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Volumn 17, Issue 8, 2011, Pages 2017-2027

A new approach for aromaticity criterion based on electrostatic field gradient

Author keywords

Aromaticity; EFG; Electrostatic field gradient

Indexed keywords

ORGANIC COMPOUND;

EID: 80051799732     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-010-0902-6     Document Type: Article
Times cited : (11)

References (62)
  • 1
    • 0035353539 scopus 로고    scopus 로고
    • Measuring aromaticity by NMR
    • DOI 10.1021/cr990359+
    • RH Mitchell 2001 Chem Rev 101 1301 1315 10.1021/cr990359+ 1:CAS:528:DC%2BD3MXhslagsLc%3D (Pubitemid 35373003)
    • (2001) Chemical Reviews , vol.101 , Issue.5 , pp. 1301-1315
    • Mitchell, R.H.1
  • 6
    • 0347477024 scopus 로고    scopus 로고
    • In Discrete Mathematics of Molecules Harwod, Chichester, England
    • Rouvray DH, King RB (2002) Topology in Chemistry. In: Discrete Mathematics of Molecules, Harwod, Chichester, England
    • (2002) Topology in Chemistry
    • Rouvray, D.H.1    King, R.B.2
  • 8
    • 0141789719 scopus 로고    scopus 로고
    • 10.1021/cr9903656 1:CAS:528:DC%2BD3sXlslKms7o%3D
    • M Randic 2003 Chem Rev 103 3449 3606 10.1021/cr9903656 1:CAS:528:DC%2BD3sXlslKms7o%3D
    • (2003) Chem Rev , vol.103 , pp. 3449-3606
    • Randic, M.1
  • 10
    • 33745219901 scopus 로고    scopus 로고
    • V, Zubatyuk R I, Grob L, Leszczynski J
    • 10.1016/j.molstruc.2006.01.019 1:CAS:528:DC%2BD28XmsVyisbg%3D
    • OV Shishkin IV Omelchenko M Krasovska 2006 V, Zubatyuk R I, Grob L, Leszczynski J J Mol Struct 791 158 164 10.1016/j.molstruc.2006.01.019 1:CAS:528:DC%2BD28XmsVyisbg%3D
    • (2006) J Mol Struct , vol.791 , pp. 158-164
    • Shishkin, O.V.1    Omelchenko, I.V.2    Krasovska, M.3
  • 11
    • 27544510655 scopus 로고
    • 1:CAS:528:DyaK3sXlvFSntw%3D%3D
    • TM Krygowski 1993 J Chem Inf Comput Sci 33 70 78 1:CAS:528: DyaK3sXlvFSntw%3D%3D
    • (1993) J Chem Inf Comput Sci , vol.33 , pp. 70-78
    • Krygowski, T.M.1
  • 12
    • 33751158301 scopus 로고
    • Giambiagi MSd
    • 10.1021/j100075a013 1:CAS:528:DyaK2cXktFygsbw%3D
    • KC Mundim M Giambiagi 1994 Giambiagi MSd J Phys Chem 98 6118 6119 10.1021/j100075a013 1:CAS:528:DyaK2cXktFygsbw%3D
    • (1994) J Phys Chem , vol.98 , pp. 6118-6119
    • Mundim, K.C.1    Giambiagi, M.2
  • 16
    • 0034254102 scopus 로고    scopus 로고
    • 10.1039/b002009p 1:CAS:528:DC%2BD3cXltVyrt7k%3D
    • M Giambiagi MSd Giambiagi CDdS Silva APd Figueiredo 2000 Phys Chem Chem Phys 2 3381 3392 10.1039/b002009p 1:CAS:528:DC%2BD3cXltVyrt7k%3D
    • (2000) Phys Chem Chem Phys , vol.2 , pp. 3381-3392
    • Giambiagi, M.1    Msd, G.2    Cdds, S.3    Apd, F.4
  • 17
    • 34547241472 scopus 로고    scopus 로고
    • Chemical graph theory and n-center electron delocalization indices: A study on polycyclic aromatic hydrocarbons
    • DOI 10.1002/jcc.20647
    • M Mandado M Gonzalez-Moa RA Mosquera 2007 J Comput Chem 28 1625 1633 10.1002/jcc.20647 1:CAS:528:DC%2BD2sXmsFekt7s%3D (Pubitemid 47146538)
    • (2007) Journal of Computational Chemistry , vol.28 , Issue.10 , pp. 1625-1633
