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Volumn 16, Issue 3, 2010, Pages 836-847

From salts to ionic liquids by systematic structural modifications: A rational approach towards the efficient modular synthesis of enantiopure imidazolium salts

Author keywords

Chirality; Green chemistry; Imidazolium salts; Ionic liquids; Lipases

Indexed keywords

CHIRALITY; HYDROGEN BONDS; LIPASES; MELTING POINT; MIXTURES; POSITIVE IONS; SALTS; SINGLE CRYSTALS; SPECTROSCOPIC ANALYSIS; STEREOCHEMISTRY; TOPOLOGY; X RAY DIFFRACTION;

EID: 75249091879     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901623     Document Type: Article
Times cited : (49)

References (111)
  • 16
    • 0000034575 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2000, 39, 3772-3789
    • (2000) Angew. Chem. Int. Ed , vol.39 , pp. 3772-3789
  • 17
    • 0347417134 scopus 로고    scopus 로고
    • g) T. Welton, Chem. Rev. 1999, 99, 2071-2083.
    • (1999) Chem. Rev , vol.99 , pp. 2071-2083
    • Welton, T.1
  • 25
    • 38349078806 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 654 -670;
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 654-670
  • 33
    • 37349014528 scopus 로고    scopus 로고
    • M. Smiglak, A. Metlen, R. D. Rogers, Acc. Chem. Res. 2007, 40, 11821192.
    • b) M. Smiglak, A. Metlen, R. D. Rogers, Acc. Chem. Res. 2007, 40, 11821192.
  • 38
    • 53749100279 scopus 로고    scopus 로고
    • For general reviews of chiral ionic liquids, see: a
    • For general reviews of chiral ionic liquids, see: a) K. Bica, P. Gaert- ner, Eur. J. Org. Chem. 2008, 3235-3250
    • (2008) Eur. J. Org. Chem , pp. 3235-3250
    • Bica, K.1    Gaert- ner, P.2
  • 47
    • 53249131194 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 7339-7341;
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 7339-7341
  • 48
    • 51049107026 scopus 로고    scopus 로고
    • T. Yu, T. Yamada, G. C. Gaviola, R. G. Weiss, Chem. Mater. 2008, 20, 53375344;
    • c) T. Yu, T. Yamada, G. C. Gaviola, R. G. Weiss, Chem. Mater. 2008, 20, 53375344;
  • 55
    • 33746298422 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 3689-3692.
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 3689-3692
  • 66
    • 55349120515 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 8634-8637.
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 8634-8637
  • 69
    • 34250856228 scopus 로고    scopus 로고
    • Some preliminary synthetic results regarding the preparation of chiral imidazolium salts have been reported previously: E. Busto, N. Ríos-Lombardía, V. Gotor-Fernández, E. García- Verdugo, I. Alfonso, A. Menendez-Velázquez, S. Garcia-Granda, M. I. Burguete, S. V. Luis, V. Gotor, Tetrahedron Lett. 2007, 48, 5251 -5254
    • Some preliminary synthetic results regarding the preparation of chiral imidazolium salts have been reported previously: E. Busto, N. Ríos-Lombardía, V. Gotor-Fernández, E. García- Verdugo, I. Alfonso, A. Menendez-Velázquez, S. Garcia-Granda, M. I. Burguete, S. V. Luis, V. Gotor, Tetrahedron Lett. 2007, 48, 5251 -5254.
  • 70
    • 75249086318 scopus 로고    scopus 로고
    • See the Supporting Information for additional data
    • See the Supporting Information for additional data.
  • 72
    • 75249105450 scopus 로고    scopus 로고
    • The nomenclature of imidazolium salts is defined by seven descriptors: The first one includes the absolute configuration of C1 and C2 at the cycloalkyl ring [for instance: (S, S, The relative configuration at these carbon atoms is reported by the second descriptor trans or cis [for instance: (S, S, trans, The size of the cycloalkyl ring is described through the use of the terms Cy5 for cyclopentane rings and Cy6 for cyclohexane rings [for instance: (S, S)-trans-Cy5, The fourth descriptor indicates the presence of OH or OR at C2 of the cycloalkyl ring [for instance: (S, S)-trans-Cy5-OH, The nature of the alkyl chain at N3 of the imidazolium moiety is indicated by the use of Bn (for benzyl, Bu (for butyl, or Oct (for octyl, for instance: (S, S)-trans-Cy5-OH-Bu, Finally, the term Im refers to the central core of imidazolium, while the last descriptor refers to the specific anion included in the structure [for instance: (S, S)-tran
