메뉴 건너뛰기




Volumn 17, Issue 2, 2012, Pages 1335-1353

Understanding the mechanism of the intramolecular stetter reaction. A DFT study

Author keywords

DFT calculations; Intramolecular Michael addition; Intramolecular Stetter reaction; Mechanisms; N heterocyclic carbenes; Organocatalysis; Umpolung reactivity

Indexed keywords

CARBENE; DRUG DERIVATIVE; HETEROCYCLIC COMPOUND; METHANE;

EID: 84857598542     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17021335     Document Type: Article
Times cited : (38)

References (82)
  • 1
    • 56549104231 scopus 로고    scopus 로고
    • Recent advances in carbon-carbon bond-forming reactions involving homoenolates generated by NHC catalysis
    • Nair, V.; Vellalath, S.; Babu, B.P. Recent advances in carbon-carbon bond-forming reactions involving homoenolates generated by NHC catalysis. Chem. Soc. Rev. 2008, 37, 2691-2698.
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 2691-2698
    • Nair, V.1    Vellalath, S.2    Babu, B.P.3
  • 2
    • 38349109278 scopus 로고    scopus 로고
    • Organocatalysis by N-heterocyclic carbenes
    • Enders, D.; Niemeier, O.; Henseler, A. Organocatalysis by N-heterocyclic carbenes. Chem. Rev. 2007, 107, 5606-5655.
    • (2007) Chem. Rev. , vol.107 , pp. 5606-5655
    • Enders, D.1    Niemeier, O.2    Henseler, A.3
  • 4
    • 79960213720 scopus 로고    scopus 로고
    • N-Heterocyclic carbenes as organic catalysts
    • Díez-González, S., Ed.; The Royal Society of Chemistry: Cambridge, UK; Chapter 14
    • Chiang, P.-C.; Bode, J.W. N-Heterocyclic carbenes as organic catalysts. In N-Heterocyclic Carbenes, Díez-González, S., Ed.; The Royal Society of Chemistry: Cambridge, UK, 2011; Chapter 14, pp. 399-435.
    • (2011) N-Heterocyclic Carbenes , pp. 399-435
    • Chiang, P.-C.1    Bode, J.W.2
  • 5
    • 78649374767 scopus 로고    scopus 로고
    • Asymmetric organocatalysis
    • Moore, J.L.; Rovis, T. Asymmetric organocatalysis. Top. Curr. Chem. 2011, 291, 77-144.
    • (2011) Top. Curr. Chem. , vol.291 , pp. 77-144
    • Moore, J.L.1    Rovis, T.2
  • 6
    • 79958213157 scopus 로고    scopus 로고
    • Asymmetric N-heterocyclic carbene (NHC) catalyzed acyl anion reactions
    • Vora, H.U.; Rovis, T. Asymmetric N-heterocyclic carbene (NHC) catalyzed acyl anion reactions. Aldrichimica Acta 2010, 44, 3-11.
    • (2010) Aldrichimica Acta , vol.44 , pp. 3-11
    • Vora, H.U.1    Rovis, T.2
  • 7
    • 0036263823 scopus 로고    scopus 로고
    • An efficient nucleophilic carbene catalyst for the asymmetric benzoin condensation. N-Heterocyclic carbene-catalyzed generation of homoenolates: γ-Butyrolactones by direct annulations of enals and aldehydes
    • Enders, D.; Kallfass, U. An efficient nucleophilic carbene catalyst for the asymmetric benzoin condensation. N-Heterocyclic carbene-catalyzed generation of homoenolates: γ-Butyrolactones by direct annulations of enals and aldehydes. Angew. Chem. Int. Ed. 2002, 41, 1743-1745.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1743-1745
    • Enders, D.1    Kallfass, U.2
  • 8
    • 7744232978 scopus 로고    scopus 로고
    • N-heterocyclic carbene-catalyzed generation of homoenolates: γ-butyrolactones by direct annulations of enals and aldehydes
    • DOI 10.1021/ja044714b
    • Sohn, S.S.; Rosen, E.L.; Bode, J.W. N-Heterocyclic carbene-catalyzed generation of homoenolates: γ-Butyrolactones by direct annulations of enals and aldehydes. J. Am. Chem. Soc. 2004, 126, 14370-14371. (Pubitemid 39463617)
    • (2004) Journal of the American Chemical Society , vol.126 , Issue.44 , pp. 14370-14371
    • Sohn, S.S.1    Rosen, E.L.2    Bode, J.W.3
  • 9
    • 10044249952 scopus 로고    scopus 로고
    • Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ-butyrolactones
    • DOI 10.1002/anie.200461572
    • Burstein, C.; Glorius, F. Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ- butyrolactones. Angew. Chem. Int. Ed. 2004, 6205-6208. (Pubitemid 39611895)
    • (2004) Angewandte Chemie - International Edition , vol.43 , Issue.45 , pp. 6205-6208
    • Burstein, C.1    Glorius, F.2
  • 10
    • 0038375618 scopus 로고    scopus 로고
    • Catalytic intramolecular crossed aldehyde-ketone benzoin reactions: A novel synthesis of functionalized preanthraquinones
    • DOI 10.1021/ja035308f
    • Hachisu, Y.; Bode, J.W.; Suzuki, K. Catalytic intramolecular crossed aldehyde-ketone benzoin reactions: A novel synthesis of functionalized preanthraquinones. J. Am. Chem. Soc. 2003, 125, 8432-8433. (Pubitemid 36858402)
    • (2003) Journal of the American Chemical Society , vol.125 , Issue.28 , pp. 8432-8433
    • Hachisu, Y.1    Bode, J.W.2    Suzuki, K.3
  • 11
    • 34547424960 scopus 로고    scopus 로고
    • Modified chiral triazolium salts for enantioselective benzoin cyclization of enolizable keto-aldehydes: Synthesis of (+)-Sappanone B
    • Takikawa, H.; Suzuki, K. Modified chiral triazolium salts for enantioselective benzoin cyclization of enolizable keto-aldehydes: Synthesis of (+)-Sappanone B. Org. Lett. 2007, 9, 2713-2716.
