NDLI: Quantum chemical study on influence of the substitution effect on the structural and electronic properties and intramolecular hydrogen bonding of 2-nitrophenyl hydrosulfide in ground and electronic excited state

Content Provider	Springer Nature Link
Author	Heydari, Hadiseh Raissi, Heidar Mollania, Fariba
Copyright Year	2014
Abstract	A density functional theory (DFT)-based quantum chemical computational study has been carried out to characterize the intramolecular hydrogen bonding (IMHB) interaction in 2-nitrophenyl hydrosulfide. This compound and its 24 derivatives are optimized by B3LYP method using 6-311++G** basis set in the gas phase and the water solution. The following substituents have been taken into consideration: F, Cl, Br, C$_{2}$H$_{5}$, CH$_{3}$, CF$_{3}$, NHCOCH$_{3}$, NO$_{2}$, OH, OCH$_{3}$, SH, CH$_{2}$F, CH$_{2}$Cl, CH$_{2}$Br, CH$_{2}$OH, SH, SCH$_{3}$, SCF$_{3}$, SCOCH$_{3}$, CH$_{2}$CF$_{3}$, CH$_{2}$OCH$_{3}$, CHO, COCH$_{3}$, and OCHF$_{2}$. The IMHB interaction has been explored by calculation of electron density ρ(r) and Laplacian ∇$^{2}$ ρ(r) at the bond critical point using atoms-in-molecule (AIM) theory. The electron density (ρ) and Laplacian (∇$^{2}$ ρ) properties, estimated by AIM calculations, indicate that H$_{6}$···O$_{1}$ bond possesses low ρ and positive ∇$^{2}$ ρ values which are in agreement with electrostatic character of the HBs, whereas S$_{5}$–H$_{6}$ bond has covalent character (∇$^{2}$ ρ < 0). The natural bond orbital analysis is applied to get a more precise insight into the nature of such H$_{6}$···O$_{1}$ interactions. Vibrational frequencies, several well-established indices of aromaticity, and physical properties such as dipole moment, chemical potential, and chemical hardness of these compounds have been systematically explored. Also, the excited-state properties of intramolecular hydrogen bonding in these systems have been investigated theoretically using the time-dependent DFT method.
Starting Page	971
Ending Page	987
Page Count	17
File Format	PDF
ISSN	10400400
Journal	Structural Chemistry
Volume Number	26
Issue Number	4
e-ISSN	15729001
Language	English
Publisher	Springer US
Publisher Date	2015-01-07
Publisher Place	New York
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	2-Nitrophenyl hydrosulfide Density functional theory (DFT) TD-DFT AIM NBO Resonance parameters Computer Applications in Chemistry Physical Chemistry Theoretical and Computational Chemistry
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry Condensed Matter Physics

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