    • The nomenclature of imidazolium salts is defined by seven descriptors: The first one includes the absolute configuration of C1 and C2 at the cycloalkyl ring [for instance: (S, S)-]. The relative configuration at these carbon atoms is reported by the second descriptor trans or cis [for instance: (S, S)- trans]. The size of the cycloalkyl ring is described through the use of the terms Cy5 for cyclopentane rings and Cy6 for cyclohexane rings [for instance: (S, S)-trans-Cy5]. The fourth descriptor indicates the presence of OH or OR at C2 of the cycloalkyl ring [for instance: (S, S)-trans-Cy5-OH-]. The nature of the alkyl chain at N3 of the imidazolium moiety is indicated by the use of Bn (for benzyl), Bu (for butyl), or Oct (for octyl) [for instance: (S, S)-trans-Cy5-OH-Bu- ]. Finally, the term Im refers to the central core of imidazolium, while the last descriptor refers to the specific anion included in the structure [for instance: (S, S)-trans-Cy5-OH-Bu-Im-Cl].
  • 73
    • 75249097452 scopus 로고    scopus 로고
    • See the Supporting Information for a complete list of yields and T m's for all the ionic liquids prepared in this work
    • m's for all the ionic liquids prepared in this work.
  • 79
  • 84
    • 33746140041 scopus 로고    scopus 로고
    • J. Y. Z. Chiou, J. N. Chen, J. S. Lei, I. J. B. Lin, J. Mater. Chem. 2006, 16, 29722977.
    • d) J. Y. Z. Chiou, J. N. Chen, J. S. Lei, I. J. B. Lin, J. Mater. Chem. 2006, 16, 29722977.
  • 86
    • 53549132818 scopus 로고    scopus 로고
    • K. Fumino, A. Wulf, R. Ludwig, Angew. Chem. 2008, 120, 38903894; Angew. Chem. Int. Ed. 2008, 47, 3830-3834;
    • b) K. Fumino, A. Wulf, R. Ludwig, Angew. Chem. 2008, 120, 38903894; Angew. Chem. Int. Ed. 2008, 47, 3830-3834;
  • 96
    • 75249096211 scopus 로고    scopus 로고
    • K. Fumino, A. Wulf, R. Ludwig, Angew. Chem. 2008, 120, 88598862;
    • K. Fumino, A. Wulf, R. Ludwig, Angew. Chem. 2008, 120, 88598862;
  • 97
    • 55249105469 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 8731-8734.
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 8731-8734
  • 99
    • 75249105583 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 36393641;
    • Angew. Chem. Int. Ed. 2008, 47, 36393641;
  • 103
    • 75249102682 scopus 로고    scopus 로고
    • The computed vibrational frequencies of the C2-H bond for the obtained minima showed similar trends to the experimental ones (see the Supporting Information, Thus, the trans isomers showed absorptions at lower frequencies than the cis ones, in good accordance with the experimental data and reflecting the somehow stronger anion-cation interaction in the trans diastereoisomer. Although the computed (uncorrected) quantitative values of vibrational frequencies are far from the experimental ones, we believe that the correlation is qualitatively acceptable considering the number of approximations made
    • The computed vibrational frequencies of the C2-H bond for the obtained minima showed similar trends to the experimental ones (see the Supporting Information). Thus, the trans isomers showed absorptions at lower frequencies than the cis ones, in good accordance with the experimental data and reflecting the somehow stronger anion-cation interaction in the trans diastereoisomer. Although the computed (uncorrected) quantitative values of vibrational frequencies are far from the experimental ones, we believe that the correlation is qualitatively acceptable considering the number of approximations made.
  • 104
    • 75249086955 scopus 로고    scopus 로고
    • We also attempted to record circular dichroism spectra to further support these observations. Unfortunately, the very low UV absorption of the imidazolium group precluded suitable spectra from being obtained
    • We also attempted to record circular dichroism spectra to further support these observations. Unfortunately, the very low UV absorption of the imidazolium group precluded suitable spectra from being obtained.
  • 105
    • 75249087507 scopus 로고    scopus 로고
    • All these parameters were calculated with the Mercury 1.3.2 software, developed by The Cambridge Crystallographic Data Centre and freely downloadable at: www.ccdc.cam.ac.uk/products/mercury/.
    • All these parameters were calculated with the Mercury 1.3.2 software, developed by The Cambridge Crystallographic Data Centre and freely downloadable at: www.ccdc.cam.ac.uk/products/mercury/.
  • 107
    • 79960914053 scopus 로고    scopus 로고
    • The Lagrangian Approach to Chemistry: R. F. W. Bader, C. F. Matta, R. Boyd, in Quantum Theory of Atoms in Molecules: From Solid State to DNA and Drug Design, Wiley-VCH, Weinheim, 2007, pp. 37-59;
    • b) "The Lagrangian Approach to Chemistry": R. F. W. Bader, C. F. Matta, R. Boyd, in Quantum Theory of Atoms in Molecules: From Solid State to DNA and Drug Design, Wiley-VCH, Weinheim, 2007, pp. 37-59;
  • 109


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.