    • (2007) Org. Lett. , vol.9 , pp. 2713-2716
    • Takikawa, H.1    Suzuki, K.2
  • 12
    • 33745722719 scopus 로고    scopus 로고
    • Catalytic enantioselective crossed aldehyde-ketone benzoin cyclization
    • DOI 10.1002/anie.200600268
    • Takikawa, H.; Hachisu, Y.; Bode, J.W.; Suzuki, K. Catalytic enantioselective crossed aldehydeketone benzoin cyclization. Angew. Chem. Int. Ed. 2006, 45, 3492-3494. (Pubitemid 44098965)
    • (2006) Angewandte Chemie - International Edition , vol.45 , Issue.21 , pp. 3492-3494
    • Takikawa, H.1    Hachisu, Y.2    Bode, J.W.3    Suzuki, K.4
  • 13
    • 33745716505 scopus 로고    scopus 로고
    • Asymmetric intramolecular crossed-benzoin reactions by N-heterocyclic carbene catalysis
    • DOI 10.1002/anie.200503885
    • Enders, D.; Niemeier, O.; Balensiefer, T. Asymmetric intramolecular crossed-benzoin reactions by N-heterocyclic carbene catalysis. Angew. Chem. Int. Ed. 2006, 45, 1463-1467. (Pubitemid 44097635)
    • (2006) Angewandte Chemie - International Edition , vol.45 , Issue.9 , pp. 1463-1467
    • Enders, D.1    Niemeier, O.2    Balensiefer, T.3
  • 14
    • 33746584001 scopus 로고    scopus 로고
    • N-heterocyclic carbene-catalyzed conjugate umpolung for the synthesis of γ-butyrolactones
    • DOI 10.1055/s-2006-942447
    • Burstein, C.; Tschan, S.; Xie, X.L.; Glorius, F. N-heterocyclic carbene-catalyzed conjugate umpolung for the synthesis of gamma-butyrolactones. Synthesis 2006, 2418-2439. (Pubitemid 44146995)
    • (2006) Synthesis , Issue.14 , pp. 2418-2439
    • Burstein, C.1    Tschan, S.2    Xie, X.3    Glorius, F.4
  • 15
    • 33846925017 scopus 로고    scopus 로고
    • Investigating organocatalytic reactions: Mass spectrometric studies of a conjugate umpolung reaction
    • DOI 10.1039/b613862d
    • Schrader, W.; Handayani, P.P.; Burstein, C.; Glorius, F. Investigating organocatalytic reactions: Mass spectrometric studies of a conjugate umpolung reaction. Chem. Commun. 2007, 716-718. (Pubitemid 46233540)
    • (2007) Chemical Communications , Issue.7 , pp. 716-718
    • Schrader, W.1    Handayani, P.P.2    Burstein, C.3    Glorius, F.4
  • 16
    • 53849128873 scopus 로고    scopus 로고
    • Diastereoselective synthesis of trifluoromethylated γ- butyrolactones via N-heterocyclic carbene-catalyzed conjugated umpolung of α,β-unsaturated aldehydes
    • Hirano, K.; Piel, I.; Glorius, F. Diastereoselective synthesis of trifluoromethylated γ-butyrolactones via N-heterocyclic carbene-catalyzed conjugated umpolung of α,β-unsaturated aldehydes. Adv. Synth. Catal. 2008, 350, 984-988.
