FT-IR, FT-Raman, UV-Visible, and NMR spectroscopy and vibrational properties of the labdane-type diterpene 13-epi-sclareol

Fernando E. Chain, Patricio Leyton, Carolina Paipa, Mario Fortuna, Silvia A. Brandán

Resultado de la investigación: Article

14 Citas (Scopus)

Resumen

(Chemical Equation Presented) In this work, FT-IR, FT-Raman, UV-Visible and NMR spectroscopies and density functional theory (DFT) calculations were employed to study the structural and vibrational properties of the labdane-type diterpene 13-epi-sclareol using the hybrid B3LYP method together with the 6-31G∗ basis set. Three stable structures with minimum energy found on the potential energy curves (PES) were optimized, and the corresponding molecular electrostatic potentials, atomic charges, bond orders, stabilization energies and topological properties were computed at the same approximation level. The complete assignment of the bands observed in the vibrational spectrum of 13-epi-sclareol was performed taking into account the internal symmetry coordinates for the three structures using the scaled quantum mechanical force field (SQMFF) methodology at the same level of theory. In addition, the force constants were calculated and compared with those reported in the literature for similar compounds. The predicted vibrational spectrum and the calculated 1HNMR and 13CNMR chemical shifts are in good agreement with the corresponding experimental results. Thetheoretical UV-Visspectra for themoststable structure of 13-epi-sclareol demonstrate a better correlation with the corresponding experimental spectrum. The study of the three conformers by means of the theory of atoms in molecules (AIM) revealed different H bond interactions and a strong dependence of the interactions on the distance between the involved atoms. Furthermore, the natural bond orbital (NBO) calculations showed the characteristics of the electronic delocalization for the two six-membered rings with chair conformations.

Idioma originalEnglish
Páginas (desde-hasta)303-313
Número de páginas11
PublicaciónSpectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Volumen138
DOI
EstadoPublished - 5 mar 2015
Publicado de forma externa

Huella dactilar

Diterpenes
Vibrational spectra
vibrational spectra
Nuclear magnetic resonance spectroscopy
Magnetic Resonance Spectroscopy
Orbital calculations
Atoms
nuclear magnetic resonance
Chemical shift
Potential energy
spectroscopy
field theory (physics)
seats
Density functional theory
chemical equilibrium
atoms
Conformations
Electrostatics
Stabilization
stabilization

ASJC Scopus subject areas

  • Instrumentation
  • Atomic and Molecular Physics, and Optics
  • Analytical Chemistry
  • Spectroscopy
  • Medicine(all)

Citar esto

Chain, Fernando E. ; Leyton, Patricio ; Paipa, Carolina ; Fortuna, Mario ; Brandán, Silvia A. / FT-IR, FT-Raman, UV-Visible, and NMR spectroscopy and vibrational properties of the labdane-type diterpene 13-epi-sclareol. En: Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy. 2015 ; Vol. 138. pp. 303-313.
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title = "FT-IR, FT-Raman, UV-Visible, and NMR spectroscopy and vibrational properties of the labdane-type diterpene 13-epi-sclareol",
abstract = "(Chemical Equation Presented) In this work, FT-IR, FT-Raman, UV-Visible and NMR spectroscopies and density functional theory (DFT) calculations were employed to study the structural and vibrational properties of the labdane-type diterpene 13-epi-sclareol using the hybrid B3LYP method together with the 6-31G∗ basis set. Three stable structures with minimum energy found on the potential energy curves (PES) were optimized, and the corresponding molecular electrostatic potentials, atomic charges, bond orders, stabilization energies and topological properties were computed at the same approximation level. The complete assignment of the bands observed in the vibrational spectrum of 13-epi-sclareol was performed taking into account the internal symmetry coordinates for the three structures using the scaled quantum mechanical force field (SQMFF) methodology at the same level of theory. In addition, the force constants were calculated and compared with those reported in the literature for similar compounds. The predicted vibrational spectrum and the calculated 1HNMR and 13CNMR chemical shifts are in good agreement with the corresponding experimental results. Thetheoretical UV-Visspectra for themoststable structure of 13-epi-sclareol demonstrate a better correlation with the corresponding experimental spectrum. The study of the three conformers by means of the theory of atoms in molecules (AIM) revealed different H bond interactions and a strong dependence of the interactions on the distance between the involved atoms. Furthermore, the natural bond orbital (NBO) calculations showed the characteristics of the electronic delocalization for the two six-membered rings with chair conformations.",
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FT-IR, FT-Raman, UV-Visible, and NMR spectroscopy and vibrational properties of the labdane-type diterpene 13-epi-sclareol. / Chain, Fernando E.; Leyton, Patricio; Paipa, Carolina; Fortuna, Mario; Brandán, Silvia A.