    • Mandado, M.1    Gonzalez-Moa, M.J.2    Mosquera, R.A.3
  • 18
    • 33845416380 scopus 로고    scopus 로고
    • Multicenter delocalization indices vs. properties of the electron density at ring critical points: A study on polycyclic aromatic hydrocarbons
    • DOI 10.1016/j.cplett.2006.11.009, PII S000926140601654X
    • M Mandado P Bultinck M Gonzalez-Moa RA Mosquera 2006 Chem Phys Lett 433 5 9 10.1016/j.cplett.2006.11.009 1:CAS:528:DC%2BD28Xhtlaiu7zJ (Pubitemid 44889248)
    • (2006) Chemical Physics Letters , vol.433 , Issue.1-3 , pp. 5-9
    • Mandado, M.1    Bultinck, P.2    Gonzalez-Moa, M.J.3    Mosquera, R.A.4
  • 19
    • 33846647429 scopus 로고    scopus 로고
    • QTAIM N-center delocalization indices as descriptors of aromaticity in mono and poly heterocycles
    • DOI 10.1002/jcc.20468
    • M Mandado MJ Gonzalez-Moa RA Mosquera 2007 J Comput Chem 28 127 136 10.1002/jcc.20468 1:CAS:528:DC%2BD2sXktVKgsw%3D%3D (Pubitemid 46180482)
    • (2007) Journal of Computational Chemistry , vol.28 , Issue.1 , pp. 127-136
    • Mandado, M.1    Gonzalez-Moa, M.J.2    Mosquera, R.A.3
  • 20
    • 33646388391 scopus 로고    scopus 로고
    • 10.1021/jp057387i 1:CAS:528:DC%2BD28XivVeltb0%3D
    • E Matito P Salvador M Duran M Sola 2006 J Phys Chem A 110 5108 5113 10.1021/jp057387i 1:CAS:528:DC%2BD28XivVeltb0%3D
    • (2006) J Phys Chem A , vol.110 , pp. 5108-5113
    • Matito, E.1    Salvador, P.2    Duran, M.3    Sola, M.4
  • 21
    • 46449115855 scopus 로고    scopus 로고
    • 10.1002/jcc.20914 1:CAS:528:DC%2BD1cXnvFCgur4%3D
    • F Feixas E Matito J Poater M Sola 2008 J Comput Chem 29 1543 1554 10.1002/jcc.20914 1:CAS:528:DC%2BD1cXnvFCgur4%3D
    • (2008) J Comput Chem , vol.29 , pp. 1543-1554
    • Feixas, F.1    Matito, E.2    Poater, J.3    Sola, M.4
  • 22
    • 33750347300 scopus 로고    scopus 로고
    • Analysis of electron delocalization in aromatic systems: Individual molecular orbital contributions to Para-Delocalization Indexes (PDI)
    • DOI 10.1021/jp0631329
    • M Güell E Matito JM Luis J Poater M Sola 2006 J Phys Chem A 110 11569 11574 10.1021/jp0631329 (Pubitemid 44626488)
    • (2006) Journal of Physical Chemistry A , vol.110 , Issue.40 , pp. 11569-11574
    • Guell, M.1    Matito, E.2    Luis, J.M.3    Poater, J.4    Sola, M.5
  • 23
    • 0037455221 scopus 로고    scopus 로고
    • 10.1002/chem.200390041 1:CAS:528:DC%2BD3sXnvFCkuw%3D%3D
    • J Poater X Fradera M Duran M Sola 2003 Chem Eur J 9 400 406 10.1002/chem.200390041 1:CAS:528:DC%2BD3sXnvFCkuw%3D%3D
    • (2003) Chem Eur J , vol.9 , pp. 400-406
    • Poater, J.1    Fradera, X.2    Duran, M.3    Sola, M.4
  • 24
    • 23844455882 scopus 로고    scopus 로고
    • Multicenter bond indices as a new means for the quantitative characterization of homoaromaticity
    • DOI 10.1021/jp052179b
    • R Ponec P Bultinck A Gallegos-Saliner 2005 J Phys Chem A 109 6606 6609 10.1021/jp052179b 1:CAS:528:DC%2BD2MXls1ajt7k%3D (Pubitemid 41163159)
    • (2005) Journal of Physical Chemistry A , vol.109 , Issue.29 , pp. 6606-6609
    • Ponec, R.1    Bultinck, P.2    Saliner, A.G.3
  • 25
    • 0037455221 scopus 로고    scopus 로고