    • (2008) Adv. Synth. Catal. , vol.350 , pp. 984-988
    • Hirano, K.1    Piel, I.2    Glorius, F.3
  • 17
    • 32644452625 scopus 로고    scopus 로고
    • N-heterocyclic carbene catalyzed reaction of enals and 1,2-dicarbonyl compounds: Stereoselective synthesis of spiro γ-butyrolactones
    • DOI 10.1021/ol052926n
    • Nair, V.; Vellalath, S.; Poonoth, M.; Mohan, R.; Suresh, E. N-Heterocyclic carbene catalyzed reaction of enals and 1,2-dicarbonyl compounds: Stereoselective synthesis of spiro γ-butyrolactones. Org. Lett. 2006, 8, 507-509. (Pubitemid 43241697)
    • (2006) Organic Letters , vol.8 , Issue.3 , pp. 507-509
    • Nair, V.1    Vellalath, S.2    Poonoth, M.3    Mohan, R.4    Suresh, E.5
  • 18
    • 33646071885 scopus 로고    scopus 로고
    • Hydroacylation of activated ketones catalyzed by N-heterocyclic carbenes
    • Chan, A.; Scheidt, K.A. Hydroacylation of activated ketones catalyzed by N-heterocyclic carbenes. J. Am. Chem. Soc. 2006, 128, 4558-4559.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 4558-4559
    • Chan, A.1    Scheidt, K.A.2
  • 19
    • 13644269271 scopus 로고    scopus 로고
    • Thiazolylalanine-derived catalysts for enantioselective intermolecular aldehyde-imine cross-couplings
    • DOI 10.1021/ja042650z
    • Mennen, S.M.; Gipson, J.D.; Kim, Y.R.; Miller, S. Thiazolylalanine- derived catalysts for enantioselective intermolecular aldehyde-imine cross-couplings. J. Am. Chem. Soc. 2005, 127, 1654-1655. (Pubitemid 40229147)
    • (2005) Journal of the American Chemical Society , vol.127 , Issue.6 , pp. 1654-1655
    • Mennen, S.M.1    Gipson, J.D.2    Kim, Y.R.3    Miller, S.J.4
  • 20
    • 33847076144 scopus 로고    scopus 로고
    • Thiazolium-derived carbene-catalyzed cross-coupling of aldehydes with unactivated imines
    • Li, G.-Q.; Dai, L.-X.; You, S.-L. Thiazolium-derived carbene-catalyzed cross-coupling of aldehydes with unactivated imines. Chem. Commun. 2007, 852-854.
    • (2007) Chem. Commun. , pp. 852-854
    • Li, G.-Q.1    Dai, L.-X.2    You, S.-L.3
  • 21
    • 22244447100 scopus 로고    scopus 로고
    • Catalytic synthesis of γ-lactams via direct annulations of enals and N-sulfonylimines
    • DOI 10.1021/ol051234w
    • He, M.; Bode, J.W. Catalytic synthesis of γ-lactams via direct annulations of enals and N-sulfonylimines. Org. Lett. 2005, 7, 3131-3134. (Pubitemid 40992649)
    • (2005) Organic Letters , vol.7 , Issue.14 , pp. 3131-3134
    • He, M.1    Bode, J.W.2
  • 22
    • 67749124296 scopus 로고    scopus 로고
    • Cyclic ketimines as superior electrophiles for NHCcatalyzed homoenolate additions with broad scope and low catalyst loadings
    • Rommel, M.; Fukuzumi, T.; Bode, J.W. Cyclic ketimines as superior electrophiles for NHCcatalyzed homoenolate additions with broad scope and low catalyst loadings. J. Am. Chem. Soc. 2008, 130, 17266-17267.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 17266-17267
    • Rommel, M.1    Fukuzumi, T.2    Bode, J.W.3
  • 23
    • 18844424752 scopus 로고    scopus 로고
    • New developments in the asymmetric Stetter reaction
    • DOI 10.1002/anie.200500761
    • Christmann, M. New developments in the asymmetric Stetter reaction. Angew. Chem. Int. Ed. 2005, 44, 2632-2634. (Pubitemid 40689564)
    • (2005) Angewandte Chemie - International Edition , vol.44 , Issue.18 , pp. 2632-2634
    • Christmann, M.1
  • 24
    • 67649363846 scopus 로고    scopus 로고
    • The catalytic asymmetric intramolecular Stetter seaction
    • Read de Alaniz, J.; Rovis, T. The catalytic asymmetric intramolecular Stetter seaction. Synlett 2009, 1189-1207.
    • (2009) Synlett , pp. 1189-1207
    • Read De Alaniz, J.1    Rovis, T.2
  • 25
    • 84982417601 scopus 로고
    • Catalyzed addition of aldehydes to activated double bonds - A new synthetic approach
    • Stetter, H. Catalyzed addition of aldehydes to activated double bonds - A new synthetic approach. Angew. Chem. Int. Ed. Engl. 1976, 15, 639-647.
    • (1976) Angew. Chem. Int. Ed. Engl. , vol.15 , pp. 639-647
    • Stetter, H.1
  • 26
    • 84981906064 scopus 로고
    • A new method for addition of aldehydes to activated double bonds
    • Stetter, H.; Schreckenberg, M. A new method for addition of aldehydes to activated double bonds. Angew. Chem. Int. Ed. Engl. 1973, 12, 81.
    • (1973) Angew. Chem. Int. Ed. Engl. , vol.12 , pp. 81
    • Stetter, H.1    Schreckenberg, M.2
  • 27
    • 0001070365 scopus 로고
    • The catalyzed nucleophilic addition of aldehydes to electrophilic double bonds
    • Stetter, H.; Kuhlmann, H. The catalyzed nucleophilic addition of aldehydes to electrophilic double bonds. Org. React. 1991, 40, 407-496.
