메뉴 건너뛰기




Volumn 976, Issue 1-3, 2011, Pages 19-29

Pi-electron delocalization in aza derivatives of naphthalene and indole

Author keywords

Indole; Naphthalene; Natural charge; Position isomer; Stability

Indexed keywords


EID: 84555218468     PISSN: 2210271X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.comptc.2011.07.036     Document Type: Article
Times cited : (10)

References (64)
  • 4
    • 0006369138 scopus 로고
    • Aromaticity, Pseudoaromaticity and Antiaromaticity
    • (Eds.), Proc. of An International Symposium held in Jerusalem 1970, Israel Academy of Sciences and Humanities, Jerusalem.
    • E.D. Bergmann, B. Pullman (Eds.), Aromaticity, Pseudoaromaticity and Antiaromaticity, Proc. of An International Symposium held in Jerusalem 1970, Israel Academy of Sciences and Humanities, Jerusalem, 1971.
    • (1971)
    • Bergmann, E.D.1    Pullman, B.2
  • 5
    • 27744530363 scopus 로고    scopus 로고
    • Nucleus independent chemical shifts (NICS) as an aromaticity criterion
    • Chen Z., Wannere C.S., Corminboeuf C., Puchta R., Schleyer P.v.R. Nucleus independent chemical shifts (NICS) as an aromaticity criterion. Chem. Rev. 2005, 105:3842-3888.
    • (2005) Chem. Rev. , vol.105 , pp. 3842-3888
    • Chen, Z.1    Wannere, C.S.2    Corminboeuf, C.3    Puchta, R.4    Schleyer, P.5
  • 8
    • 0034669522 scopus 로고    scopus 로고
    • 2 (X=N, P, C-, Si-, O+, and S+): an ab initio and DFT study
    • 2 (X=N, P, C-, Si-, O+, and S+): an ab initio and DFT study. J. Am. Chem. Soc. 2000, 122:11173-11181.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 11173-11181
    • Priyakumar, U.D.1    Sastry, G.N.2
  • 9
    • 0037134939 scopus 로고    scopus 로고
    • Synthesis and properties of the first stable germa-benzene
    • Nakata N., Takeda N., Tokitoh N. Synthesis and properties of the first stable germa-benzene. J. Am. Chem. Soc. 2002, 124:6914-6920.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 6914-6920
    • Nakata, N.1    Takeda, N.2    Tokitoh, N.3
  • 10
    • 0000529494 scopus 로고    scopus 로고
    • Structures, vibrational frequencies and polarizabilities of diazaborinines, triazadiborinines, azaboroles, and oxazaboroles
    • Doerksen R.J., Thakkar A.J. Structures, vibrational frequencies and polarizabilities of diazaborinines, triazadiborinines, azaboroles, and oxazaboroles. J. Phys. Chem. A 1999, 103:2141-2151.
    • (1999) J. Phys. Chem. A , vol.103 , pp. 2141-2151
    • Doerksen, R.J.1    Thakkar, A.J.2
  • 11
    • 44649159599 scopus 로고    scopus 로고
    • Aromaticity in terms of ring critical point properties
    • Mohajeri A., Ashrafi A. Aromaticity in terms of ring critical point properties. Chem. Phys. Lett. 2008, 458:378-383.
    • (2008) Chem. Phys. Lett. , vol.458 , pp. 378-383
    • Mohajeri, A.1    Ashrafi, A.2
  • 12
    • 68049137946 scopus 로고    scopus 로고
    • Springer-Verlag, Berlin Heidelberg, T.M. Krygowski, M.K. Cyrański (Eds.)
    • Aromaticity in Heterocyclic Compounds 2009, Springer-Verlag, Berlin Heidelberg. T.M. Krygowski, M.K. Cyrański (Eds.).
    • (2009) Aromaticity in Heterocyclic Compounds
  • 13
    • 2942580883 scopus 로고    scopus 로고
    • Aromaticity as a cornerstone of hetero-cyclic chemistry
    • Balaban A.T., Oniciu D.C., Katritzky A.R. Aromaticity as a cornerstone of hetero-cyclic chemistry. Chem. Rev. 2004, 104:2777-2812.
