Quantum Mechanical Study on the Blue‐Shifting Hydrogen‐Bond between 3‐Aminophenol and <scp>CHX<sub>3</sub></scp> (X ═ F, Cl)

Lee, So Young; Kang, Hyuk

doi:10.1002/bkcs.10028

Bulletin Korean Chem Soc

2015

DOI: 10.1002/bkcs.10028

|View full text |Cite

Quantum Mechanical Study on the Blue‐Shifting Hydrogen‐Bond between 3‐Aminophenol and CHX₃ (X ═ F, Cl)

So Young Lee

Hyuk Kang

Abstract: Intermolecular bonding between 3-aminophenol and two halomethanes, namely fluoroform and chloroform, was quantum mechanically investigated. Several low-energy structures are found, and all geometries within 1 kcal/mol show π-hydrogen bonds between the aromatic ring and the hydrogen atom of the halomethane. The C H stretching frequency of halomethane involved in the π-hydrogen bond is blue-shifted, and the amount of blue shift is the largest with the most stable isomer and decreases with decreasing stability. B… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2015

2017

Publication Types

Select...

Article3

Relationship

Self Cite0

Independent3

Authors

Journals

Cited by 3 publications

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Quantum Mechanical Study on Hydrogen Bonds between 3‐Aminophenol and CH_xCl_4 − _x (x = 1, 2, 3): Effect of the Number of Halogen Atoms^#

Lee

Kang

2015

Bulletin Korean Chem Soc

View full text Add to dashboard Cite

Hydrogen bonds between 3‐aminophenol and three chlorine‐substituted methanes (CHCl3, CH2Cl2, and CH3Cl) were quantum mechanically studied at MP2/aug‐cc‐pVDZ level. Several low‐energy structures with a hydrogen bond were identified for all chlorinated methanes, and the properties of their CH stretching vibrations were investigated. When it is hydrogen‐bonded to 3‐aminophenol (3AP), the CH stretching frequency of CHCl3 is blue‐shifted by 18–54 cm−1, and its IR absorption intensity is 48–74 times increased, depending on the isomer. The symmetric and antisymmetric CH stretches of CH2Cl2 and CH3Cl are shifted in either direction by a few cm−1 upon hydrogen‐bonding to 3AP, and their IR intensity was increased by a few times. It is concluded that all chlorinated methanes can make a π‐hydrogen bond to 3AP but only CHCl3, the one with the most chlorine atoms, makes a blue‐shifting hydrogen bond, or an “antihydrogen bond”.

show abstract

Quantum Mechanical Study on Hydrogen Bonds between 3‐Aminophenol and CH_xCl_4 − _x (x = 1, 2, 3): Effect of the Number of Halogen Atoms^#

Lee

Kang

2015

Bulletin Korean Chem Soc

View full text Add to dashboard Cite

show abstract

A New Method for Preventing Corrosion Failure: Thiourea and Hexamethylenetetramine as Inhibitor for Copper

Wang

et al. 2016

Bulletin Korean Chem Soc

View full text Add to dashboard Cite

To investigate the inhibition mechanism of combined thiourea and hexamethylenetetramine as a corrosion inhibitor on the surface of copper in 0.5 M HCl solution, the electrochemical properties were measured by potentiodynamic polarization and electrochemical impedance spectroscopy measurements. The generated film was examined by scanning electron microscopy and X-ray photoelectron spectroscopy. Quantum chemical calculations and molecular dynamics simulations were performed to study the properties of thiourea and hexamethylenetetramine. The results suggest that the inhibitors can form strong bonds on the surface of copper. The combination of thiourea and hexamethylenetetramine resulted in stable films, which could inhibit the cathodic and anodic reactions and greatly reduce the diffusion of corrosive particles.

show abstract

The interaction strengths and spectroscopy parameters of the C2H2∙∙∙HX and HCN∙∙∙HX complexes (X = F, Cl, CN, and CCH) and related ternary systems valued by fluxes of charge densities: QTAIM, CCFO, and NBO calculations

et al. 2017

View full text Add to dashboard Cite

This theoretical work exhibits a new systematic study of structural parameters, electronic properties, infrared vibration modes, and molecular topography of hydrogen complexes, namely linear-type HCN⋯HX and T-type CH⋯HX (X = F, Cl, CN, and CCH). Ideally, the knowledge of the ternary systems of CH⋯HCN⋯HF and HCN⋯HCN⋯HF whose subparts integrate the linear and T-shaped complexes were used to give support in this current research. By means of computational calculations carried out in both levels B3LYP and MP2, the variations of the HX bond lengths are clearly overestimated in the HCN⋯HX linear complexes. In agreement with the analyses of the electrostatic potentials, the higher intermolecular energies of these complexes agree with the larger red-shifts in the stretch frequencies in HX. Also, the QTAIM descriptors and NBO calculations were used to inspect the interaction strength as well as to confirm the π cloud as a proton accepting center. By taking into account the absorption intensity ratio as a standard parameter to predict the interaction strength and intermolecular characterization, the formalism of the charge-charge flux-overlap modified (CCFO) was applied.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

hi@scite.ai

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Quantum Mechanical Study on the Blue‐Shifting Hydrogen‐Bond between 3‐Aminophenol and CHX₃ (X ═ F, Cl)

Cited by 3 publications

References 18 publications

Quantum Mechanical Study on Hydrogen Bonds between 3‐Aminophenol and CH_xCl_4 − _x (x = 1, 2, 3): Effect of the Number of Halogen Atoms^#

Quantum Mechanical Study on Hydrogen Bonds between 3‐Aminophenol and CH_xCl_4 − _x (x = 1, 2, 3): Effect of the Number of Halogen Atoms^#

A New Method for Preventing Corrosion Failure: Thiourea and Hexamethylenetetramine as Inhibitor for Copper

The interaction strengths and spectroscopy parameters of the C2H2∙∙∙HX and HCN∙∙∙HX complexes (X = F, Cl, CN, and CCH) and related ternary systems valued by fluxes of charge densities: QTAIM, CCFO, and NBO calculations

Contact Info

Product

Resources

About

Quantum Mechanical Study on the Blue‐Shifting Hydrogen‐Bond between 3‐Aminophenol and CHX3 (X ═ F, Cl)

Cited by 3 publications

References 18 publications

Quantum Mechanical Study on Hydrogen Bonds between 3‐Aminophenol and CHxCl4 − x (x = 1, 2, 3): Effect of the Number of Halogen Atoms#

Quantum Mechanical Study on Hydrogen Bonds between 3‐Aminophenol and CHxCl4 − x (x = 1, 2, 3): Effect of the Number of Halogen Atoms#

A New Method for Preventing Corrosion Failure: Thiourea and Hexamethylenetetramine as Inhibitor for Copper

The interaction strengths and spectroscopy parameters of the C2H2∙∙∙HX and HCN∙∙∙HX complexes (X = F, Cl, CN, and CCH) and related ternary systems valued by fluxes of charge densities: QTAIM, CCFO, and NBO calculations

Contact Info

Product

Resources

About

Quantum Mechanical Study on the Blue‐Shifting Hydrogen‐Bond between 3‐Aminophenol and CHX₃ (X ═ F, Cl)

Quantum Mechanical Study on Hydrogen Bonds between 3‐Aminophenol and CH_xCl_4 − _x (x = 1, 2, 3): Effect of the Number of Halogen Atoms^#

Quantum Mechanical Study on Hydrogen Bonds between 3‐Aminophenol and CH_xCl_4 − _x (x = 1, 2, 3): Effect of the Number of Halogen Atoms^#