Uma Revisão Sistemática sobre Interações de Halogênio em Derivados de Nitrobenzeno Substituídos
Resumo
Este trabalho buscou analisar as interações de halogênio observadas em compostos derivados de 2,6-dibromonitrobenzeno, encontradas na literatura. As pesquisas foram realizadas nas bases de dados: Google Academic, Springer, PubMed e Science Direct. Foram identificados 102 trabalhos na busca inicial, dos quais somente 11 foram selecionados depois da aplicação dos critérios de inclusão e exclusão e da leitura dos trabalhos. Baseado nos trabalhos selecionados, somente parâmetros geométricos são considerados para investigação das interações de halogênio, cerca de 7 trabalhos. A partir desses dados, infere-se a demanda por uma análise mais detalhada do ponto de vista teórico das interações envolvendo átomos de halogênio para essa classe de compostos. Sobretudo, considerando as interações entre dois átomos da mesma família.
Referências
1. Cavallo G, Metrangolo P, Milani R, et al. The Halogen Bond. Chem Rev. 2016;116(4):2478-2601. doi:10.1021/acs.chemrev.5b00484.
2. Legon AC. The halogen bond: an interim perspective. Phys Chem Chem Phys. 2010;12(28):7736-7747. doi: 10.1039/C002129F.
3. Benesi HA, Hildebrand JH. ULTRAVIOLET ABSORPTION BANDS OF IODINE IN AROMATIC HYDROCARBONS. J Am Chem Soc. 1948;70(8):2832-2833. doi: 10.1021/ja01188a528.
4. Benesi HA, Hildebrand JH. A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons. J Am Chem Soc. 1949;71(8):2703-2707. doi: 10.1021/ja01176a030.
5. Mulliken RS. Structures of Complexes Formed by Halogen Molecules with Aromatic and with Oxygenated Solvents1. J Am Chem Soc. 1950;72(1):600-608. doi: 10.1021/ja01157a151.
6. O. Hassel; Knut O. Stromme. Crystal Structure of the Addition Compound 1,4-Dioxan-Chlorine. Acta Chem Scand - ACTA CHEM SCAND. 1959;13:1775-1780.
7. Odd Hassel. Strutural Aspects of Interatomic Charge-Transfer Bonding. Science (80- ). 1970;170(3957).
8. Dahl T, Hassel O, J. Ballhausen C, et al. Solid Adducts of Hexamethylenetetramine and Trihalogenomethanes. Crystal Structure of the 1:1 Iodoform Compound. Vol 24.; 1970. doi: 10.3891/acta.chem.scand.24-0377.
9. Clark T, Hennemann M, Murray J, Politzer P. Halogen Bonding: The σ-Hole. Vol 13.; 2007. doi: 10.1007/s008940060130-2.
10. Goud NR, Bolton O, Burgess EC, Matzger AJ. Unprecedented Size of the σ-Holes on 1,3,5-Triiodo-2,4,6 trinitrobenzene Begets Unprecedented Intermolecular Interactions. Cryst Growth Des. 2016;16(3):1765-1771. doi: 10.1021/acs.cgd.6b00074.
11. Spackman MA, Jayatilaka D. Hirshfeld surface analysis. CrystEngComm. 2009;11(1):19-32. doi: 10.1039/B818330A.
12. Syzgantseva OA, Tognetti V, Joubert L. On the Physical Nature of Halogen Bonds: A QTAIM Study. J Phys Chem A. 2013;117(36):8969-8980. doi: 10.1021/jp4059774.
13. Pounds AJ. Valency and Bonding: A Natural Bond Orbital Donor– Acceptor Perspective (Frank Weinhold and Clark Landis). J Chem Educ. 2007;84(1):43. doi: 10.1021/ed084p43.
14. Weinhold F. Natural bond orbital analysis: A critical overview of relationships to alternative bonding perspectives. J Comput Chem. 2012;33(30):2363-2379. doi: 10.1002/jcc.23060.
15. Foster JP, Weinhold F. Natural hybrid orbitals. J Am Chem Soc. 1980;102(24):7211-7218. doi: 10.1021/ja00544a007.
16. Kohn W, Sham LJ. Self-Consistent Equations Including Exchange and Correlation Effects. Phys Rev. 1965;140(4A):A1133-A1138. doi: 10.1103/PhysRev.140.A1133.
17. Gavezzotti A. Non-conventional bonding between organic molecules. The ‘halogen bond’ in crystalline systems. Mol Phys. 2008;106(12-13):1473-1485. doi: 10.1080/00268970802060674.
18. Groom CR, Bruno IJ, Lightfoot MP, Ward SC. The Cambridge Structural Database. Acta Crystallogr Sect B Struct Sci Cryst Eng Mater. 2016;72(2):171-179. doi: 10.1107/S2052520616003954.
19. Frisch MJ, Trucks GW, Schlegel HB. Gaussian 03, Revision B.04. Vol null. (null, ed.).; 2003.
20. Merz K. Substitution Effect on Crystal Packings of Iodobenzonitriles and Iodophenols. Cryst Growth Des. 2006;6(7):1615-1619. doi: 10.1021/cg060067j.
21. Mossakowska I, Wójcik GM. Supramolecular assemblies of singlesubstituted nitrobenzenes in their experimental and predicted crystal structures. J Mol Struct. 2010;967(1):119-130. doi: https://doi.org/10.1016/j.molstruc.2009.12.047.
22. Hoque MM, Halim MA, Rahman MM, Hossain MI, Khan MW. Synthesis and structural insights of substituted 2 iodoacetanilides and 2-iodoanilines. J Mol Struct. 2013;1054-1055:367-374. doi: https://doi.org/10.1016/j.molstruc.2013.10.011.
23. Romero JA, Aguirre Hernández G, Bernès S. Anomalous halogen bonds in the crystal structures of 1,2,3-tri bromo-5-nitro-benzene and 1,3-di-bromo-2-iodo-5-nitro-benzene. Acta Crystallogr Sect E, Crystallogr Commun. 2015;71(Pt 8):960-964. doi: 10.1107/ S2056989015013377.
24. Wang J-R, Fan X, Ding Q, Mei X. Determination of absolute configuration using heavy atom based co crystallization method: Halogen atom effects. J Mol Struct. 2016;1119:269-275. doi: https://doi.org/10.1016/j.molstruc.2016.04.084.
25. Navarrete Guitérrez A, Aguirre Hernández G, Bernès S. Crystal structures of p-substituted derivatives of 2,6-di methylbromo-benzene with ½ ≤ Z’ ≤ 4. Acta Crystallogr Sect E, Crystallogr Commun. 2016;72(Pt 12):1762-1767. doi: 10.1107/ S2056989016017485.
26. Santos LA, da Cunha EFF, Ramalho TC. Toward the Classical Description of Halogen Bonds: A Quantum Based Generalized Empirical Potential for Fluorine, Chlorine, and Bromine. J Phys Chem A. 2017;121(12):2442-2451. doi: 10.1021/acs.jpca.6b13112.
27. Bader RFW. Atoms in Molecules. Vol null. (null, ed.).; 1990.
28. Bader RFW. Atoms in molecules. Acc Chem Res. 1985;18(1):9-15. doi: 10.1021/ar00109a003.
29. Reed AE, Curtiss LA, Weinhold F. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem Rev. 1988;88(6):899-926. doi: 10.1021/cr00088a005.