    • (2004) Chem. Rev. , vol.104 , pp. 2777-2812
    • Balaban, A.T.1    Oniciu, D.C.2    Katritzky, A.R.3
  • 16
    • 0042621862 scopus 로고
    • Aromaticity as a quantitative concept. 1. A statistical demonstration of the orthogonality of classical and magnetic aromaticity in five- and six-membered heterocycles
    • Katritzky A.R., Barczyński P., Musumarra G., Pisano D., Szafran M. Aromaticity as a quantitative concept. 1. A statistical demonstration of the orthogonality of classical and magnetic aromaticity in five- and six-membered heterocycles. J. Am. Chem. Soc. 1989, 111:7-15.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 7-15
    • Katritzky, A.R.1    Barczyński, P.2    Musumarra, G.3    Pisano, D.4    Szafran, M.5
  • 17
    • 0001719845 scopus 로고
    • Aromaticity as a quantitative concept. 2. Sixteen familiar five- and six-membered monocyclic heterocycles
    • Katritzky A.R., Feygelman V., Musumarra G., Barczyński P., Szafran M. Aromaticity as a quantitative concept. 2. Sixteen familiar five- and six-membered monocyclic heterocycles. J. Prakt. Chem. 1990, 332:853-869.
    • (1990) J. Prakt. Chem. , vol.332 , pp. 853-869
    • Katritzky, A.R.1    Feygelman, V.2    Musumarra, G.3    Barczyński, P.4    Szafran, M.5
  • 18
    • 0000094989 scopus 로고
    • Aromaticity as a quantitative concept. 4. Less familiar five- and six-membered monocyclic heterocycles
    • Katritzky A.R., Barczyński P. Aromaticity as a quantitative concept. 4. Less familiar five- and six-membered monocyclic heterocycles. J. Prakt. Chem. 1990, 332:885-897.
    • (1990) J. Prakt. Chem. , vol.332 , pp. 885-897
    • Katritzky, A.R.1    Barczyński, P.2
  • 23
    • 26644431589 scopus 로고    scopus 로고
    • A computational study of the arsabenzenes: structure, properties and aromaticity
    • Ghiasi R. A computational study of the arsabenzenes: structure, properties and aromaticity. J. Org. Met. Chem. 2005, 690:4761-4767.
    • (2005) J. Org. Met. Chem. , vol.690 , pp. 4761-4767
    • Ghiasi, R.1
  • 24
    • 0030457576 scopus 로고    scopus 로고
    • Are the most stable fused heterobicycles the most aromatic?
    • Subramanian G., Schleyer P.v.R., Jiao H. Are the most stable fused heterobicycles the most aromatic?. Angew. Chem., Int. Ed. Engl. 1996, 35:2638-2641.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 2638-2641
    • Subramanian, G.1    Schleyer, P.2    Jiao, H.3
  • 25
    • 0000803696 scopus 로고    scopus 로고
    • Structure, stability and aromaticity of bis-heteropentalenes
    • Novak I. Structure, stability and aromaticity of bis-heteropentalenes. J. Mol. Struct. (THEOCHEM) 1997, 398:315-323.
    • (1997) J. Mol. Struct. (THEOCHEM) , vol.398 , pp. 315-323
    • Novak, I.1
  • 26
    • 0035887261 scopus 로고    scopus 로고
    • Aromaticity of dihetero analogues of pentalene dianion. X-ray and ab initio studies of eight methyl furo[3,2-b]pyrrole-5-carboxylate derivatives and five methyl furo[2,3-b]pyrrole-5-carboxylate derivatives
    • Cyrański M.K., Krygowski T.M., Krutošíková A., Sleziak R. Aromaticity of dihetero analogues of pentalene dianion. X-ray and ab initio studies of eight methyl furo[3,2-b]pyrrole-5-carboxylate derivatives and five methyl furo[2,3-b]pyrrole-5-carboxylate derivatives. Tetrahedron 2001, 57:8867-8873.