    • 10.1002/chem.200390041 1:CAS:528:DC%2BD3sXnvFCkuw%3D%3D
    • J Poater X Fradera M Duran M Sola 2003 Eur J Chem 9 400 406 10.1002/chem.200390041 1:CAS:528:DC%2BD3sXnvFCkuw%3D%3D
    • (2003) Eur J Chem , vol.9 , pp. 400-406
    • Poater, J.1    Fradera, X.2    Duran, M.3    Sola, M.4
  • 27
    • 22544482677 scopus 로고    scopus 로고
    • Multicenter bond indices as a new measure of aromaticity in polycyclic aromatic hydrocarbons
    • DOI 10.1002/poc.922
    • P Bultinck R Ponec SV Damme 2005 J Phys Org Chem 18 706 718 10.1002/poc.922 1:CAS:528:DC%2BD2MXmslCqsb4%3D (Pubitemid 41013081)
    • (2005) Journal of Physical Organic Chemistry , vol.18 , Issue.8 , pp. 706-718
    • Bultinck, P.1    Ponec, R.2    Van Damme, S.3
  • 28
    • 0010762104 scopus 로고
    • 10.1007/BF01339530
    • EZ Hückel 1931 Phys 70 204 286 10.1007/BF01339530
    • (1931) Phys , vol.70 , pp. 204-286
    • Hückel, E.Z.1
  • 29
    • 0012236925 scopus 로고
    • 10.1007/BF01341936
    • EZ Hückel 1932 Phys 76 628 648 10.1007/BF01341936
    • (1932) Phys , vol.76 , pp. 628-648
    • Hückel, E.Z.1
  • 30
    • 34547528768 scopus 로고    scopus 로고
    • Properties of aromaticity indices based on the one-electron density matrix
    • DOI 10.1021/jp0716132
    • J Cioslowski E Matito M Sola 2007 J Phys Chem A 111 6521 6525 10.1021/jp0716132 1:CAS:528:DC%2BD2sXms1CisLs%3D (Pubitemid 47184355)
    • (2007) Journal of Physical Chemistry A , vol.111 , Issue.28 , pp. 6521-6525
    • Cioslowski, J.1    Matito, E.2    Sola, M.3
  • 31
    • 27744550549 scopus 로고    scopus 로고
    • Introduction: Delocalization - Pi and Sigma
    • DOI 10.1021/cr030095y
    • S PvR 2005 Chem Rev 105 3433 3435 10.1021/cr030095y (Pubitemid 41622390)
    • (2005) Chemical Reviews , vol.105 , Issue.10 , pp. 3433-3435
    • Von Rague Schleyer, P.1
  • 33
    • 0035353481 scopus 로고    scopus 로고
    • Aromaticity: Introduction
    • DOI 10.1021/cr0103221
    • S PvR 2001 Chem Rev 101 1115 1117 10.1021/cr0103221 (Pubitemid 35372996)
    • (2001) Chemical Reviews , vol.101 , Issue.5 , pp. 1115-1117
    • Von Rague Schleyer, P.1
  • 35
    • 0034650096 scopus 로고    scopus 로고
    • 10.1016/S0301-0104(99)00342-0 1:CAS:528:DC%2BD3cXhsFCgu74%3D
    • W Bailey 2000 Chem Phys 252 57 66 10.1016/S0301-0104(99)00342-0 1:CAS:528:DC%2BD3cXhsFCgu74%3D
    • (2000) Chem Phys , vol.252 , pp. 57-66
    • Bailey, W.1
  • 36
    • 2542500632 scopus 로고    scopus 로고
    • 10.1016/j.cplett.2004.04.065 1:CAS:528:DC%2BD2cXksValsbw%3D
    • SK Amini NL Hadipour F Elmi 2004 Chem Phys Lett 391 95 100 10.1016/j.cplett.2004.04.065 1:CAS:528:DC%2BD2cXksValsbw%3D
    • (2004) Chem Phys Lett , vol.391 , pp. 95-100
    • Amini, S.K.1    Hadipour, N.L.2    Elmi, F.3
  • 37
    • 14844344040 scopus 로고    scopus 로고
    • 2H nuclear quadrupole coupling constants
    • DOI 10.1021/jp046216v
    • F Elmi NL Hadipour 2005 J Phys Chem A 109 1729 1733 10.1021/jp046216v 1:CAS:528:DC%2BD2MXps1Oitg%3D%3D (Pubitemid 40352368)
    • (2005) Journal of Physical Chemistry A , vol.109 , Issue.8 , pp. 1729-1733
    • Elmi, F.1    Hadipour, N.L.2
  • 39
    • 0345491105 scopus 로고
