TY - JOUR

T1 - Theoretical structural and vibrational properties of the artificial sweetener sucralose

AU - Brizuela, Alicia Beatriz

AU - Raschi, Ana Beatriz

AU - Castillo, María Victoria

AU - LEYTON BONGIORNO, PATRICIO ALEJANDRO

AU - Romano, Elida

AU - Brandán, Silvia Antonia

PY - 2013/3/15

Y1 - 2013/3/15

N2 - The structural and vibrational properties of sucralose were predicted by combining the available experimental infrared spectrum in the solid phase and ab initio calculations based on density functional theory (DFT). The highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) energy gaps HOMO-LUMO frontier orbitals, Natural Bond Orbital (NBO) and Atoms in Molecules (AIM) theory calculations were employed to study the stability, bond order, possible charge transfer and the topological properties of the glucopyran and glucofuran rings. To perform a complete assignment of the vibrational spectra, the density functional theory (DFT) calculations were combined with Pulay's Scaled Quantum Mechanics Force Field (SQMFF) methodology. The calculations were also used to predict the Raman spectrum of sucralose. A complete assignment of the 120 normal vibrational modes for sucralose was performed. Four strong bands in the infrared spectrum at 1093, 1040, 1025 and 990cm-1 are characteristic of sucralose in the solid phase. In this work, the calculated structural and vibrational properties of sucralose were analysed and compared with those of sucrose. The high stability of sucrose in relation to sucralose was justified by means of NBO and AIM analyses.

AB - The structural and vibrational properties of sucralose were predicted by combining the available experimental infrared spectrum in the solid phase and ab initio calculations based on density functional theory (DFT). The highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) energy gaps HOMO-LUMO frontier orbitals, Natural Bond Orbital (NBO) and Atoms in Molecules (AIM) theory calculations were employed to study the stability, bond order, possible charge transfer and the topological properties of the glucopyran and glucofuran rings. To perform a complete assignment of the vibrational spectra, the density functional theory (DFT) calculations were combined with Pulay's Scaled Quantum Mechanics Force Field (SQMFF) methodology. The calculations were also used to predict the Raman spectrum of sucralose. A complete assignment of the 120 normal vibrational modes for sucralose was performed. Four strong bands in the infrared spectrum at 1093, 1040, 1025 and 990cm-1 are characteristic of sucralose in the solid phase. In this work, the calculated structural and vibrational properties of sucralose were analysed and compared with those of sucrose. The high stability of sucrose in relation to sucralose was justified by means of NBO and AIM analyses.

KW - DFT calculations

KW - Force field

KW - Molecular structure

KW - Sucralose

KW - Vibrational spectra

UR - http://www.scopus.com/inward/record.url?scp=84872849858&partnerID=8YFLogxK

U2 - 10.1016/j.comptc.2012.12.017

DO - 10.1016/j.comptc.2012.12.017

M3 - Article

AN - SCOPUS:84872849858

VL - 1008

SP - 52

EP - 60

JO - Computational and Theoretical Chemistry

JF - Computational and Theoretical Chemistry

SN - 2210-271X

ER -