    • (1991) Org. React. , vol.40 , pp. 407-496
    • Stetter, H.1    Kuhlmann, H.2
  • 28
    • 0001710837 scopus 로고    scopus 로고
    • 157. The first asymmetric intramolecular Stetter reaction. Preliminary communication
    • Enders, D.; Breuer, K.; Runsink, J.; Teles, J.H. The first asymmetric intramolecular Stetter reaction. Preliminary communication. Helv. Chim. Acta 1996, 79, 1899-1902. (Pubitemid 126504187)
    • (1996) Helvetica Chimica Acta , vol.79 , Issue.7 , pp. 1899-1902
    • Enders, D.1    Breuer, K.2    Runsink, J.3    Teles, J.H.4
  • 29
    • 0037019628 scopus 로고    scopus 로고
    • A highly enantioselective catalytic intramolecular stetter reaction
    • DOI 10.1021/ja027411v
    • Kerr, M.S.; Read de Alaniz, J.; Rovis, T. A highly enantioselective catalytic intramolecular Stetter reaction. J. Am. Chem. Soc. 2002, 124, 10298-10299. (Pubitemid 34977382)
    • (2002) Journal of the American Chemical Society , vol.124 , Issue.35 , pp. 10298-10299
    • Kerr, M.S.1    De Alaniz, J.R.2    Rovis, T.3
  • 30
    • 18244367138 scopus 로고    scopus 로고
    • A highly enantio- and diastereoselective catalytic intramolecular Stetter reaction
    • DOI 10.1021/ja0425132
    • Read de Alaniz, J.; Rovis, T. A highly enantio- and diastereoselective catalytic intramolecular Stetter reaction. J. Am. Chem. Soc. 2005, 127, 6284-6289. (Pubitemid 40627752)
    • (2005) Journal of the American Chemical Society , vol.127 , Issue.17 , pp. 6284-6289
    • De Alaniz, J.R.1    Rovis, T.2
  • 31
    • 33644661812 scopus 로고    scopus 로고
    • Asymmetric synthesis of hydrobenzofuranones via desymmetrization of cyclohexadienones using the intramolecular Stetter reaction
    • DOI 10.1021/ja058337u
    • Liu, Q.; Rovis, T. Asymmetric synthesis of hydrobenzofuranones via desymmetrization of cyclohexadienones using the intramolecular Stetter reaction. J. Am. Chem. Soc. 2006, 128, 2552-2553. (Pubitemid 43327929)
    • (2006) Journal of the American Chemical Society , vol.128 , Issue.8 , pp. 2552-2553
    • Liu, Q.1    Rovis, T.2
  • 32
    • 41849101072 scopus 로고    scopus 로고
    • Scope of the asymmetric intramolecular stetter reaction catalyzed by chiral nucleophilic triazolinylidene carbenes
    • DOI 10.1021/jo702313f
    • Read de Alaniz, J.; Kerr, M.S.; Moore, J.L.; Rovis, T. Scope of the asymmetric intramolecular Stetter reaction catalyzed by chiral nucleophilic triazolinylidene carbenes. J. Org. Chem. 2008, 73, 2033-2040. (Pubitemid 351497728)
    • (2008) Journal of Organic Chemistry , vol.73 , Issue.6 , pp. 2033-2040
    • De Alaniz, J.R.1    Kerr, M.S.2    Moore, J.L.3    Rovis, T.4
  • 33
    • 79960063988 scopus 로고    scopus 로고
    • Catalytic asymmetric intermolecular Stetter reaction of enals with nitroalkenes: Enhancement of catalytic efficiency through bifunctional additives
    • DiRocco, D.A.; Rovis, T. Catalytic asymmetric intermolecular Stetter reaction of enals with nitroalkenes: Enhancement of catalytic efficiency through bifunctional additives. J. Am. Chem. Soc. 2011, 133, 10402-10405.
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 10402-10405
    • Dirocco, D.A.1    Rovis, T.2
  • 34
    • 79952764714 scopus 로고    scopus 로고
    • Synthesis of (1R, 2R)-DPEN-derived triazolium salts and their application in asymmetric intramolecular Stetter reactions
    • Jia, M.-Q.; Li, Y.; Rong, Z.-Q.; You, S.-L. Synthesis of (1R, 2R)-DPEN-derived triazolium salts and their application in asymmetric intramolecular Stetter reactions. Org. Biomol. Chem. 2011, 9, 2072-2074.
    • (2011) Org. Biomol. Chem. , vol.9 , pp. 2072-2074
    • Jia, M.-Q.1    Li, Y.2    Rong, Z.-Q.3    You, S.-L.4
  • 35
    • 79953171934 scopus 로고    scopus 로고
    • Mechanistic investigation of the enantioselective intramolecular Stetter reaction: Proton transfer is the first irreversible step
    • Moore, J.L.; Silvestri, A.P.; Read de Alaniz, J.; DiRocco, D.A.; Rovis, T. Mechanistic investigation of the enantioselective intramolecular Stetter reaction: Proton transfer is the first irreversible step. Org. Lett. 2011, 13, 1742-1745.
    • (2011) Org. Lett. , vol.13 , pp. 1742-1745
    • Moore, J.L.1    Silvestri, A.P.2    Read De Alaniz, J.3    Dirocco, D.A.4    Rovis, T.5
  • 36
    • 56049084681 scopus 로고    scopus 로고
    • The mechanism of the Stetter reaction - A DFT study
    • Hawkes, K.J.; Yates, B.F. The mechanism of the Stetter reaction - A DFT study. Eur. J. Org. Chem. 2008, 5563-5570.
    • (2008) Eur. J. Org. Chem. , pp. 5563-5570
    • Hawkes, K.J.1    Yates, B.F.2
  • 37
    • 48049104562 scopus 로고    scopus 로고
    • N-Heterocyclic carbene catalyzed intramolecular nucleophilic addition of carbonyl anion equivalents to enol ethers
    • He, J.; Tang, S.; Liu, J.; Su, Y.; Pan, X.; She, X. N-Heterocyclic carbene catalyzed intramolecular nucleophilic addition of carbonyl anion equivalents to enol ethers. Tetrahedron 2008, 64, 8797-8800.