    • 10.1103/PhysRevB.37.785 1:CAS:528:DyaL1cXktFWrtbw%3D
    • C Lee W Yang RG Parr 1988 Phys Rev B 37 785 789 10.1103/PhysRevB.37.785 1:CAS:528:DyaL1cXktFWrtbw%3D
    • (1988) Phys Rev B , vol.37 , pp. 785-789
    • Lee, C.1    Yang, W.2    Parr, R.G.3
  • 40
    • 1242346134 scopus 로고    scopus 로고
    • Gaussian Inc Pittsburgh, PA
    • Frisch MJ et al. (2003) Gaussian03. Gaussian Inc, Pittsburgh, PA
    • (2003) Gaussian03
    • Frisch, M.J.1
  • 44
    • 10944250135 scopus 로고    scopus 로고
    • 1:CAS:528:DC%2BD2cXhtFShtL7P
    • TM Krygowski BT Stepien 2004 J Pol Chem 78 2213 2217 1:CAS:528: DC%2BD2cXhtFShtL7P
    • (2004) J Pol Chem , vol.78 , pp. 2213-2217
    • Krygowski, T.M.1    Stepien, B.T.2
  • 45
    • 27744449419 scopus 로고    scopus 로고
    • Sigma- and Pi-electron delocalization: Focus on substituent effects
    • DOI 10.1021/cr030081s
    • TM Krygowski BT Stepien 2005 Chem Rev 105 3482 3512 10.1021/cr030081s 1:CAS:528:DC%2BD2MXns1aju7c%3D (Pubitemid 41622392)
    • (2005) Chemical Reviews , vol.105 , Issue.10 , pp. 3482-3512
    • Krygowski, T.M.1    Stepien, B.T.2
  • 48
    • 27744578989 scopus 로고    scopus 로고
    • Energetic aspects of cyclic pi-electron delocalization: Evaluation of the methods of estimating aromatic stabilization energies
    • DOI 10.1021/cr0300845
    • MK Cyranski 2005 Chem Rev 105 3773 3811 10.1021/cr0300845 1:CAS:528:DC%2BD2MXps1eqsrs%3D (Pubitemid 41622398)
    • (2005) Chemical Reviews , vol.105 , Issue.10 , pp. 3773-3811
    • Cyranski, M.K.1
  • 49
    • 28944446092 scopus 로고    scopus 로고
    • A novel approach in analyzing aromaticity by homo- And isostructural reactions: An ab initio study of fluorobenzenes
    • DOI 10.1021/jp0532871
    • D Baric B Kovacevic ZB Maksic T Muller 2005 J Phys Chem A 109 10594 10606 10.1021/jp0532871 1:CAS:528:DC%2BD2MXhtFKltbfI (Pubitemid 41784861)
    • (2005) Journal of Physical Chemistry A , vol.109 , Issue.46 , pp. 10594-10606
    • Baric, D.1    Kovacevic, B.2    Maksic, Z.B.3    Muller, T.4
  • 50
    • 67049137355 scopus 로고    scopus 로고
    • Schleyer PvR, Puchta R, Kiran B, Mauksch M, Hommes NJRvE, Alkorta i
    • 10.1021/jp902983r 1:CAS:528:DC%2BD1MXmsVegt7s%3D
    • JI Wu FG Puhlhofer 2009 Schleyer PvR, Puchta R, Kiran B, Mauksch M, Hommes NJRvE, Alkorta I J Phys Chem A 113 6789 6794 10.1021/jp902983r 1:CAS:528:DC%2BD1MXmsVegt7s%3D
    • (2009) J Phys Chem A , vol.113 , pp. 6789-6794
    • Wu, J.I.1    Puhlhofer, F.G.2
  • 51
    • 0034254102 scopus 로고    scopus 로고
    • Giambiagi MSd, Silva CDdS, Figueiredo Apd
    • 10.1039/b002009p 1:CAS:528:DC%2BD3cXltVyrt7k%3D
    • M Giambiagi 2000 Giambiagi MSd, Silva CDdS, Figueiredo Apd Phys Chem Chem Phys 2 3381 3392 10.1039/b002009p 1:CAS:528:DC%2BD3cXltVyrt7k%3D
    • (2000) Phys Chem Chem Phys , vol.2 , pp. 3381-3392
    • Giambiagi, M.1
  • 52
    • 0000698646 scopus 로고
    • 10.1021/ja00175a005 1:CAS:528:DyaK3cXltlWhtbo%3D
    • K Jug AM Koster 1990 J Am Chem Soc 112 6772 6777 10.1021/ja00175a005 1:CAS:528:DyaK3cXltlWhtbo%3D
    • (1990) J Am Chem Soc , vol.112 , pp. 6772-6777
    • Jug, K.1    Koster, A.M.2
  • 53
    • 33845551526 scopus 로고