En: Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, Vol. 138, 05.03.2015, p. 303-313.

Resultado de la investigación: Article

TY - JOUR

T1 - FT-IR, FT-Raman, UV-Visible, and NMR spectroscopy and vibrational properties of the labdane-type diterpene 13-epi-sclareol

AU - Chain, Fernando E.

AU - Leyton, Patricio

AU - Paipa, Carolina

AU - Fortuna, Mario

AU - Brandán, Silvia A.

PY - 2015/3/5

Y1 - 2015/3/5

N2 - (Chemical Equation Presented) In this work, FT-IR, FT-Raman, UV-Visible and NMR spectroscopies and density functional theory (DFT) calculations were employed to study the structural and vibrational properties of the labdane-type diterpene 13-epi-sclareol using the hybrid B3LYP method together with the 6-31G∗ basis set. Three stable structures with minimum energy found on the potential energy curves (PES) were optimized, and the corresponding molecular electrostatic potentials, atomic charges, bond orders, stabilization energies and topological properties were computed at the same approximation level. The complete assignment of the bands observed in the vibrational spectrum of 13-epi-sclareol was performed taking into account the internal symmetry coordinates for the three structures using the scaled quantum mechanical force field (SQMFF) methodology at the same level of theory. In addition, the force constants were calculated and compared with those reported in the literature for similar compounds. The predicted vibrational spectrum and the calculated 1HNMR and 13CNMR chemical shifts are in good agreement with the corresponding experimental results. Thetheoretical UV-Visspectra for themoststable structure of 13-epi-sclareol demonstrate a better correlation with the corresponding experimental spectrum. The study of the three conformers by means of the theory of atoms in molecules (AIM) revealed different H bond interactions and a strong dependence of the interactions on the distance between the involved atoms. Furthermore, the natural bond orbital (NBO) calculations showed the characteristics of the electronic delocalization for the two six-membered rings with chair conformations.

AB - (Chemical Equation Presented) In this work, FT-IR, FT-Raman, UV-Visible and NMR spectroscopies and density functional theory (DFT) calculations were employed to study the structural and vibrational properties of the labdane-type diterpene 13-epi-sclareol using the hybrid B3LYP method together with the 6-31G∗ basis set. Three stable structures with minimum energy found on the potential energy curves (PES) were optimized, and the corresponding molecular electrostatic potentials, atomic charges, bond orders, stabilization energies and topological properties were computed at the same approximation level. The complete assignment of the bands observed in the vibrational spectrum of 13-epi-sclareol was performed taking into account the internal symmetry coordinates for the three structures using the scaled quantum mechanical force field (SQMFF) methodology at the same level of theory. In addition, the force constants were calculated and compared with those reported in the literature for similar compounds. The predicted vibrational spectrum and the calculated 1HNMR and 13CNMR chemical shifts are in good agreement with the corresponding experimental results. Thetheoretical UV-Visspectra for themoststable structure of 13-epi-sclareol demonstrate a better correlation with the corresponding experimental spectrum. The study of the three conformers by means of the theory of atoms in molecules (AIM) revealed different H bond interactions and a strong dependence of the interactions on the distance between the involved atoms. Furthermore, the natural bond orbital (NBO) calculations showed the characteristics of the electronic delocalization for the two six-membered rings with chair conformations.

KW - 13-epi-sclareol

KW - DFT calculations

KW - Force field

KW - Molecular structure

KW - Vibrational spectra

UR - http://www.scopus.com/inward/record.url?scp=84920774273&partnerID=8YFLogxK

U2 - 10.1016/j.saa.2014.11.049

DO - 10.1016/j.saa.2014.11.049

M3 - Article

C2 - 25498827

AN - SCOPUS:84920774273

VL - 138

SP - 303

EP - 313

JO - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

JF - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

SN - 1386-1425

ER -