    • (2001) Tetrahedron , vol.57 , pp. 8867-8873
    • Cyrański, M.K.1    Krygowski, T.M.2    Krutošíková, A.3    Sleziak, R.4
  • 27
    • 0000929590 scopus 로고
    • Topological charge stabilization
    • Gimarc B.M. Topological charge stabilization. J. Am. Chem. Soc. 1983, 105:1979-1984.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 1979-1984
    • Gimarc, B.M.1
  • 28
    • 33750957758 scopus 로고    scopus 로고
    • Local aromaticity study of heterocycles using n-center delocalization indices: the role of aromaticity on the relative stability of position isomers
    • Mandado M., Otero N., Mosquera R.A. Local aromaticity study of heterocycles using n-center delocalization indices: the role of aromaticity on the relative stability of position isomers. Tetrahedron 2006, 62:12204-12210.
    • (2006) Tetrahedron , vol.62 , pp. 12204-12210
    • Mandado, M.1    Otero, N.2    Mosquera, R.A.3
  • 29
    • 0000867708 scopus 로고
    • Definition of aromaticity basing on the harmonic oscillator model
    • Kruszewski J., Krygowski T.M. Definition of aromaticity basing on the harmonic oscillator model. Tetrahedron Lett. 1972, 3839-3842.
    • (1972) Tetrahedron Lett. , pp. 3839-3842
    • Kruszewski, J.1    Krygowski, T.M.2
  • 30
    • 27544510655 scopus 로고
    • Crystallographic studies of inter- and intramolecular interactions reflected in aromatic character of pi-electron systems
    • Krygowski T.M. Crystallographic studies of inter- and intramolecular interactions reflected in aromatic character of pi-electron systems. J. Chem. Inf. Comput. Sci. 1993, 33:70-78.
    • (1993) J. Chem. Inf. Comput. Sci. , vol.33 , pp. 70-78
    • Krygowski, T.M.1
  • 31
    • 0342973214 scopus 로고    scopus 로고
    • Separation of the energetic and geometric contributions to the aromaticity of π-electron carbocyclics
    • Krygowski T.M., Cyrański M.K. Separation of the energetic and geometric contributions to the aromaticity of π-electron carbocyclics. Tetrahedron 1996, 52:1713-1722.
    • (1996) Tetrahedron , vol.52 , pp. 1713-1722
    • Krygowski, T.M.1    Cyrański, M.K.2
  • 33
    • 27744481399 scopus 로고    scopus 로고
    • Theoretical evaluation of electron delocalization in aromatic molecules by means of atoms in molecules (AIM) and electron localization function (ELF) topological approaches
    • Poater J., Duran M., Solà M., Silvi B. Theoretical evaluation of electron delocalization in aromatic molecules by means of atoms in molecules (AIM) and electron localization function (ELF) topological approaches. Chem. Rev. 2005, 105:3911-3947.
    • (2005) Chem. Rev. , vol.105 , pp. 3911-3947
    • Poater, J.1    Duran, M.2    Solà, M.3    Silvi, B.4
  • 34
    • 77953083924 scopus 로고    scopus 로고
    • Substituent effect on local aromaticity in mono and di-substituted heterocyclic analogs of naphthalene
    • Mohajeri A., Shahamirian M. Substituent effect on local aromaticity in mono and di-substituted heterocyclic analogs of naphthalene. J. Phys. Org. Chem. 2010, 23:440-450.
    • (2010) J. Phys. Org. Chem. , vol.23 , pp. 440-450
    • Mohajeri, A.1    Shahamirian, M.2
  • 35
    • 77954955865 scopus 로고    scopus 로고
    • The role of substituent on the aromaticity variation of mono- and di-substituted aza analogs of indole
    • Mohajeri A., Shahamirian M. The role of substituent on the aromaticity variation of mono- and di-substituted aza analogs of indole. J. Mol. Struct. (THEOCHEM) 2010, 951:72-76.