    • 10.1021/jo00156a038 1:CAS:528:DyaL3sXhsF2rsb4%3D
    • K Jug 1983 J Org Chem 48 1344 1348 10.1021/jo00156a038 1:CAS:528:DyaL3sXhsF2rsb4%3D
    • (1983) J Org Chem , vol.48 , pp. 1344-1348
    • Jug, K.1
  • 54
    • 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
    • DOI 10.1016/j.tet.2006.10.022, PII S0040402006016413
    • M Mandado N Otero RA Mosquera 2006 Tetrahedron 62 12204 12210 10.1016/j.tet.2006.10.022 1:CAS:528:DC%2BD28Xht1CmsbfN (Pubitemid 44738957)
    • (2006) Tetrahedron , vol.62 , Issue.52 , pp. 12204-12210
    • Mandado, M.1    Otero, N.2    Mosquera, R.A.3
  • 55
    • 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
    • DOI 10.1021/cr030085x
    • J Poater M Duran M Sola B Silvi 2005 Chem Rev 105 3911 3947 10.1021/cr030085x 1:CAS:528:DC%2BD2MXmtVChtbc%3D (Pubitemid 41630339)
    • (2005) Chemical Reviews , vol.105 , Issue.10 , pp. 3911-3947
    • Poater, J.1    Duran, M.2    Sola, M.3    Silvi, B.4
  • 57
    • 44649159599 scopus 로고    scopus 로고
    • 10.1016/j.cplett.2008.04.122 1:CAS:528:DC%2BD1cXmvFOnur8%3D
    • A Mohajeri A Ashrafi 2008 Chem Phys Lett 458 378 10.1016/j.cplett.2008. 04.122 1:CAS:528:DC%2BD1cXmvFOnur8%3D
    • (2008) Chem Phys Lett , vol.458 , pp. 378
    • Mohajeri, A.1    Ashrafi, A.2
  • 58
    • 0000440196 scopus 로고    scopus 로고
    • 10.1002/(SICI)1097-461X(1998)70: 3<503::AID-QUA6>3.0.CO;2-Y 1:CAS:528:DyaK1cXmslKhs78%3D
    • Y Anusooya A Chakrabarti SK Pati S Ramasesha 1998 Int J Quantum Chem 70 503 10.1002/(SICI)1097-461X(1998)70:3<503::AID-QUA6>3.0.CO;2-Y 1:CAS:528:DyaK1cXmslKhs78%3D
    • (1998) Int J Quantum Chem , vol.70 , pp. 503
    • Anusooya, Y.1    Chakrabarti, A.2    Pati, S.K.3    Ramasesha, S.4
  • 59
    • 0038707940 scopus 로고    scopus 로고
    • The relation between endohedral chemical shifts and local aromaticities in fullerenes
    • DOI 10.1002/(SICI)1521-3765(19980416)4: 4<734::AID-CHEM734>3.0. CO;2-C
    • M Buhl 1998 Eur J Chem 4 734 739 10.1002/(SICI)1521-3765(19980416)4: 4<734::AID-CHEM734>3.0.CO;2-C 1:CAS:528:DyaK1cXjtVyqt7c%3D (Pubitemid 28286178)
    • (1998) Chemistry - A European Journal , vol.4 , Issue.4 , pp. 734-739
    • Buhl, M.1
  • 61
    • 3142572766 scopus 로고    scopus 로고
    • 10.1016/j.cplett.2004.05.122 1:CAS:528:DC%2BD2cXlsFKgtLk%3D
    • J Aihara 2004 Chem Phys Lett 393 7 11 10.1016/j.cplett.2004.05.122 1:CAS:528:DC%2BD2cXlsFKgtLk%3D
    • (2004) Chem Phys Lett , vol.393 , pp. 7-11
    • Aihara, J.1
  • 62
    • 23644454377 scopus 로고    scopus 로고
    • An analysis of the changes in aromaticity and planarity along the reaction path of the simplest Diels-Alder reaction. Exploring the validity of different indicators of aromaticity
    • DOI 10.1016/j.theochem.2005.02.020, PII S0166128005001491
    • E Matito J Poater M Duran M Sola 2005 J Mol Struct Theochem 727 165 171 10.1016/j.theochem.2005.02.020 1:CAS:528:DC%2BD2MXot1Cjtbw%3D (Pubitemid 41133249)
    • (2005) Journal of Molecular Structure: THEOCHEM , vol.727 , Issue.1-3 SPEC. ISS. , pp. 165-171
    • Matito, E.1    Poater, J.2    Duran, M.3    Sola, M.4


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