Abstract
Intramolecular hydrogen bonding interactions were searched for in conformers of isolated α-phenyl-, α-pyridyl- and α-furylcinnamic acid stereoisomers. The conformers were obtained by ab initio (HF/3-21G//HF/3-21G and HF/6-31G(d,p)//HF/6-31G(d,p)) quantum chemical methods using initial geometries corresponding to the global minima determined at the level of semi-empirical quantum chemical calculations. The most common intramolecular hydrogen bond was of C-H...O type. In certain conformers of α-(2-pyridyl)cinnamic acids, O-H...Npyridyl and α-(2-furyl)cinnamic acids, O-H...Ofuryl interactions were also found. In most cases, at the level of HF/3-21G calculations, these conformers were more stable than those lacking these close contacts. When the larger basis set was applied the extra stabilizing effect disappeared, nevertheless, these geometries still represented minimum structures.
| Original language | English |
|---|---|
| Pages (from-to) | 139-149 |
| Number of pages | 11 |
| Journal | Journal of Molecular Structure: THEOCHEM |
| Volume | 535 |
| DOIs | |
| State | Published - Jan 15 2001 |
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All Science Journal Classification (ASJC) codes
- Physical and Theoretical Chemistry
- Computational Theory and Mathematics
- Atomic and Molecular Physics, and Optics
Cite this
Intramolecular hydrogen bonding in α-phenylcinnamic acids and their heteroatom-containing derivatives studied by ab initio quantum chemical methods. / Körtvélyesi, T.; Kukovecz, Á; Lovas, Sándor; Pálinkó, I.
In: Journal of Molecular Structure: THEOCHEM, Vol. 535, 15.01.2001, p. 139-149.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Intramolecular hydrogen bonding in α-phenylcinnamic acids and their heteroatom-containing derivatives studied by ab initio quantum chemical methods
AU - Körtvélyesi, T.
AU - Kukovecz, Á
AU - Lovas, Sándor
AU - Pálinkó, I.
PY - 2001/1/15
Y1 - 2001/1/15
N2 - Intramolecular hydrogen bonding interactions were searched for in conformers of isolated α-phenyl-, α-pyridyl- and α-furylcinnamic acid stereoisomers. The conformers were obtained by ab initio (HF/3-21G//HF/3-21G and HF/6-31G(d,p)//HF/6-31G(d,p)) quantum chemical methods using initial geometries corresponding to the global minima determined at the level of semi-empirical quantum chemical calculations. The most common intramolecular hydrogen bond was of C-H...O type. In certain conformers of α-(2-pyridyl)cinnamic acids, O-H...Npyridyl and α-(2-furyl)cinnamic acids, O-H...Ofuryl interactions were also found. In most cases, at the level of HF/3-21G calculations, these conformers were more stable than those lacking these close contacts. When the larger basis set was applied the extra stabilizing effect disappeared, nevertheless, these geometries still represented minimum structures.
AB - Intramolecular hydrogen bonding interactions were searched for in conformers of isolated α-phenyl-, α-pyridyl- and α-furylcinnamic acid stereoisomers. The conformers were obtained by ab initio (HF/3-21G//HF/3-21G and HF/6-31G(d,p)//HF/6-31G(d,p)) quantum chemical methods using initial geometries corresponding to the global minima determined at the level of semi-empirical quantum chemical calculations. The most common intramolecular hydrogen bond was of C-H...O type. In certain conformers of α-(2-pyridyl)cinnamic acids, O-H...Npyridyl and α-(2-furyl)cinnamic acids, O-H...Ofuryl interactions were also found. In most cases, at the level of HF/3-21G calculations, these conformers were more stable than those lacking these close contacts. When the larger basis set was applied the extra stabilizing effect disappeared, nevertheless, these geometries still represented minimum structures.
UR - http://www.scopus.com/inward/record.url?scp=0035862891&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0035862891&partnerID=8YFLogxK
U2 - 10.1016/S0166-1280(00)00588-1
DO - 10.1016/S0166-1280(00)00588-1
M3 - Article
AN - SCOPUS:0035862891
VL - 535
SP - 139
EP - 149
JO - Computational and Theoretical Chemistry
JF - Computational and Theoretical Chemistry
SN - 2210-271X
ER -