    • (2010) J. Mol. Struct. (THEOCHEM) , vol.951 , pp. 72-76
    • Mohajeri, A.1    Shahamirian, M.2
  • 36
    • 0001354699 scopus 로고
    • Absolute hardness as a measure of aromaticity
    • Zhou Z., Parr R.G., Garst J.F. Absolute hardness as a measure of aromaticity. Tetrahedron Lett. 1988, 29:4843-4846.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 4843-4846
    • Zhou, Z.1    Parr, R.G.2    Garst, J.F.3
  • 37
    • 0347136120 scopus 로고
    • New measures of aromaticity: absolute hardness and relative hardness
    • Zhou Z., Parr R.G. New measures of aromaticity: absolute hardness and relative hardness. J. Am. Chem. Soc. 1989, 111:7371-7379.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 7371-7379
    • Zhou, Z.1    Parr, R.G.2
  • 38
    • 0000460332 scopus 로고
    • Measuring aromaticity
    • Zhou Z. Measuring aromaticity. Int. Rev. Phys. Chem. 1992, 11:243-261.
    • (1992) Int. Rev. Phys. Chem. , vol.11 , pp. 243-261
    • Zhou, Z.1
  • 39
    • 0942279545 scopus 로고    scopus 로고
    • Relative hardness as a measure of aromaticity
    • De Proft F., Geerlings P. Relative hardness as a measure of aromaticity. Phys. Chem. Chem. Phys. 2004, 6:242-248.
    • (2004) Phys. Chem. Chem. Phys. , vol.6 , pp. 242-248
    • De Proft, F.1    Geerlings, P.2
  • 40
    • 0001627107 scopus 로고
    • Molecular Zeeman effect of cyclopentadiene and isoprene and comparison of the magnetic susceptibility anisotropies
    • Flygare W.H., Benson R.C. Molecular Zeeman effect of cyclopentadiene and isoprene and comparison of the magnetic susceptibility anisotropies. J. Am. Chem. Soc. 1970, 92:7523-7529.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 7523-7529
    • Flygare, W.H.1    Benson, R.C.2
  • 41
    • 33749838646 scopus 로고
    • Magnetic interactions in molecules and an analysis of molecular electronic charge distribution from magnetic parameters
    • Flygare W.H. Magnetic interactions in molecules and an analysis of molecular electronic charge distribution from magnetic parameters. Chem. Rev. 1974, 74:653-687.
    • (1974) Chem. Rev. , vol.74 , pp. 653-687
    • Flygare, W.H.1
  • 42
    • 0000586431 scopus 로고
    • The molecular Zeeman effect in diamagnetic molecules and the determination of molecular magnetic moments (g values), magnetic susceptibilities, and molecular quadrupole moments
    • Flygare W.H., Benson R.C. The molecular Zeeman effect in diamagnetic molecules and the determination of molecular magnetic moments (g values), magnetic susceptibilities, and molecular quadrupole moments. Mol. Phys. 1971, 20:225-250.
    • (1971) Mol. Phys. , vol.20 , pp. 225-250
    • Flygare, W.H.1    Benson, R.C.2
  • 43
    • 0031930407 scopus 로고    scopus 로고
    • Global and local aromaticity in porphyrins: an analysis based on molecular geometries and nucleus independent chemical shifts
    • Cyrański M.K., Krygowski T.M., Wisiorowski M., van Eikema Hommes N.J.R., Schleyer P.v.R. Global and local aromaticity in porphyrins: an analysis based on molecular geometries and nucleus independent chemical shifts. Angew. Chem. Int. Ed. 1998, 37:177-180.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 177-180
    • Cyrański, M.K.1    Krygowski, T.M.2    Wisiorowski, M.3    van Eikema Hommes, N.J.R.4    Schleyer, P.5
  • 44
    • 0000630951 scopus 로고    scopus 로고
    • Introduction: aromaticity
    • Schleyer P.v.R. Introduction: aromaticity. Chem. Rev. 2001, 101:1115-1118.
