메뉴 건너뛰기




Volumn 36, Issue 12, 2010, Pages 978-985

Kinetic and thermodynamic study of the substituent effect on the amino-Claisen rearrangement of para-substituted N-allyl-N-arylamine: A Hammett study via DFT

Author keywords

amino Claisen rearrangement; density functional theory; Hammett; N allyl N arylamine; substituent effect

Indexed keywords

ARYL AMINES; CLAISEN REARRANGEMENT; DENSITY FUNCTIONALS; HAMMETT; SUBSTITUENT EFFECT;

EID: 78249237574     PISSN: 08927022     EISSN: 10290435     Source Type: Journal    
DOI: 10.1080/08927022.2010.497926     Document Type: Article
Times cited : (5)

References (23)
  • 1
    • 1242351495 scopus 로고    scopus 로고
    • Gas phase kinetics and mechanism of 2, 2-dimethyl but-3-enal and 1-methyl-6-methylenecyclohexa-2, 4-diene-1-carbaldehyde retro-cheletropic ene reaction
    • M. R. Gholami and M. Izadyar, Gas phase kinetics and mechanism of 2, 2-dimethyl but-3-enal and 1-methyl-6-methylenecyclohexa-2, 4-diene-1- carbaldehyde retro-cheletropic ene reaction, J. Mol. Struct. (THEOCHEM) 672(2004), pp. 61-66.
    • (2004) J. Mol. Struct. (THEOCHEM) , vol.672 , pp. 61-66
    • Gholami, M.R.1    Izadyar, M.2
  • 4
    • 0003376092 scopus 로고
    • Amino-Claisen rearrangements of N-vinylisoquinuclidenes in novel approaches to the synthesis of hydroisoquinolines and hydrophenanthridines
    • P. S. Mariano, D. D. Mariano, and P. L. Huesmann, Amino-Claisen rearrangements of N-vinylisoquinuclidenes in novel approaches to the synthesis of hydroisoquinolines and hydrophenanthridines, J. Org. Chem. 44(1979), pp. 124-133.
    • (1979) J. Org. Chem. , vol.44 , pp. 124-133
    • Mariano, P.S.1    Mariano, D.D.2    Huesmann, P.L.3
  • 8
    • 38149006408 scopus 로고    scopus 로고
    • Claisen rearrangement induced by low-energy collision of ESI-generated, protonated benzyloxy indoles
    • S. Crotti, L. Stella, I. Munari, F. Massaccesi, L. Cotarca, M. Forcato, and P. Traldi, Claisen rearrangement induced by low-energy collision of ESI-generated, protonated benzyloxy indoles, J. Mass Spectrom. 42(2007), pp. 1562-1568.
    • (2007) J. Mass Spectrom. , vol.42 , pp. 1562-1568
    • Crotti, S.1    Stella, L.2    Munari, I.3    Massaccesi, F.4    Cotarca, L.5    Forcato, M.6    Traldi, P.7
  • 9
    • 33845471185 scopus 로고
    • Catalysis of the Cope and Claisen rearrangements
    • R. P. Lutz, Catalysis of the Cope and Claisen rearrangements, Chem. Rev. 84(1984), pp. 205-247.
    • (1984) Chem. Rev. , vol.84 , pp. 205-247
    • Lutz, R.P.1
  • 10
    • 4344610661 scopus 로고    scopus 로고
    • Claisen rearrangement over the past nine decades
    • A. M. M. Castro, Claisen rearrangement over the past nine decades, Chem. Rev. 104(2004), pp. 2939-3002.
    • (2004) Chem. Rev. , vol.104 , pp. 2939-3002
    • Castro, A.M.M.1
  • 11
    • 64149113294 scopus 로고    scopus 로고
    • Heteropoly acids as useful recyclable heterogeneous catalysts for the facile and highly efficient aza-Cope rearrangement of N-allylanilines
    • A. Chaskar, V. Padalkar, K. Phatangare, K. Patil, A. Bodkhe, and B. Langi, Heteropoly acids as useful recyclable heterogeneous catalysts for the facile and highly efficient aza-Cope rearrangement of N-allylanilines, Appl. Catal. A: Gen. 359(2009), pp. 84-87.
    • (2009) Appl. Catal. A: Gen. , vol.359 , pp. 84-87
    • Chaskar, A.1    Padalkar, V.2    Phatangare, K.3    Patil, K.4    Bodkhe, A.5    Langi, B.6
  • 12
    • 0000410904 scopus 로고
    • Untersuchungen über aromatische amino-Claisen-Umlagerungen
