A New Model for Prediction of One Electron Reduction Potential of Nitroaryl Compounds |
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Authors: | Reza Fareghi‐Alamdari Farzad Zandi Mohammad Hossein Keshavarz |
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Institution: | 1. College of Chemistry and Chemical Engineering, Malek‐ashtar University of Technology, Tehran, 16765–3454, Iran;2. Department of Chemistry, Malek‐ashtar University of Technology, Shahin‐shahr P.O. Box 83145/115, Iran |
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Abstract: | This paper introduces a simple model for prediction of one electron reduction potential E(RNO2/R ? NO2–)] of various nitroaryl compounds. The new method uses energy difference between highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) in gas phase at the B3LYP/6‐311++G** level (ΔEHOMO‐LUMO) and some structural parameters. It was used for 35 nitroaryl compounds including nitrobenzenes, nitrofurans, 2‐nitroimidazoles, 4‐nitroimidazoles, 5‐ninuintidazoles, nitroazaindoles, nitroacridines, and miscellaneous nitroaryl compounds. The root mean square (rms) percent deviation and the average absolute error of predictions of E(RNO2/R ? NO2–) relative to experiment were decreased from 12.4 % and 0.42 V to 3.5 % and 0.11 V, respectively, upon consideration of several structural parameters. Increment of the value of ΔEHOMO‐LUMO and inclusion of specific polar groups can increase thermodynamic stability of these compounds. |
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Keywords: | One electron Reduction potential Nitroaryl compound HOMO LUMO Radicals |
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