    • (2001) Chem. Rev. , vol.101 , pp. 1115-1118
    • Schleyer, P.1
  • 45
    • 0035353541 scopus 로고    scopus 로고
    • Structural aspects of aromaticity
    • Krygowski T.M., Cyrański M.K. Structural aspects of aromaticity. Chem. Rev. 2001, 101:1385-1420.
    • (2001) Chem. Rev. , vol.101 , pp. 1385-1420
    • Krygowski, T.M.1    Cyrański, M.K.2
  • 46
    • 0030598025 scopus 로고    scopus 로고
    • Separation of the energetic and geometric contributions to the aromaticity. Part IV. A general model for the π-electron systems
    • Krygowski T.M., Cyrański M.K. Separation of the energetic and geometric contributions to the aromaticity. Part IV. A general model for the π-electron systems. Tetrahedron 1996, 52:10255-10264.
    • (1996) Tetrahedron , vol.52 , pp. 10255-10264
    • Krygowski, T.M.1    Cyrański, M.K.2
  • 47
    • 32144434172 scopus 로고    scopus 로고
    • Nucleus independent chemical shifts (NICS): distance dependence and revised criteria for aromaticity and antiaromaticity
    • Stanger A. Nucleus independent chemical shifts (NICS): distance dependence and revised criteria for aromaticity and antiaromaticity. J. Org. Chem. 2006, 71:883-893.
    • (2006) J. Org. Chem. , vol.71 , pp. 883-893
    • Stanger, A.1
  • 48
    • 18444379345 scopus 로고    scopus 로고
    • Local aromaticities in large polyacene molecules
    • Aihara J.-I., Kanno H. Local aromaticities in large polyacene molecules. J. Phys. Chem. A 2005, 109:3717-3721.
    • (2005) J. Phys. Chem. A , vol.109 , pp. 3717-3721
    • Aihara, J.-I.1    Kanno, H.2
  • 49
    • 33845202357 scopus 로고    scopus 로고
    • Local aromaticity in polycyclic aromatic hydro-carbons: electron delocalization versus magnetic indices
    • Bultinck P., Fias S., Ponec R. Local aromaticity in polycyclic aromatic hydro-carbons: electron delocalization versus magnetic indices. Chem. Eur. J. 2006, 12:8813-8818.
    • (2006) Chem. Eur. J. , vol.12 , pp. 8813-8818
    • Bultinck, P.1    Fias, S.2    Ponec, R.3
  • 50
    • 34249737061 scopus 로고    scopus 로고
    • Planar mono-, di- aza- and phospha-naphthalene: structure and aromaticity
    • Wang L., Wang H. Planar mono-, di- aza- and phospha-naphthalene: structure and aromaticity. Int. J. Quantum Chem. 2007, 107:846-1855.
    • (2007) Int. J. Quantum Chem. , vol.107 , pp. 846-1855
    • Wang, L.1    Wang, H.2
  • 51
    • 22544482677 scopus 로고    scopus 로고
    • Multicenter bond indices as a new measure of aromaticity in polycyclic aromatic hydrocarbons
    • Bultinck P., Ponec R., van Damme S. Multicenter bond indices as a new measure of aromaticity in polycyclic aromatic hydrocarbons. J. Phys. Org. Chem. 2005, 18:706-718.
    • (2005) J. Phys. Org. Chem. , vol.18 , pp. 706-718
    • Bultinck, P.1    Ponec, R.2    van Damme, S.3
  • 52
    • 22944465467 scopus 로고    scopus 로고
    • The aromatic fluctuation index (FLU): a new aromaticity index based on electron delocalization
    • Matito E., Duran M., Solà M. The aromatic fluctuation index (FLU): a new aromaticity index based on electron delocalization. J. Chem. Phys. 2005, 122:014109.
    • (2005) J. Chem. Phys. , vol.122 , pp. 014109
    • Matito, E.1    Duran, M.2    Solà, M.3
  • 54
    • 1642576743 scopus 로고    scopus 로고
    • Graphical linking of MO multicenter bond index and VB structures. II - 5-c rings and 6-c heterocyclic rings
    • Bollini C.G., Giambiagi M., de Giambiagi M.S., de Figuereido A.P. Graphical linking of MO multicenter bond index and VB structures. II - 5-c rings and 6-c heterocyclic rings. Struct. Chem. 2001, 12:113-120.