    • (2008) Tetrahedron , vol.64 , pp. 8797-8800
    • He, J.1    Tang, S.2    Liu, J.3    Su, Y.4    Pan, X.5    She, X.6
  • 38
    • 79960586134 scopus 로고    scopus 로고
    • Quantum mechanical investigation of the effect of catalyst fluorination in the intermolecular asymmetric stetter reaction
    • Um, J.M.; DiRocco, D.A.; Noey, E.L.; Rovis, T.; Houk, K.N. Quantum mechanical investigation of the effect of catalyst fluorination in the intermolecular asymmetric stetter reaction. J. Am. Chem. Soc. 2011, 133, 11249-11254.
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 11249-11254
    • Um, J.M.1    Dirocco, D.A.2    Noey, E.L.3    Rovis, T.4    Houk, K.N.5
  • 39
    • 62549157772 scopus 로고    scopus 로고
    • Understanding the mechanism of the N-heterocyclic carbene-catalyzed ring-expansion of 4-formyl-[beta]-lactams to succinimide derivatives
    • Domingo, L.R.; Aurell, M.J.; Arnó, M. Understanding the mechanism of the N-heterocyclic carbene-catalyzed ring-expansion of 4-formyl-[beta]- lactams to succinimide derivatives. Tetrahedron 2009, 65, 3432-3440.
    • (2009) Tetrahedron , vol.65 , pp. 3432-3440
    • Domingo, L.R.1    Aurell, M.J.2    Arnó, M.3
  • 40
    • 77957925624 scopus 로고    scopus 로고
    • Understanding the mechanism of stereoselective synthesis of cyclopentenes via N-heterocyclic carbene catalyzed reactions of enals with enones
    • Domingo, L.R.; Zaragozá, R.J.; Arnó, M. Understanding the mechanism of stereoselective synthesis of cyclopentenes via N-heterocyclic carbene catalyzed reactions of enals with enones. Org. Biomol. Chem. 2010, 8, 4884-4891.
    • (2010) Org. Biomol. Chem. , vol.8 , pp. 4884-4891
    • Domingo, L.R.1    Zaragozá, R.J.2    Arnó, M.3
  • 41
    • 80052728555 scopus 로고    scopus 로고
    • Understanding the cooperative NHC/LA catalysis for stereoselective annulation reactions with homoenolates. A DFT study
    • Domingo, L.R.; Zaragozá, R.J.; Arnó, M. Understanding the cooperative NHC/LA catalysis for stereoselective annulation reactions with homoenolates. A DFT study. Org. Biomol. Chem. 2011, 9, 6616-6622.
    • (2011) Org. Biomol. Chem. , vol.9 , pp. 6616-6622
    • Domingo, L.R.1    Zaragozá, R.J.2    Arnó, M.3
  • 42
    • 0000189651 scopus 로고
    • Density-functional thermochemistry. III. The role of exact exchange
    • Becke, A.D. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 1993, 98, 5648-5652.
    • (1993) J. Chem. Phys. , vol.98 , pp. 5648-5652
    • Becke, A.D.1
  • 43
    • 0345491105 scopus 로고
    • Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
    • Lee, C.; Yang, W.; Parr, R.G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 1988, 37, 785-789.
    • (1988) Phys. Rev. B , vol.37 , pp. 785-789
    • Lee, C.1    Yang, W.2    Parr, R.G.3
  • 45
    • 84986439201 scopus 로고
    • Optimization of equilibrium geometries and transition structures
    • Schlegel, H.B. Optimization of equilibrium geometries and transition structures. J. Comput. Chem. 1982, 3, 214-218.
    • (1982) J. Comput. Chem. , vol.3 , pp. 214-218
    • Schlegel, H.B.1
  • 46
    • 84857546019 scopus 로고
    • Advanced series in physical chemistry
    • Yarkony, D.R., Ed.; World Scientific Publishing: Singapore
    • Schlegel, H.B. Advanced series in physical chemistry. In Modern Electronic Structure Theory, Yarkony, D.R., Ed.; World Scientific Publishing: Singapore, 1994; Volume 2.
    • (1994) Modern Electronic Structure Theory , vol.2
    • Schlegel, H.B.1
  • 47
    • 0004465903 scopus 로고
    • Formulation of the reaction coordinate
    • Fukui, K. Formulation of the reaction coordinate. J. Phys. Chem. 1970, 74, 4161-4163.
    • (1970) J. Phys. Chem. , vol.74 , pp. 4161-4163
    • Fukui, K.1
  • 48
    • 33750614386 scopus 로고
    • Reaction path following in mass-weighted internal coordinates
    • González, C.; Schlegel, H.B. Reaction path following in mass-weighted internal coordinates. J. Phys. Chem. 1990, 94, 5523-5527.
    • (1990) J. Phys. Chem. , vol.94 , pp. 5523-5527
    • González, C.1    Schlegel, H.B.2
  • 49
    • 36449008790 scopus 로고
    • Improved algorithms for reaction path following: Higher-order implicit algorithms
    • González, C.; Schlegel, H.B. Improved algorithms for reaction path following: Higher-order implicit algorithms. J. Chem. Phys. 1991, 95, 5853-5860.