    • S. Jolidon and H.-J. Hansen, Untersuchungen über aromatische amino-Claisen-Umlagerungen, Helv. Chim. Acta 60(1977), pp. 978-1032.
    • (1977) Helv. Chim. Acta , vol.60 , pp. 978-1032
    • Jolidon, S.1    Hansen, H.-J.2
  • 13
    • 0035970915 scopus 로고    scopus 로고
    • Investigation of the acidity constants and Hammett relations of some oxazolo[4, 5-b]pyridin derivatives using semiempirical AM1 quantum chemical calculation method
    • C. Öǧretir, E. Açíkkalp, and T. Güray, Investigation of the acidity constants and Hammett relations of some oxazolo[4, 5-b]pyridin derivatives using semiempirical AM1 quantum chemical calculation method, J. Mol. Struct. (THEOCHEM) 538(2001), pp. 107-116.
    • (2001) J. Mol. Struct. (THEOCHEM) , vol.538 , pp. 107-116
    • Öǧretir, C.1    Açíkkalp, E.2    Güray, T.3
  • 14
    • 30944464977 scopus 로고    scopus 로고
    • Geometry, solvent, and polar effects on the relationship between calculated core-electron binding energy shifts (ΔCEBE) and Hammett substituent (σ) constants
    • M. Segala, Y. Takahata, and D. P. Chong, Geometry, solvent, and polar effects on the relationship between calculated core-electron binding energy shifts (ΔCEBE) and Hammett substituent (σ) constants, J. Mol. Struct. (THEOCHEM) 758(2006), pp. 61-69.
    • (2006) J. Mol. Struct. (THEOCHEM) , vol.758 , pp. 61-69
    • Segala, M.1    Takahata, Y.2    Chong, D.P.3
  • 17
    • 4243553426 scopus 로고
    • Density-functional exchange-energy approximation with correct asymptotic behaviour
    • A. D. Becke, Density-functional exchange-energy approximation with correct asymptotic behaviour, Phys. Rev. A 38(1988), pp. 3098-3100.
    • (1988) Phys. Rev. A , vol.38 , pp. 3098-3100
    • Becke, A.D.1
  • 18
    • 0345491105 scopus 로고
    • Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
    • C. Lee, W. Yang, and R. G. Parr, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. B 37(1988), pp. 785-789.
    • (1988) Phys. Rev. B. , vol.37 , pp. 785-789
    • Lee, C.1    Yang, W.2    Parr, R.G.3
  • 19
    • 2442481958 scopus 로고    scopus 로고
    • Using redundant internal coordinates to optimize equilibrium geometries and transition states
    • H. B. Schlegel, C. Peng, P. Y. Ayala, and M. J. Frisch, Using redundant internal coordinates to optimize equilibrium geometries and transition states, J. Comput. Chem. 17(1996), pp. 49-56.
    • (1996) J. Comput. Chem. , vol.17 , pp. 49-56
    • Schlegel, H.B.1    Peng, C.2    Ayala, P.Y.3    Frisch, M.J.4
  • 22
    • 4544254546 scopus 로고    scopus 로고
    • Computational study on the effects of substituents and functional groups in the isomerization of 1-and 2-substituted propenes, acetaldimines, and aldehydes
    • C.-H. Chuang and M.-H. Lien, Computational study on the effects of substituents and functional groups in the isomerization of 1-and 2-substituted propenes, acetaldimines, and aldehydes, Eur. J. Org. Chem. 2004(2004), pp. 1432-1443.
    • (2004) Eur. J. Org. Chem. , vol.2004 , pp. 1432-1443
    • Chuang, C.-H.1    Lien, M.-H.2
  • 23
    • 26444501038 scopus 로고    scopus 로고
    • Quantum chemical topology (QCT) descriptors as substitutes for appropriate Hammett constants
    • P. J. Smith and P. L. A. Popelier, Quantum chemical topology (QCT) descriptors as substitutes for appropriate Hammett constants, Org. Biomol. Chem. 3(2005), pp. 3399-3407.
    • (2005) Org. Biomol. Chem. , vol.3 , pp. 3399-3407
    • Smith, P.J.1    Popelier, P.L.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.