    • (2001) Struct. Chem. , vol.12 , pp. 113-120
    • Bollini, C.G.1    Giambiagi, M.2    de Giambiagi, M.S.3    de Figuereido, A.P.4
  • 55
    • 23844455882 scopus 로고    scopus 로고
    • Multicenter bond indices as a new means for the quantitative characterization of homoaromaticity
    • Ponec R., Bultinck P., Saliner A.G. Multicenter bond indices as a new means for the quantitative characterization of homoaromaticity. J. Phys. Chem. A 2005, 109:6606-6609.
    • (2005) J. Phys. Chem. A , vol.109 , pp. 6606-6609
    • Ponec, R.1    Bultinck, P.2    Saliner, A.G.3
  • 56
    • 33745794688 scopus 로고    scopus 로고
    • Electron delocalization and aromaticity in linear polyacenes: atoms in molecules multicenter delocalization index
    • Bultinck P., Rafat M., Ponec R., van Gheluwe B., Carbó-Dorca R., Popelier P. Electron delocalization and aromaticity in linear polyacenes: atoms in molecules multicenter delocalization index. J. Phys. Chem. A 2006, 110:7642-7648.
    • (2006) J. Phys. Chem. A , vol.110 , pp. 7642-7648
    • Bultinck, P.1    Rafat, M.2    Ponec, R.3    van Gheluwe, B.4    Carbó-Dorca, R.5    Popelier, P.6
  • 57
    • 33846647429 scopus 로고    scopus 로고
    • QTAIM n-center delocalization indices as descriptors of aromaticity in mono and polyheterocycles
    • Mandado M., González Moa M.J., Mosquera R.A. QTAIM n-center delocalization indices as descriptors of aromaticity in mono and polyheterocycles. J. Comput. Chem. 2007, 28:127-136.
    • (2007) J. Comput. Chem. , vol.28 , pp. 127-136
    • Mandado, M.1    González Moa, M.J.2    Mosquera, R.A.3
  • 59
    • 84555165565 scopus 로고    scopus 로고
    • AIM 2000, Version 2.0, Ontario, Canada, McMaster University.
    • R.F.W. Bader, AIM 2000, Version 2.0, Ontario, Canada, McMaster University, 2002.
    • (2002)
    • Bader, R.F.W.1
  • 60
    • 46449115855 scopus 로고    scopus 로고
    • On the performance of some aromaticity indices: a critical assessment using a test set
    • Feixas F., Matito E., Poater J., Sola M. On the performance of some aromaticity indices: a critical assessment using a test set. J. Comput. Chem. 2008, 29:1543-1554.
    • (2008) J. Comput. Chem. , vol.29 , pp. 1543-1554
    • Feixas, F.1    Matito, E.2    Poater, J.3    Sola, M.4
  • 61
    • 33845876604 scopus 로고    scopus 로고
    • Electron sharing indexes at the correlated level. Application to aromaticity calculations
    • Matito E., Solà M., Salvador P., Duran M. Electron sharing indexes at the correlated level. Application to aromaticity calculations. Faraday Discuss. 2007, 135:325-345.
    • (2007) Faraday Discuss. , vol.135 , pp. 325-345
    • Matito, E.1    Solà, M.2    Salvador, P.3    Duran, M.4
  • 62
    • 27744578989 scopus 로고    scopus 로고
    • Energetic aspects of cyclic pi-electron delocalization: evaluation of the methods of estimating aromatic stabilization energies
    • Cyrański M.K. Energetic aspects of cyclic pi-electron delocalization: evaluation of the methods of estimating aromatic stabilization energies. Chem. Rev. 2005, 105:3773-3811.
    • (2005) Chem. Rev. , vol.105 , pp. 3773-3811
    • Cyrański, M.K.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.