Density Functional Theory Study of Intramolecular Hydrogen Bonding and Proton Transfer ino-Hydroxyaryl Ketimines

2008 ◽  
Vol 112 (15) ◽  
pp. 3478-3485 ◽  
Author(s):  
Aleksander Filarowski ◽  
Aleksander Koll ◽  
Poul Erik Hansen ◽  
Malgorzata Kluba
Keyword(s):  
Density Functional Theory ◽  
Hydrogen Bonding ◽  
Proton Transfer ◽  
Density Functional ◽  
Intramolecular Hydrogen Bonding ◽  
Density Functional Theory Study ◽  
Functional Theory ◽  
Intramolecular Hydrogen

CONFORMATIONAL PROPERTIES AND INTRAMOLECULAR HYDROGEN BONDING OF 3-AMINO-PROPENESELENAL: AN AB INITIO AND DENSITY FUNCTIONAL THEORY STUDIES

2013 ◽  
Vol 12 (04) ◽  
pp. 1350025 ◽  
Author(s):  
HEIDAR RAISSI ◽  
FARZANEH FARZAD ◽  
SHAHIRA ESLAMDOOST ◽  
FARIBA MOLLANIA
Keyword(s):  
Density Functional Theory ◽  
Hydrogen Bonding ◽  
Molecular Orbital ◽  
Continuum Model ◽  
Density Functional ◽  
Intramolecular Hydrogen Bonding ◽  
Stationary Points ◽  
Functional Theory ◽  
Polarized Continuum Model ◽  
Intramolecular Hydrogen

In the present work a conformational analysis of 3-amino-propeneselenal (APS) was performed using several computational methods, including DFT (B3LYP), MP2 and G2MP2. Harmonic vibrational frequencies were estimated at the same levels to confirm the nature of the stationary points found and also to account for the zero point vibrational energy (ZPVE) correction. Two intramolecular hydrogen bonds (HBs) established between the polar groups were identified by the structural geometric parameters. The excited-state properties of intramolecular hydrogen bonding in hydrogen bonded systems have been investigated theoretically using the time dependent density functional theory (TDDFT) method. The influence of the solvent on the stability order of conformers and the strength of intramolecular hydrogen bonding was considered using the polarized continuum model (PCM), the self-consistent isodensity polarized continuum model (SCI-PCM) and the integral equation formalism-polarizable continuum model (IEF-PCM) methods. The "atoms in molecules" theory of Bader was used to analyze critical points and to study the nature of HB in these systems. Natural bond orbital (NBO) analysis was also performed for better understanding the nature of intramolecular interactions. The calculated the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energies show that charge transfer occur within the molecule. Further verification of the obtained transition state structures were implemented via intrinsic reaction coordinate (IRC) analysis. Calculations of the 1 H NMR chemical shift at GIAO/B3LYP/6–311++G** level of theory are also presented.

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