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

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• 作者：Hadiseh Heydari ; Heidar Raissi ; Fariba Mollania
• 关键词：2 ; Nitrophenyl hydrosulfide ; Density functional theory (DFT) ; TD ; DFT ; AIM ; NBO ; Resonance parameters
• 刊名：Structural Chemistry
• 出版年：2015
• 出版时间：August 2015
• 年：2015
• 卷：26
• 期：4
• 页码：971-987
• 全文大小：915 KB
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• 作者单位：Hadiseh Heydari (1)
  Heidar Raissi (2)
  Fariba Mollania (2)
  
  1. Chemistry Department, Payame Noor University, Ardakan, Iran
  2. Chemistry Department, Birjand University, Birjand, Iran
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Computer Applications in Chemistry
  Physical Chemistry
  Theoretical and Computational Chemistry
  
• 出版者：Springer Netherlands
• ISSN：1572-9001

文摘

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, C2H5, CH3, CF3, NHCOCH3, NO2, OH, OCH3, SH, CH2F, CH2Cl, CH2Br, CH2OH, SH, SCH3, SCF3, SCOCH3, CH2CF3, CH2OCH3, CHO, COCH3, and OCHF2. The IMHB interaction has been explored by calculation of electron density ρ(r) and Laplacian ?sup>2 ρ(r) at the bond critical point using atoms-in-molecule (AIM) theory. The electron density (ρ) and Laplacian (?sup>2 ρ) properties, estimated by AIM calculations, indicate that H6···O1 bond possesses low ρ and positive ?sup>2 ρ values which are in agreement with electrostatic character of the HBs, whereas S5–H6 bond has covalent character (?sup>2 ρ?<?0). The natural bond orbital analysis is applied to get a more precise insight into the nature of such H6···O1 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.