Investigation of the aromaticity of mono, di, tri and tetraazaphenanthrene derivatives

References

[1] Rabjohn N. Organic syntheses, collective, vol. 4. Washington, D.C.: The National Academies Press, 1963.Search in Google Scholar

[2] Kalescky R, Kraka E, Cremer D. Description of Aromaticity with the help of vibrational spectroscopy: anthracene and phenanthrene. J Phys Chem A. 2014;118:223–37.10.1021/jp4092514Search in Google Scholar

[3] Cheucci G. Hydrodehalogenation of halogenated pyridines and quinolines by sodium borohydride/N,N,N0,N0–tetramethylethylenediamine under palladium catalysis. Tet Lett. 2010;51:1562–5.10.1016/j.tetlet.2010.01.053Search in Google Scholar

[4] Shestakov AN, Pankova AS, Kuznetsov MA. Cycloisomerization – a straightforward way to benzo[h]quinolines and benzo[c]acridines. Chem Heterocycl Compd. 2017;53:1103–13.10.1007/s10593-017-2179-5Search in Google Scholar

[5] Mamane V, Louerat F, Lehl J, Abboud MFY. A general and efficient method for the synthesis of benzo–(iso)quinoline derivatives. Tetrahedron. 2008;64:10699–705.10.1016/j.tet.2008.09.015Search in Google Scholar

[6] Ball CJ, Gilmore J, Willis MC. Copper–catalyzed tandem C_N bond formation: an efficient annulative synthesis of functionalized cinnolines. Angew Chem Int Ed. 2012;51:5718–22.10.1002/anie.201201529Search in Google Scholar

[7] Bencini A, Lippolis V. 1,10–Phenanthroline: A versatile building block for the construction of ligands for various purposes. Coord Chem Rev. 2010;254:2096–180.10.1016/j.ccr.2010.04.008Search in Google Scholar

[8] Summers LA. The phenanthrolines. Adv Heterocycl Chem. 1978;22:1–69.10.1016/S0065-2725(08)60102-6Search in Google Scholar

[9] Sammes PG, Yahioglu G. 1,10–phenanthroline: a versatile ligand. Chem Soc Rev. 1994;23:327–34.10.1039/cs9942300327Search in Google Scholar

[10] Luman CR, Castellano FN. Phenanthroline Ligands. In: McCleverty JA, Meyer TJ, Lever ABP, editors. Comprehensive coordination chemistry, vol. II. Oxford, UK: Elsevier, 2004:25.Search in Google Scholar

[11] Minkin VI, Glukhovtsev MN, Simkin BY. Aromaticity and antiaromaticity:electronic and structural aspects. New York: Wiley, 1994.Search in Google Scholar

[12] Schleyer PR, Jiao H. What is aromaticity? Pure Appl Chem. 1996;68:209–18.10.1351/pac199668020209Search in Google Scholar

[13] Glukhovtsev MN. Aromaticity today: energetic and structural criteria. J Chem Educ. 1997;74:132–6.10.1021/ed074p132Search in Google Scholar

[14] Krygowski TM, Cyranski MK, Czarnocki Z, Hafelinger G, Katritzky AR. Aromaticity: a theoretical concept of immense practical importance. Tetrahedron. 2000;56:1783–96.10.1016/S0040-4020(99)00979-5Search in Google Scholar

[15] Schleyer PR. Introduction: aromaticity. Chem Rev. 2001;101:1115–18.10.1021/cr0103221Search in Google Scholar

[16] Cyranski MK, Krygowski TM, Katritzky AR, Schleyer PR. To what extent can aromaticity be defi ned uniquely? J Org Chem. 2002;67:1333–8.10.1021/jo016255sSearch in Google Scholar

[17] Schleyer PR, Maerker C, Dransfeld A, Jiao H, Hommes NJRE. Nucleus independent chemical shifts: a simple and effi cient aromaticity probe. J Am Chem Soc. 1996;118:6317–18.10.1021/ja960582dSearch in Google Scholar

[18] Jiao H, Schleyer PR. Aromaticity of pericyclic reaction transition structures: magnetic evidence. J Phys Org Chem. 1998;11:655–62.10.1002/(SICI)1099-1395(199808/09)11:8/9<655::AID-POC66>3.0.CO;2-USearch in Google Scholar

[19] Schleyer PR, Kiran B, Simion DV, Sorensen TS. Does Cr(CO)₃ complexation reduce the aromaticity of benzene? J Amer Chem Soc. 2000;122:510–13.10.1021/ja9921423Search in Google Scholar