    • (1991) J. Chem. Phys. , vol.95 , pp. 5853-5860
    • González, C.1    Schlegel, H.B.2
  • 50
    • 11744256643 scopus 로고
    • Molecular interactions in solution: An overview of methods based on continuous distributions of the solvent
    • Tomasi, J.; Persico, M. Molecular interactions in solution: An overview of methods based on continuous distributions of the solvent. Chem. Rev. 1994, 94, 2027-2094. (Pubitemid 124000195)
    • (1994) Chemical Reviews , vol.94 , Issue.7 , pp. 2027-2094
    • Tomasi, J.1    Persico, M.2
  • 52
    • 0031209054 scopus 로고    scopus 로고
    • A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to Isotropic and anisotropic dielectrics
    • Cances, E.; Mennucci, B.; Tomasi, J. A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics. J. Chem. Phys. 1997, 107, 3032-3041. (Pubitemid 127568923)
    • (1997) Journal of Chemical Physics , vol.107 , Issue.8 , pp. 3032-3041
    • Cances, E.1    Mennucci, B.2    Tomasi, J.3
  • 53
    • 84962359221 scopus 로고    scopus 로고
    • Ab initio study of solvated molecules: A new implementation of the polarizable continuum model
    • PII S0009261496003491
    • Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Ab initio study of solvated molecules: A new implementation of the polarizable continuum model. Chem. Phys. Lett. 1996, 255, 327-335. (Pubitemid 126163033)
    • (1996) Chemical Physics Letters , vol.255 , Issue.4-6 , pp. 327-335
    • Cossi, M.1    Barone, V.2    Cammi, R.3    Tomasi, J.4
  • 54
    • 84962428785 scopus 로고    scopus 로고
    • Geometry optimization of molecular structures in solution by the polarizable continuum model
    • Barone, V.; Cossi, M.; Tomasi, J. Geometry optimization of molecular structures in solution by the polarizable continuum model. J. Comput. Chem. 1998, 19, 404-417. (Pubitemid 128573764)
    • (1998) Journal of Computational Chemistry , vol.19 , Issue.4 , pp. 404-417
    • Barone, V.1    Cossi, M.2    Tomasi, J.3
  • 56
    • 0011083499 scopus 로고
    • Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint
    • Reed, A.E.; Curtiss, L.A.; Weinhold, F. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem. Rev. 1988, 88, 899-926.
    • (1988) Chem. Rev. , vol.88 , pp. 899-926
    • Reed, A.E.1    Curtiss, L.A.2    Weinhold, F.3
  • 58
    • 0027946619 scopus 로고
    • Classification of chemical bonds based on topological analysis of electron localization functions
    • DOI 10.1038/371683a0
    • Silvi, B.; Savin, A. Classification of chemical bonds based on topological analysis of electron localization functions. Nature 1994, 371, 683-686. (Pubitemid 24329613)
    • (1994) Nature , vol.371 , Issue.6499 , pp. 683-686
    • Silvi, B.1    Savin, A.2
  • 59
    • 0037009306 scopus 로고    scopus 로고
    • The synaptic order: A key concept to understand multicenter bonding
    • DOI 10.1016/S0022-2860(02)00231-4, PII S0022286002002314
    • Silvi, B. The synaptic order: A key concept to understand multicenter bonding. J. Mol. Struct. 2002, 614, 3-10. (Pubitemid 34987708)
    • (2002) Journal of Molecular Structure , vol.614 , Issue.1-3 , pp. 3-10
    • Silvi, B.1
  • 60
    • 0000393496 scopus 로고    scopus 로고
    • Computational tools for the electron localization function topological analysis
    • PII S009784859900039X
    • Noury, S.; Krokidis, X.; Fuster, F.; Silvi, B. Computational tools for the electron localization function topological analysis. Comput. Chem. 1999, 23, 597-604. (Pubitemid 129587941)
    • (1999) Computers and Chemistry , vol.23 , Issue.6 , pp. 597-604
    • Noury, S.1    Krokidis, X.2    Fuster, F.3    Silvi, B.4
  • 62
    • 0347291894 scopus 로고
    • Absolute hardness: Companion parameter to absolute electronegativity
    • Parr, R.G.; Pearson, R.G. Absolute hardness: Companion parameter to absolute electronegativity. J. Am. Chem. Soc. 1983, 105, 7512-7516.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 7512-7516
    • Parr, R.G.1    Pearson, R.G.2
  • 64
    • 45249094743 scopus 로고    scopus 로고
    • Understanding the reactivity of captodative ethylenes in polar cycloaddition reactions. A theoretical study
    • DOI 10.1021/jo800572a
    • Domingo, L.R.; Chamorro, E.; Pérez, P. Understanding the reactivity of captodative ethylenes in polar cycloaddition reactions. A theoretical study. J. Org. Chem. 2008, 73, 4615-4624. (Pubitemid 351842480)
    • (2008) Journal of Organic Chemistry , vol.73 , Issue.12 , pp. 4615-4624
    • Domingo, L.R.1    Chamorro, E.2    Perez, P.3
  • 65
    • 80053303867 scopus 로고    scopus 로고
    • The nucleophilicity N index in organic chemistry
    • Domingo, L.R.; Pérez, P. The nucleophilicity N index in organic chemistry. Org. Biomol. Chem. 2011, 9, 7168-7175.
