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Theoretical Advances in Aromatic Nitration

Received: 16 February 2015     Accepted: 4 March 2015     Published: 14 March 2015
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Abstract

In this paper we want to present together our theoretical findings on aromatic nitration, involving both homocyclic and heterocyclic compounds. Our theoretical proposals have been introduced in recent years via several research communications. These theories convey new concepts in Organic Chemistry, such as Electric Hindrance, Autogenic Electromeric Effect, the formation of Precursor Complexes, as well as, short- and long-distance electric interactions in the reactive intermediates. These concepts explain the regiochemistry and the reaction yields, clearing up some obscurities found in Organic Chemistry. Thus, these theoretical considerations are filling gaps in the theory of supposedly well known chemical reactions, improving and updating the Chemical Education.

Published in Modern Chemistry (Volume 3, Issue 1)
DOI 10.11648/j.mc.20150301.12
Page(s) 9-13
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2015. Published by Science Publishing Group

Keywords

Electric Hindrance, Noncovalent Interactions, Precursor Complexes, Reaction Mechanisms, Reactive Intermediates

References
[1] W. M. Cumming, I. V. Hopper, and T. S. Wheeler, Systematic Organic Chemistry, 4th. ed., London: Constable, 1950, p. 280.
[2] K. Bahadur, and W. D. Patwardhan, “Preparation of o-nitroacetanilide”, Curr. Sci., vol. 37(17), p.492, 1968.
[3] F. Sánchez-Viesca, R. Gómez, and M. Berros, “Electric hindrance and precursor complexes in the regiochemistry of some nitrations”, J. Chem. Ed., vol. 88(7), pp. 944-946, 2011. DOI: dx.doi.org/10.1021/ed900030s
[4] M. Haouas, S. Bernasconi, A. Kogelbauer, and R. Prins, “An NMR study of the nitration of toluene over zeolites by nitric acid/acetic anhydride”, Phys. Chem. Chem. Phys., vol. 3, pp.5067-5075, 2001.
[5] Bond Polarization-Temporary Effects-Electromeric Effect (Online, access with the title). Tutors on Net, 2013.
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[8] F. Sánchez-Viesca, and M. Berros, “Espectroscopía y teoría de la regioquímica en la nitración de las benzopiridinas”, TIP Rev. Esp. Cienc. Quim. Biol., vol. 9(1), pp. 19-29, 2006; oai:unam.redalyc.org:43290103
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[10] E. Tchitchibabine, “Nitration de l’α-aminopyridine”, J. Soc. Phys. Chim. Russ., vol. 46(11), pp.1236-1244, 1914; in Bull. Soc. Chim. Fr., series 4, vol. 18, pp. 623-625, 1915.
[11] B. C. Uff, Pyridines and their benzo derivatives: reactivity of substituents, in A. R. Katritzky and C. W. Rees, eds., Comprehensive Heterocyclic Chemistry, Oxford: Pergamon, 1984, vol. 2, part 2A, p. 317.
[12] T. L. Gilchrist, Heterocyclic Chemistry, 3rd. ed., Essex: Longman, 1997, p. 166.
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[14] R. D. Brown, F. R. Burden, and W. Garland, “Microwave spectrum and dipole moment of pyridine N-oxide”, Chem. Phys. Lett., vol. 7(4), pp. 461-462, 1970.
[15] E. Ochiai, “A new classification of tertiary amine oxides”, Proc. Imp. Acad. Tokyo, vol. 19, pp. 307-311, 1943; Chem. Abstr., vol. 41, col. 5880d, 1947.
[16] E. Ochiai, E. Hayashi, and M. Katada, “Polarization of aromatic heterocyclic compounds. LVII. Nitration of pyridine 1-oxide”, Yakugaku Zasshi (J. Pharm. Soc. Japan), vol. 67, pp. 79-81, 1947; Chem. Abstr., vol. 45, col. 9538a, 1951.
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[18] H. J. den Hertog, and W. P. Combé, “Reactivity of 4-nitropyridine N-oxide: Preparation of 4-substituted derivatives of pyridine N-oxide and pyridine”, Rec. Trav. Chim., vol. 70(7), pp. 581-590, 1951.
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    Francisco Sánchez-Viesca, Reina Gómez, Martha Berros. (2015). Theoretical Advances in Aromatic Nitration. Modern Chemistry, 3(1), 9-13. https://doi.org/10.11648/j.mc.20150301.12

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    ACS Style

    Francisco Sánchez-Viesca; Reina Gómez; Martha Berros. Theoretical Advances in Aromatic Nitration. Mod. Chem. 2015, 3(1), 9-13. doi: 10.11648/j.mc.20150301.12

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    AMA Style

    Francisco Sánchez-Viesca, Reina Gómez, Martha Berros. Theoretical Advances in Aromatic Nitration. Mod Chem. 2015;3(1):9-13. doi: 10.11648/j.mc.20150301.12

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  • @article{10.11648/j.mc.20150301.12,
      author = {Francisco Sánchez-Viesca and Reina Gómez and Martha Berros},
      title = {Theoretical Advances in Aromatic Nitration},
      journal = {Modern Chemistry},
      volume = {3},
      number = {1},
      pages = {9-13},
      doi = {10.11648/j.mc.20150301.12},
      url = {https://doi.org/10.11648/j.mc.20150301.12},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.mc.20150301.12},
      abstract = {In this paper we want to present together our theoretical findings on aromatic nitration, involving both homocyclic and heterocyclic compounds. Our theoretical proposals have been introduced in recent years via several research communications. These theories convey new concepts in Organic Chemistry, such as Electric Hindrance, Autogenic Electromeric Effect, the formation of Precursor Complexes, as well as, short- and long-distance electric interactions in the reactive intermediates. These concepts explain the regiochemistry and the reaction yields, clearing up some obscurities found in Organic Chemistry. Thus, these theoretical considerations are filling gaps in the theory of supposedly well known chemical reactions, improving and updating the Chemical Education.},
     year = {2015}
    }
    

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  • TY  - JOUR
    T1  - Theoretical Advances in Aromatic Nitration
    AU  - Francisco Sánchez-Viesca
    AU  - Reina Gómez
    AU  - Martha Berros
    Y1  - 2015/03/14
    PY  - 2015
    N1  - https://doi.org/10.11648/j.mc.20150301.12
    DO  - 10.11648/j.mc.20150301.12
    T2  - Modern Chemistry
    JF  - Modern Chemistry
    JO  - Modern Chemistry
    SP  - 9
    EP  - 13
    PB  - Science Publishing Group
    SN  - 2329-180X
    UR  - https://doi.org/10.11648/j.mc.20150301.12
    AB  - In this paper we want to present together our theoretical findings on aromatic nitration, involving both homocyclic and heterocyclic compounds. Our theoretical proposals have been introduced in recent years via several research communications. These theories convey new concepts in Organic Chemistry, such as Electric Hindrance, Autogenic Electromeric Effect, the formation of Precursor Complexes, as well as, short- and long-distance electric interactions in the reactive intermediates. These concepts explain the regiochemistry and the reaction yields, clearing up some obscurities found in Organic Chemistry. Thus, these theoretical considerations are filling gaps in the theory of supposedly well known chemical reactions, improving and updating the Chemical Education.
    VL  - 3
    IS  - 1
    ER  - 

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Author Information
  • Organic Chemistry Department, Faculty of Chemistry, National Autonomous University of Mexico, México, DF, México

  • Organic Chemistry Department, Faculty of Chemistry, National Autonomous University of Mexico, México, DF, México

  • Organic Chemistry Department, Faculty of Chemistry, National Autonomous University of Mexico, México, DF, México

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