INQUINOA   21218
INSTITUTO DE QUIMICA DEL NOROESTE
Unidad Ejecutora - UE
artículos
Título:
Structural and vibrational study of 2-(2- furyl)-1h-imidazole
Autor/es:
A. E. LEDESMA; S. A. BRANDÁN; J. ZINCZUK; O. E. PIRO; J. J. LÓPEZ- GONZÁLEZ; A. BEN ALTABEF
Revista:
J. Phys. Org. Chem.
Editorial:
Wiley & Sons, Ltd.
Referencias:
Año: 2008 vol. 21 p. 1086 - 1097
Resumen:
The 2-(2(-furyl)-1H-imidazole (1) has been prepared and characterized using infrared, Raman, and multidimensional
nuclear magnetic resonance spectroscopies. Two conformations of this species obtained by rotation of 1808,
approximately, around the CC inter-ring bond are detected. Likewise, the crystal and molecular structure of 1
has been analyzed by X-ray diffraction methods and it evidenced that both conformations are present in the lattice
with equal occupancy and linked in alternate way to the NH---N bonded polymeric chains along the crystal [101]
direction. Theoretical calculations have been carried out by employing the density functional theory (DFT)/B3LYP
method, in order to optimize the geometry in gas phase of both conformers and to support the assignments of the
vibrational bands of 1 to their normal modes. For a complete assignment of the compound, DFT calculations were
combined with Pulays SQMFF methodology in order to fit the theoretical frequency values to the experimental one.
The nuclear magnetic resonance spectrum observed for 1 is successfully compared with the calculated chemicals shifts
at B3LYP/6-311þþG** level of theory for the two conformers. Furthermore, natural bond orbital (NBO) analysis and
topological (AIM) calculations for an oligomer, containing three alternated units of the NH---N bonded chain found
in the crystal, reveals the characteristics of the hydrogen bonds present in the polymeric structure. Copyright 2008
John Wiley & Sons, Ltd.(-furyl)-1H-imidazole (1) has been prepared and characterized using infrared, Raman, and multidimensional
nuclear magnetic resonance spectroscopies. Two conformations of this species obtained by rotation of 1808,
approximately, around the CC inter-ring bond are detected. Likewise, the crystal and molecular structure of 1
has been analyzed by X-ray diffraction methods and it evidenced that both conformations are present in the lattice
with equal occupancy and linked in alternate way to the NH---N bonded polymeric chains along the crystal [101]
direction. Theoretical calculations have been carried out by employing the density functional theory (DFT)/B3LYP
method, in order to optimize the geometry in gas phase of both conformers and to support the assignments of the
vibrational bands of 1 to their normal modes. For a complete assignment of the compound, DFT calculations were
combined with Pulays SQMFF methodology in order to fit the theoretical frequency values to the experimental one.
The nuclear magnetic resonance spectrum observed for 1 is successfully compared with the calculated chemicals shifts
at B3LYP/6-311þþG** level of theory for the two conformers. Furthermore, natural bond orbital (NBO) analysis and
topological (AIM) calculations for an oligomer, containing three alternated units of the NH---N bonded chain found
in the crystal, reveals the characteristics of the hydrogen bonds present in the polymeric structure. Copyright 2008
John Wiley & Sons, Ltd.8,
approximately, around the CC inter-ring bond are detected. Likewise, the crystal and molecular structure of 1
has been analyzed by X-ray diffraction methods and it evidenced that both conformations are present in the lattice
with equal occupancy and linked in alternate way to the NH---N bonded polymeric chains along the crystal [101]
direction. Theoretical calculations have been carried out by employing the density functional theory (DFT)/B3LYP
method, in order to optimize the geometry in gas phase of both conformers and to support the assignments of the
vibrational bands of 1 to their normal modes. For a complete assignment of the compound, DFT calculations were
combined with Pulays SQMFF methodology in order to fit the theoretical frequency values to the experimental one.
The nuclear magnetic resonance spectrum observed for 1 is successfully compared with the calculated chemicals shifts
at B3LYP/6-311þþG** level of theory for the two conformers. Furthermore, natural bond orbital (NBO) analysis and
topological (AIM) calculations for an oligomer, containing three alternated units of the NH---N bonded chain found
in the crystal, reveals the characteristics of the hydrogen bonds present in the polymeric structure. Copyright 2008
John Wiley & Sons, Ltd.þþG** level of theory for the two conformers. Furthermore, natural bond orbital (NBO) analysis and
topological (AIM) calculations for an oligomer, containing three alternated units of the NH---N bonded chain found
in the crystal, reveals the characteristics of the hydrogen bonds present in the polymeric structure. Copyright 2008
John Wiley & Sons, Ltd. 2008
John Wiley & Sons, Ltd.
Supporting information may be found in the online version of this article.