[20] Quinonero D, Garau C, Frontera A, Ballaster P, Costa A, Deya PM. Quantifi cation of aromaticity in oxocarbons: the problem of the fi ctitious ‘nonaromatic’ reference system. Chem Eur J. 2002;8:433–8.10.1002/1521-3765(20020118)8:2<433::AID-CHEM433>3.0.CO;2-TSearch in Google Scholar

[21] Patchkovskii S, Thiel W. Nucleus–independent chemical shifts from semiempirical calculations. J Mol Model. 2002;6:67–75.10.1007/PL00010736Search in Google Scholar

[22] Mohajeri A, Shahamirian M. Substituent effect on local aromaticity in mono and di–substituted heterocyclic analogs of naphthalene. J Phys Org Chem. 2010;23:440–50.10.1002/poc.1619Search in Google Scholar

[23] Krygowski TM, Palusiak M, Płonka A, Zachara–Horeglad JE. Relationship between substituent effect and aromaticity – Part III: naphthalene as a transmitting moiety for substituent effect. J Phys Org Chem. 2007;20:297–306.10.1002/poc.1127Search in Google Scholar

[24] Krygowski TM, Cyranski MK. Structural aspects of aromaticity. Chem Rev. 2001;101:1385−419.10.1021/cr990326uSearch in Google Scholar PubMed

[25] Gümüş S. The aromaticity of substituted diazanaphthalenes. Comput Theor Chem. 2011;963:263–7.10.1016/j.comptc.2010.10.026Search in Google Scholar

[26] Stewart JJP. Optimization of parameters for semi empirical methods I. Method J Comput Chem. 1989;10:209–20.10.1002/jcc.540100208Search in Google Scholar

[27] Stewart JJP. Optimization of parameters for semi empirical methods II. Applications J Comput Chem. 1989;10:221–64.10.1002/jcc.540100209Search in Google Scholar

[28] Leach AR. Molecular modelling. Essex: Longman, 1997.Search in Google Scholar

[29] Kohn W, Sham LJ. Self–consistent equations including exchange and correlation effects. Phys Rev. 1965;140:1133–8.10.1103/PhysRev.140.A1133Search in Google Scholar

[30] Parr RG, Yang W. Density functional theory of atoms and molecules. London: Oxford University Press, 1989.Search in Google Scholar

[31] Becke AD. Density–functional exchange–energy approximation with correct asymptotic behavior. Phys Rev A. 1988;38:3098–100.10.1103/PhysRevA.38.3098Search in Google Scholar

[32] Vosko SH, Vilk L, Nusair M. Accurate spin–dependent electron liquid correlation energies for local spin density calculations: a critical analysis. Can J Phys. 1980;58:1200–11.10.1139/p80-159Search in Google Scholar

[33] Lee C, Yang W, Parr RG. Development of the Colle–Salvetti correlation–energy formula into a functional of the electron density. Phys Rev B. 1988;37:785–9.10.1103/PhysRevB.37.785Search in Google Scholar

[34] Scuseria GE. Comparison of coupled–cluster results with a hybrid of Hartree–Fock and density functional theory. J Chem Phys. 1992;97:7528–30.10.1063/1.463977Search in Google Scholar

[35] Sosa C, Lee C. Density functional description of transition structures using nonlocal corrections. silylene insertion reactions into the hydrogen molecule. J Chem Phys. 1993;98:8004–11.10.1063/1.464554Search in Google Scholar

[36] Wilson PJ, Amos RD, Handy NC. Density functional predictions for metal and ligand nuclear shielding constants in diamagnetic closed–shell first–row transition–metal complexes. Phys Chem Chem Phys. 2000;2:187–94.10.1039/a907167iSearch in Google Scholar

[37] Pulay P, Hinton JF, Wolinski K. Nuclear magnetic shieldings and molecular structure. In: Tossel JA, editor. NATO ASI series C, vol. 386. Netherlands: Kluwer, 1993.Search in Google Scholar

[38] Hehre WJ, Radom L, Schleyer PR, Pople JA. Ab initio molecular orbital theory. New York: Wiley, 1986.Search in Google Scholar

[39] Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, et al. Wallingford, CT: Gaussian Inc., 2009.Search in Google Scholar

[40] Yu L, Zhou X, Wu D, Xiang H. Synthesis of phenazines by Cu–catalyzed homocoupling of 2–halogen anilines in water. J Organometall Chem. 2012;705:75–8.10.1016/j.jorganchem.2011.12.030Search in Google Scholar

[41] Stanger A. What is … aromaticity: a critique of the concept of aromaticity—can it really be defined? Chem Commun. 2009;15:1939–47.10.1039/b816811cSearch in Google Scholar PubMed