id/eprint/5412

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