Related Experiment Video
Updated: Jul 26, 2026

Analysis of Volatile and Oxidation Sensitive Compounds Using a Cold Inlet System and Electron Impact Mass Spectrometry
Published on: September 5, 2014
Electronic substituent effects in the electron impact mass spectrometry of 2-(arylazo)-4-phenylphenols
Guadalupe Pérez-Caballero1, Federico Jiménez-Cruz, Pablo Hernández Matamoros
1Facultad de Estudios Superiores Cuautitlán, Campo 1, Universidad Nacional Autónoma de México, Av. 1ro de Mayo s/n, Col. Santa María de las Torres, Cuautitlán Izcalli, Estado de México CP 54740. perezcg@servidor.unam.mx
Abstract:
A mass spectrometric study of a set of six novel 2-(arylazo)-4-phenylphenols 1-6 was performed. The electron impact spectra were acquired and analyzed for five of the compounds in order to establish a fragmentation pattern. The suggested pathways were investigated and confirmed by means of tandem mass spectrometry (MS/MS) experiments together with high-resolution accurate mass data. However, the sixth molecule, a sodium sulfonate salt, was studied using fast atom bombardment (FAB) ionization in positive and negative modes. In addition, some electronic substituent effects were investigated by analyzing Hammett-McLafferty linear free energy correlations for some peaks derived from the corresponding molecular ions. Also, the role of the O-H...N hydrogen bond present in the target compounds was analyzed. The roles of these H-bonds were consistent with the corresponding acidity constant values obtained experimentally as well as by theoretical quantum chemistry calculations using HF/6-31 + G(d,p) and B3LYP/6-31G(d,p). Some spectrometric data were correlated with topological properties derived from the atoms-in-molecules (AIM) theory.
More Related Videos
06:56Characterization of Synthetic Polymers via Matrix Assisted Laser Desorption Ionization Time of Flight (MALDI-TOF) Mass Spectrometry
Published on: June 10, 2018
11:45Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Related Concept Videos
Electrophilic Aromatic Substitution: Overview
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between the...
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
NMR Spectroscopy of Benzene Derivatives
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds
Mass Spectrometry: Aromatic Compound Fragmentation