    • (2011) Org. Biomol. Chem. , vol.9 , pp. 7168-7175
    • Domingo, L.R.1    Pérez, P.2
  • 66
    • 0042113153 scopus 로고
    • Self-consistent equations including exchange and correlation effects
    • Kohn, W.; Sham, L. Self-consistent equations including exchange and correlation effects. J. Phys. Rev. 1965, 140, 1133-1138.
    • (1965) J. Phys. Rev. , vol.140 , pp. 1133-1138
    • Kohn, W.1    Sham, L.2
  • 67
    • 0037173332 scopus 로고    scopus 로고
    • Quantitative characterization of the local electrophilicity of organic molecules. Understanding the regioselectivity on Diels-Alder reactions
    • DOI 10.1021/jp020715j
    • Domingo, L.R.; Aurell, M.J.; Pérez, P.; Contreras, R. Quantitative characterization of the local electrophilicity of organic molecules. Understanding the regioselectivity on Diels-Alder reactions. J. Phys. Chem. A 2002, 106, 6871-6875. (Pubitemid 35382661)
    • (2002) Journal of Physical Chemistry A , vol.106 , Issue.29 , pp. 6871-6875
    • Domingo, L.R.1    Aurell, M.J.2    Perez, P.3    Contreras, R.4
  • 68
    • 58349122051 scopus 로고    scopus 로고
    • A condensed-to-atom nucleophilicity index. An application to the director effects on the electrophilic aromatic substitutions
    • Pérez, P.; Domingo, L.R.; Duque-Noreña, M.; Chamorro, E. A condensed-to-atom nucleophilicity index. An application to the director effects on the electrophilic aromatic substitutions. J. Mol. Struct. (Theochem) 2009, 895, 86-91.
    • (2009) J. Mol. Struct. (Theochem) , vol.895 , pp. 86-91
    • Pérez, P.1    Domingo, L.R.2    Duque-Noreña, M.3    Chamorro, E.4
  • 69
    • 0042534101 scopus 로고
    • Density functional approach to the frontier-electron theory of chemical reactivity
    • Parr, R.G.; Yang, W. Density functional approach to the frontier-electron theory of chemical reactivity. J. Am. Chem. Soc. 1984, 106, 4049-4050.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 4049-4050
    • Parr, R.G.1    Yang, W.2
  • 70
    • 0001154851 scopus 로고    scopus 로고
    • A direct evaluation of regional Fukui functions in molecules
    • PII S0009261499003255
    • Contreras, R.; Fuentealba, P.; Galván, M.; Pérez, P. A direct evaluation of regional Fukui functions in molecules. Chem. Phys. Lett. 1999, 304, 405-413. (Pubitemid 129610834)
    • (1999) Chemical Physics Letters , vol.304 , Issue.5-6 , pp. 405-413
    • Contreras, R.R.1    Fuentealba, P.2    Galvan, M.3    Perez, P.4
  • 71
    • 84857551694 scopus 로고    scopus 로고
    • Understanding local electrophilicity/nucleophilicity activation through a single reactivity difference index
    • in press
    • Chattaraj, P.K.; Duley, S.; Domingo L.R. Understanding local electrophilicity/nucleophilicity activation through a single reactivity difference index. Org. Biomol. Chem. 2012, in press.
    • (2012) Org. Biomol. Chem.
    • Chattaraj, P.K.1    Duley, S.2    Domingo, L.R.3
  • 72
    • 0037181996 scopus 로고    scopus 로고
    • Quantitative characterization of the global electrophilicity power of common diene/dienophile pairs in Diels-Alder reactions
    • DOI 10.1016/S0040-4020(02)00410-6, PII S0040402002004106
    • Domingo, L.R.; Aurell, M.J.; Pérez, P.; Contreras, R. Quantitative characterization of the global electrophilicity of common diene/dienophile pairs in Diels-Alder reactions. Tetrahedron 2002, 58, 4417-4423. (Pubitemid 34522034)
    • (2002) Tetrahedron , vol.58 , Issue.22 , pp. 4417-4423
    • Domingo, L.R.1    Aurell, M.J.2    Perez, P.3    Contreras, R.4
  • 73
    • 50349093158 scopus 로고    scopus 로고
    • A further exploration of a nucleophilicity index based on the gas-phase ionization potentials
    • Jaramillo, P.; Domingo, L.R.; Chamorro, E.; Pérez, P. A further exploration of a nucleophilicity index based on the gas-phase ionization potentials. J. Mol. Struct. 2008, 865, 68-72.
    • (2008) J. Mol. Struct. , vol.865 , pp. 68-72
    • Jaramillo, P.1    Domingo, L.R.2    Chamorro, E.3    Pérez, P.4
  • 74
    • 77955122782 scopus 로고    scopus 로고
    • Quantitative characterization of group electrophilicity and nucleophilicity for intramolecular Diels-Alder reactions
    • Soto-Delgado, J.; Domingo, L.R.; Contreras, R. Quantitative characterization of group electrophilicity and nucleophilicity for intramolecular Diels-Alder reactions. Org. Biomol. Chem. 2010, 8, 3678-3683.
