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Theoretical study on the reaction of hydrogen atoms with aniline

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Abstract

The reaction of aniline with hydrogen atom is investigated herein using the hybrid meta-DFT functional of BB1 K. Hydrogen atom is found to preferentially add at an ortho position. However, the fate of the o-(C6H5NH2)H adduct is found to be solely the deactivation of the initial addition channel. The rate constant for the abstraction channel (C6H5NH2 + H → C6H5NH + H2) is fitted by the expression 1.10 × 10−11 exp(−4,200/T) cm3 molecule−1 s−1. Our calculated rate constant for the abstraction channel agrees very well with the available experimental measurements. Satisfactory agreement is found between calculated and experimental measurements for the displacement channel (C6H5NH2 + H → C6H6 + NH2). Our detailed analysis for the corresponding displacements in toluene and phenol suggests that the three systems exhibit similar behavior with regard to the relative importance of abstraction and displacement channels.

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Acknowledgments

This study has been supported by a grant of computing time from the Australian Centre of Advanced Computing and Communications (ac3).

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Authors and Affiliations

  1. Department of Chemical Engineering, Al-Hussein Bin Talal University, Ma’an, Jordan

    Marwan Batiha, Mohammednoor Altarawneh, Abdullah Alsofi, Ibrahem Altarawneh & Saleh Alrawadieh

  2. Department of Mining Engineering, Al-Hussein Bin Talal University, Ma’an, Jordan

    Mohammad Al-Harahsheh

Authors
  1. Marwan Batiha
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  2. Mohammednoor Altarawneh
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  3. Abdullah Alsofi
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  4. Mohammad Al-Harahsheh
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  5. Ibrahem Altarawneh
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  6. Saleh Alrawadieh
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Corresponding author

Correspondence to Mohammednoor Altarawneh.

Electronic supplementary material

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214_2011_940_MOESM1_ESM.doc

Supporting Information Available: Calculated total energies, zero-point energies, Cartesian coordinates, moments of inertia, and vibrational frequencies of all structures. (DOC 67 kb)

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Batiha, M., Altarawneh, M., Alsofi, A. et al. Theoretical study on the reaction of hydrogen atoms with aniline. Theor Chem Acc 129, 823–832 (2011). https://doi.org/10.1007/s00214-011-0940-x

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