    • (2010) Org. Biomol. Chem. , vol.8 , pp. 3678-3683
    • Soto-Delgado, J.1    Domingo, L.R.2    Contreras, R.3
  • 75
    • 77958097193 scopus 로고    scopus 로고
    • Invariance of electrophilicity of independent fragments. Application to intramolecular Diels-Alder reactions
    • Soto-Delgado, J.; Aizman, A.; Domingo, L.R.; Contreras, R. Invariance of electrophilicity of independent fragments. Application to intramolecular Diels-Alder reactions. Chem. Phys. Lett. 2010, 499, 272-277.
    • (2010) Chem. Phys. Lett. , vol.499 , pp. 272-277
    • Soto-Delgado, J.1    Aizman, A.2    Domingo, L.R.3    Contreras, R.4
  • 76
    • 0041732169 scopus 로고    scopus 로고
    • The joint use of catastrophe theory and electron localization function to characterize molecular mechanisms. A density functional study of the Diels-Alder reaction
    • Berski, S.; Andrés, J.; Silvi, B.; Domingo, L.R. The joint use of catastrophe theory and electron localization function to characterize molecular mechanisms. A density functional study of the Diels-Alder reaction. J. Phys. Chem. A 2003, 107, 6014-6024.
    • (2003) J. Phys. Chem. A , vol.107 , pp. 6014-6024
    • Berski, S.1    Andrés, J.2    Silvi, B.3    Domingo, L.R.4
  • 77
    • 7044263244 scopus 로고    scopus 로고
    • Understanding the molecular mechanism of the 1,3-dipolar cycloaddition between fulminic acid and acetylene in terms of the electron localization function and catastrophe theory
    • Polo, V.; Andrés, J.; Castillo, R.; Berski, S.; Silvi, B. Understanding the molecular mechanism of the 1,3-dipolar cycloaddition between fulminic acid and acetylene in terms of the electron localization function and catastrophe theory. Chem. Eur. J. 2004, 10, 5165-5172.
    • (2004) Chem. Eur. J. , vol.10 , pp. 5165-5172
    • Polo, V.1    Andrés, J.2    Castillo, R.3    Berski, S.4    Silvi, B.5
  • 78
    • 33845545242 scopus 로고    scopus 로고
    • 1,3-Dipolar cycloadditions of electrophilically activated benzonitrile N-oxides. Polar cycloaddition versus oxime formation
    • DOI 10.1021/jo0613986
    • Domingo, L.R.; Picher, M.T.; Arroyo, P.; Sáez, J.A. 1,3-Dipolar cycloadditions of electrophilically activated benzonitrile N-oxides. Polar cycloaddition versus oxime formation. J. Org. Chem. 2006, 71, 9319-9330. (Pubitemid 44924513)
    • (2006) Journal of Organic Chemistry , vol.71 , Issue.25 , pp. 9319-9330
    • Domingo, L.R.1    Picher, M.T.2    Arroyo, P.3    Saez, J.A.4
  • 79
    • 33846434468 scopus 로고    scopus 로고
    • New findings on the Diels - Alder reactions. An analysis based on the bonding evolution theory
    • DOI 10.1021/jp068071t
    • Berski, S.; Andrés, J.; Silvi, B.; Domingo, L.R. New findings on the Diels-Alder reactions. An analysis based on the bonding evolution theory. J. Phys. Chem. A 2006, 110, 13939-13947. (Pubitemid 46137762)
    • (2006) Journal of Physical Chemistry A , vol.110 , Issue.51 , pp. 13939-13947
    • Berski, S.1    Andres, J.2    Silvi, B.3    Domingo, L.R.4
  • 80
    • 49649122819 scopus 로고    scopus 로고
    • Understanding reaction mechanisms in organic chemistry from catastrophe theory applied to the electron localization function topology
    • Polo, V.; Andrés, J.; Berski, S.; Domingo, L.R.; Silvi, B. Understanding reaction mechanisms in organic chemistry from catastrophe theory applied to the electron localization function topology. J. Phys. Chem. A 2008, 112, 7128-7136.
    • (2008) J. Phys. Chem. A , vol.112 , pp. 7128-7136
    • Polo, V.1    Andrés, J.2    Berski, S.3    Domingo, L.R.4    Silvi, B.5
  • 81
    • 78649507886 scopus 로고    scopus 로고
    • Understanding the high reactivity of the azomethine ylides in [3+2] cycloaddition reactions
    • Domingo, L.R.; Chamorro, E.; Pérez, P. Understanding the high reactivity of the azomethine ylides in [3+2] cycloaddition reactions. Lett. Org. Chem. 2010, 7, 432-439.
    • (2010) Lett. Org. Chem. , vol.7 , pp. 432-439
    • Domingo, L.R.1    Chamorro, E.2    Pérez, P.3
  • 82
    • 78651497656 scopus 로고    scopus 로고
    • Understanding the electronic reorganization along the nonpolar [3+2] cycloaddition reactions of carbonyl ylides
    • Domingo, L.R.; Sáez, J.A. Understanding the electronic reorganization along the nonpolar [3+2] cycloaddition reactions of carbonyl ylides. J. Org. Chem. 2011, 76, 373-379.
    • (2011) J. Org. Chem. , vol.76 , pp. 373-379
    • Domingo, L.R.1    Sáez, J.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.